September 30- October 11 2027
From the Acropolis and Parthenon in Athens to the crystal waters of
Milos and Paros, culminating in Santorini’s iconic caldera sunsets,
this 12-day journey blends the best of ancient history, island luxury, and curated local experiences.
With private guides, handpicked boutique stays, and unforgettable moments at every turn—from Epidaurus to Hydra and Mycenae—this is not just a trip, but the definitive way to experience Greece at its most breathtaking!
Milos and Paros, culminating in Santorini’s iconic caldera sunsets,
this 12-day journey blends the best of ancient history, island luxury, and curated local experiences.
With private guides, handpicked boutique stays, and unforgettable moments at every turn—from Epidaurus to Hydra and Mycenae—this is not just a trip, but the definitive way to experience Greece at its most breathtaking!
Pre-tour
September 29 2027
Wednesday
Leave the US
Overnight aboard your flight
September 29 2027
Wednesday
Leave the US
Overnight aboard your flight
Day One
September 30 2027
Thursday
Athens
Acropolis
Parthenon
Welcome to Athens, the birthplace of democracy—where your journey begins. Your hotel is ideally located near the New Acropolis Museum, widely regarded as one of the finest museums in the world, celebrated for both its remarkable collection and striking architecture. From here, you’ll enjoy spectacular views of the Acropolis and the Parthenon.
We recommend taking your time exploring the museum; skip-the-line tickets can be arranged upon request for a more seamless visit.
In the afternoon, meet your private guide to begin your exploration of the Acropolis. Stroll through the surrounding hills before ascending the “Sacred Rock” to experience the Parthenon—an enduring masterpiece of ancient architecture and a UNESCO World Heritage Site dating back to 447 BC. Take in sweeping views over Athens as you explore at a relaxed pace. Our walk concludes in the lively, winding streets of Monastiraki, one of the city’s oldest and most vibrant marketplaces.
Enjoy some time to rest before gathering again in the evening for a welcome drink and proper introductions. The day concludes with a special first-night dinner at a nearby traditional taverna.
Includes:
September 30 2027
Thursday
Athens
Acropolis
Parthenon
Welcome to Athens, the birthplace of democracy—where your journey begins. Your hotel is ideally located near the New Acropolis Museum, widely regarded as one of the finest museums in the world, celebrated for both its remarkable collection and striking architecture. From here, you’ll enjoy spectacular views of the Acropolis and the Parthenon.
We recommend taking your time exploring the museum; skip-the-line tickets can be arranged upon request for a more seamless visit.
In the afternoon, meet your private guide to begin your exploration of the Acropolis. Stroll through the surrounding hills before ascending the “Sacred Rock” to experience the Parthenon—an enduring masterpiece of ancient architecture and a UNESCO World Heritage Site dating back to 447 BC. Take in sweeping views over Athens as you explore at a relaxed pace. Our walk concludes in the lively, winding streets of Monastiraki, one of the city’s oldest and most vibrant marketplaces.
Enjoy some time to rest before gathering again in the evening for a welcome drink and proper introductions. The day concludes with a special first-night dinner at a nearby traditional taverna.
Includes:
- New Acropolis Museum (tickets optional)
- Private guided tour of the Acropolis
- Visit to the Parthenon (UNESCO World Heritage Site)
- Skip-the-line timed ticket entry to the Acropolis/ Parthenon
- Welcome drink
- Welcome dinner at a local taverna
- Two experienced tour leaders
- Hotel accommodation in Athens with rooftop bar, Acropolis views, and jacuzzi
- Overnight in Athens
This is an example of the style and standard of accommodation you may expect in Athens.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Day Two
October 1 2027
Corinth Canal
Epidaurous
Ermione
This morning, our private driver will pick us up as we set off for the legendary region of the Peloponnese. Along the way, we’ll stop at the Corinth Canal—an impressive engineering feat completed in the 1870s that dramatically cuts through the narrow isthmus. We’ll take some time here to enjoy a coffee or refreshing drink before continuing our journey.
Our next stop is the remarkable site of Epidaurus UNESCO World Heritage Site Asklepios at Epidaurous, renowned in antiquity as both a healing sanctuary and home to one of the most perfectly preserved ancient theaters in the world. This UNESCO World Heritage Site, the Sanctuary of Asclepius, has hosted performances for centuries—including those by the legendary Maria Callas—and still welcomes audiences during summer festivals. If we’re feeling inspired, we can step onto the stage and test its famous acoustics with a poem of our own.
After exploring the museum and ruins at a relaxed pace, we’ll continue on to Ermioni, a charming seaside town set on a pine-covered peninsula and surrounded by crystal-clear waters.
Once we’ve checked into our boutique hotel, we’ll have some free time to unwind. We can take a swim just steps away, stroll along the waterfront, or relax with a cocktail at a seaside café.
If time allows we can go and see one of our favorite olive oil producer. He will take us to one of the oldest olive trees in the entire area, one that is over 1200 years old and still producing. Then we will get to taste test his olive oil.
In the evening, we’ll gather for dinner at one of our favorite local tavernas, right by the water.
Includes:
October 1 2027
Corinth Canal
Epidaurous
Ermione
This morning, our private driver will pick us up as we set off for the legendary region of the Peloponnese. Along the way, we’ll stop at the Corinth Canal—an impressive engineering feat completed in the 1870s that dramatically cuts through the narrow isthmus. We’ll take some time here to enjoy a coffee or refreshing drink before continuing our journey.
Our next stop is the remarkable site of Epidaurus UNESCO World Heritage Site Asklepios at Epidaurous, renowned in antiquity as both a healing sanctuary and home to one of the most perfectly preserved ancient theaters in the world. This UNESCO World Heritage Site, the Sanctuary of Asclepius, has hosted performances for centuries—including those by the legendary Maria Callas—and still welcomes audiences during summer festivals. If we’re feeling inspired, we can step onto the stage and test its famous acoustics with a poem of our own.
After exploring the museum and ruins at a relaxed pace, we’ll continue on to Ermioni, a charming seaside town set on a pine-covered peninsula and surrounded by crystal-clear waters.
Once we’ve checked into our boutique hotel, we’ll have some free time to unwind. We can take a swim just steps away, stroll along the waterfront, or relax with a cocktail at a seaside café.
If time allows we can go and see one of our favorite olive oil producer. He will take us to one of the oldest olive trees in the entire area, one that is over 1200 years old and still producing. Then we will get to taste test his olive oil.
In the evening, we’ll gather for dinner at one of our favorite local tavernas, right by the water.
Includes:
- Full breakfast
- Private driver and luxury transportation
- Visit to the Corinth Canal
- Entrance fees and visit to Epidaurus and the Sanctuary of Asclepius (UNESCO World Heritage Site)
- Boutique hotel in Ermioni, centrally located by the sea
- Olive oil producer, old olive tree and taste testing (if time allows us)
- Dinner at a seaside taverna
- Two experienced tour leaders
- Overnight in Ermioni
Day Three
October 2 2027
Island of Hydra
Ermione
Enjoy a leisurely breakfast before we set off on a day trip (no need to pack your bags) to the enchanting island of Hydra, traveling by hydrofoil. With no roads or cars, Hydra has preserved its traditional charm, featuring elegant neoclassical homes that cascade amphitheater-style around the picturesque port.
Upon arrival, we’ll explore the island’s highlights, including a tour of a historic captain’s house. You’ll also have time to wander its charming streets and soak in the serene atmosphere. For lunch, we’ll provide excellent recommendations so you can savor the island’s local cuisine at your own pace.
In the afternoon, we board the ferry back to Ermione. The evening is yours to enjoy, with plenty of dining suggestions from us to help you make the most of your night.
Included in Your Experience:
October 2 2027
Island of Hydra
Ermione
Enjoy a leisurely breakfast before we set off on a day trip (no need to pack your bags) to the enchanting island of Hydra, traveling by hydrofoil. With no roads or cars, Hydra has preserved its traditional charm, featuring elegant neoclassical homes that cascade amphitheater-style around the picturesque port.
Upon arrival, we’ll explore the island’s highlights, including a tour of a historic captain’s house. You’ll also have time to wander its charming streets and soak in the serene atmosphere. For lunch, we’ll provide excellent recommendations so you can savor the island’s local cuisine at your own pace.
In the afternoon, we board the ferry back to Ermione. The evening is yours to enjoy, with plenty of dining suggestions from us to help you make the most of your night.
Included in Your Experience:
- Full Breakfast
- Walking tour of Hydra
- Round-trip ferry to Hydra and back
- Entrance fee and tour of a traditional captain’s house
- Lunch recommendations
- Dinner recommendations and reservations
- Two experienced tour leaders
- Boutique hotel in Ermioni, centrally located by the sea
- Overnight Ermione
This is an example of the style and standard of accommodation you may expect in Ermione.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Day Four
October 3 2027
Palamidi Fortress
Acronafplia
Nafplio
Savor breakfast and enjoy one last leisurely stroll along the waterfront of Ermioni, breathing in the sea air before your private driver arrives to take you to Nafplio—Greece’s first capital and one of its most elegant seaside towns. With its neoclassical architecture, fortress-topped hills, and vibrant waterfront promenades, Nafplio feels like a living postcard.
On arrival, we head directly to the hilltop strongholds of Palamidi Fortress and Acronafplia. From here, you’ll take in sweeping panoramic views over the Argolic Gulf and the red-tiled rooftops of the old town below.
Afterwards, we continue to your boutique hotel for check-in.
The afternoon is yours to enjoy at a relaxed pace—perhaps a swim at a nearby beach, a drink in the lively main square, or some leisurely shopping through Nafplio’s charming streets as the town gently comes to life.
We’ll be on hand to guide your explorations and, of course, to point you toward one of the town’s best local specialties—gelato, a beloved treat here.
As evening approaches, we’ll meet in the hotel lobby for a short walk through the atmospheric backstreets to a traditional taverna, where you’ll enjoy a memorable dinner in an intimate and authentic setting.
Included in Your Experience:
October 3 2027
Palamidi Fortress
Acronafplia
Nafplio
Savor breakfast and enjoy one last leisurely stroll along the waterfront of Ermioni, breathing in the sea air before your private driver arrives to take you to Nafplio—Greece’s first capital and one of its most elegant seaside towns. With its neoclassical architecture, fortress-topped hills, and vibrant waterfront promenades, Nafplio feels like a living postcard.
On arrival, we head directly to the hilltop strongholds of Palamidi Fortress and Acronafplia. From here, you’ll take in sweeping panoramic views over the Argolic Gulf and the red-tiled rooftops of the old town below.
Afterwards, we continue to your boutique hotel for check-in.
The afternoon is yours to enjoy at a relaxed pace—perhaps a swim at a nearby beach, a drink in the lively main square, or some leisurely shopping through Nafplio’s charming streets as the town gently comes to life.
We’ll be on hand to guide your explorations and, of course, to point you toward one of the town’s best local specialties—gelato, a beloved treat here.
As evening approaches, we’ll meet in the hotel lobby for a short walk through the atmospheric backstreets to a traditional taverna, where you’ll enjoy a memorable dinner in an intimate and authentic setting.
Included in Your Experience:
- Full breakfast
- Late morning departure
- Private luxury transfer from Ermioni to Nafplio
- Skip-the-line access to Palamidi Fortress and Acronafplia
- Two experienced tour leaders
- Boutique centrally located hotel in Nafplio
- Group dinner in Nafplio
- Overnight stay in Nafplio
Day Five
October 4 2027
Mycenae
Nemea
Nafplio
This morning, we’ll set out early with our private driver as we journey into the countryside toward the legendary city of Mycenae—the fabled home of King Agamemnon and Queen Clytemnestra. It was here that archaeologist Heinrich Schliemann believed he uncovered the famed “Mask of Agamemnon,” a discovery that captivated the world.
Our route winds through rolling hills and valleys dotted with shimmering olive groves, leading us to this extraordinary archaeological site. Once there, we’ll explore the awe-inspiring beehive tombs, massive cyclopean walls, and the on-site museum, where the rich history of Mycenae comes vividly to life.
We’ll pause for lunch on our own at a nearby taverna before continuing on to Nemea, a region steeped in both mythology and history. According to legend, this is where Hercules completed one of his twelve labors by slaying the Nemean Lion. Once a rival to Olympia, the ancient stadium and surrounding ruins offer a fascinating glimpse into Greece’s athletic and cultural past.
In the afternoon, we’ll visit a local winery to sample some of the region’s renowned wines.
Afterward, our driver will return us to Nafplio, where you’ll have the evening free. We’ll be happy to recommend a variety of excellent tavernas and restaurants—some right by the sea—for dinner at your leisure.
Included in Your Experience:
October 4 2027
Mycenae
Nemea
Nafplio
This morning, we’ll set out early with our private driver as we journey into the countryside toward the legendary city of Mycenae—the fabled home of King Agamemnon and Queen Clytemnestra. It was here that archaeologist Heinrich Schliemann believed he uncovered the famed “Mask of Agamemnon,” a discovery that captivated the world.
Our route winds through rolling hills and valleys dotted with shimmering olive groves, leading us to this extraordinary archaeological site. Once there, we’ll explore the awe-inspiring beehive tombs, massive cyclopean walls, and the on-site museum, where the rich history of Mycenae comes vividly to life.
We’ll pause for lunch on our own at a nearby taverna before continuing on to Nemea, a region steeped in both mythology and history. According to legend, this is where Hercules completed one of his twelve labors by slaying the Nemean Lion. Once a rival to Olympia, the ancient stadium and surrounding ruins offer a fascinating glimpse into Greece’s athletic and cultural past.
In the afternoon, we’ll visit a local winery to sample some of the region’s renowned wines.
Afterward, our driver will return us to Nafplio, where you’ll have the evening free. We’ll be happy to recommend a variety of excellent tavernas and restaurants—some right by the sea—for dinner at your leisure.
Included in Your Experience:
- Full breakfast
- Private driver
- Luxury private transportation
- Entrance fees and visit to Mycenae (UNESCO World Heritage Site) with skip-the-line access
- Entrance fees to Nemea and its ancient stadium (European Heritage List) with skip-the-line access
- Wine tasting at a local Nemean winery
- Two experienced tour leaders
- Dinner recommendations and reservations
- Overnight stay in Nafplio
This is an example of the style and standard of accommodation you may expect in Nafplio.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Day Six
October 5 2027
Island of Milos
Our private coach will take us to the airport for a short 40-minute flight to the island of Milos, set in the heart of the Cyclades.
Consistently ranked among the world’s most beautiful islands by Travel + Leisure, Milos remains one of Greece’s true gems—known for its striking landscapes, laid-back atmosphere, and rich history. It was here, in 1820, that the iconic Venus de Milo—now housed in the Louvre Museum in Paris—was discovered.
Upon arrival, we’ll settle into one of the island’s most charming seaside villages, where whitewashed houses, colorful fishing boats, and crystal-clear waters create an unmistakably Cycladic setting. Milos is especially renowned for its extraordinary coastline, shaped by volcanic activity and home to some of the most unique beaches in Greece. From the dramatic sea caves of Kleftiko and Sykia to the moonlike white rock formations of Sarakiniko, the island offers endless opportunities to explore and unwind.
Take some time to let the rhythm of the island sink in—perhaps with a refreshing swim, a walk along the harbor, or simply relaxing by the sea. For those feeling more adventurous, optional activities such as kayaking and snorkeling offer a closer look at Milos’ hidden coves and turquoise waters.
In the evening, we’ll come together for dinner, enjoying fresh local specialties in a beautiful island setting.
Includes:
October 5 2027
Island of Milos
Our private coach will take us to the airport for a short 40-minute flight to the island of Milos, set in the heart of the Cyclades.
Consistently ranked among the world’s most beautiful islands by Travel + Leisure, Milos remains one of Greece’s true gems—known for its striking landscapes, laid-back atmosphere, and rich history. It was here, in 1820, that the iconic Venus de Milo—now housed in the Louvre Museum in Paris—was discovered.
Upon arrival, we’ll settle into one of the island’s most charming seaside villages, where whitewashed houses, colorful fishing boats, and crystal-clear waters create an unmistakably Cycladic setting. Milos is especially renowned for its extraordinary coastline, shaped by volcanic activity and home to some of the most unique beaches in Greece. From the dramatic sea caves of Kleftiko and Sykia to the moonlike white rock formations of Sarakiniko, the island offers endless opportunities to explore and unwind.
Take some time to let the rhythm of the island sink in—perhaps with a refreshing swim, a walk along the harbor, or simply relaxing by the sea. For those feeling more adventurous, optional activities such as kayaking and snorkeling offer a closer look at Milos’ hidden coves and turquoise waters.
In the evening, we’ll come together for dinner, enjoying fresh local specialties in a beautiful island setting.
Includes:
- Full breakfast
- Flight to Milos
- Airport transfer to hotel
- Stay in a seaside village in the heart of Milos
- Dinner together featuring local cuisine
- Two experienced tour leaders
- Boutique hotel accommodation
- Overnight on the island of Milos
Day Seven
October 6 2027
Milos
Enjoy a relaxed morning at your own pace—sleep in, take an early stroll through town, or linger over a leisurely breakfast by the sea.
In the early afternoon, join us for an island tour as we explore some of Milos’s more remote and beautiful beaches, followed by time in the capital to browse its charming shops and cafés. If you prefer, you’re welcome to remain in the main town (Chora) and enjoy dinner independently—we’ll be happy to provide tailored recommendations and assist with reservations.
Included Experiences:
October 6 2027
Milos
Enjoy a relaxed morning at your own pace—sleep in, take an early stroll through town, or linger over a leisurely breakfast by the sea.
In the early afternoon, join us for an island tour as we explore some of Milos’s more remote and beautiful beaches, followed by time in the capital to browse its charming shops and cafés. If you prefer, you’re welcome to remain in the main town (Chora) and enjoy dinner independently—we’ll be happy to provide tailored recommendations and assist with reservations.
Included Experiences:
- Full breakfast
- Leisurely morning at your seaside hotel
- Stay in a seaside village in the heart of Milos
- Afternoon island tour featuring Milos’s iconic beaches and the main town
- Personalized dinner recommendations and reservations
- Two experienced tour leaders
- Boutique hotel accommodation
This is an example of the style and standard of accommodation you may expect on Milos.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Day Eight
October 7 2027
Island of Paros
Another beautiful day unfolds on the Aegean Sea. This morning, a private driver will collect us from the hotel and transfer us to the port, where we board our ferry to the island of Paros (approximately 2 hours).
Upon arrival, we’ll be greeted by another private driver and transferred to the picturesque seaside town of Naoussa, renowned for its charming harbor, traditional tavernas, and relaxed island atmosphere.
After check-in, we’ll set out on a gentle walk through the village, visiting quaint churches and wandering the narrow back streets that give Naoussa its unique character.
The afternoon is yours to enjoy—perhaps unwind by the pool with a refreshing drink or take in the seaside ambiance at your own pace.
Join us a little before dinner as we enjoy a cooking demonstration. We'll be making a few Greek mezedes (small plate appetizers) such as Tzatziki (yogurt dip) and Skordalia (garlic dip) and we will be sampling them to our heart's content. Later in the evening, join us for a memorable dinner together at a local taverna.
Included Experiences:
October 7 2027
Island of Paros
Another beautiful day unfolds on the Aegean Sea. This morning, a private driver will collect us from the hotel and transfer us to the port, where we board our ferry to the island of Paros (approximately 2 hours).
Upon arrival, we’ll be greeted by another private driver and transferred to the picturesque seaside town of Naoussa, renowned for its charming harbor, traditional tavernas, and relaxed island atmosphere.
After check-in, we’ll set out on a gentle walk through the village, visiting quaint churches and wandering the narrow back streets that give Naoussa its unique character.
The afternoon is yours to enjoy—perhaps unwind by the pool with a refreshing drink or take in the seaside ambiance at your own pace.
Join us a little before dinner as we enjoy a cooking demonstration. We'll be making a few Greek mezedes (small plate appetizers) such as Tzatziki (yogurt dip) and Skordalia (garlic dip) and we will be sampling them to our heart's content. Later in the evening, join us for a memorable dinner together at a local taverna.
Included Experiences:
- Breakfast
- Private transfer from hotel to Milos port
- Ferry from Milos to Paros (approx. 2 hours)
- Private transfer from Paros port to Naoussa
- Guided walk of Naoussa village
- Leisure time / beach or pool relaxation
- Cooking demonstration for Greek mezedes (small plate appetizers)
- Group dinner at a local taverna
- Two experienced tour leaders
- Boutique hotel accommodation
Day Nine
October 8 2027
Day around the island
Island of Paros
This morning, we set out to explore the island of Paros. On our way toward the main town, we’ll pause at the historic marble quarries, where the renowned Parian marble was once extracted—highly prized in antiquity and used for masterpieces such as the Medici Venus (Uffizi Gallery), the Nike of Samothrace (Louvre Museum), and the Venus de Milo (Louvre Museum).
From here, we continue into the island’s hilltop villages, where whitewashed houses, vibrant bougainvillea, and sweeping views create a quintessential Cycladic landscape. We’ll pause for a coffee and take in the scenery.
We will also make time to stop at and olive oil producer so that we can taste test some olives and olive oil. On the way there, we will stop at several olive trees believed to be 1500 years old and still producing.
Midday, we’ll visit a seaside village where you can enjoy lunch at your leisure at a traditional taverna.
The afternoon is free to relax as you wish—unwind by the pool, watch yachts drift into the harbor, or explore charming backstreets for some excellent shopping.
Dinner is on your own this evening, with plenty of wonderful seaside options to choose from.
Included Experiences:
October 8 2027
Day around the island
Island of Paros
This morning, we set out to explore the island of Paros. On our way toward the main town, we’ll pause at the historic marble quarries, where the renowned Parian marble was once extracted—highly prized in antiquity and used for masterpieces such as the Medici Venus (Uffizi Gallery), the Nike of Samothrace (Louvre Museum), and the Venus de Milo (Louvre Museum).
From here, we continue into the island’s hilltop villages, where whitewashed houses, vibrant bougainvillea, and sweeping views create a quintessential Cycladic landscape. We’ll pause for a coffee and take in the scenery.
We will also make time to stop at and olive oil producer so that we can taste test some olives and olive oil. On the way there, we will stop at several olive trees believed to be 1500 years old and still producing.
Midday, we’ll visit a seaside village where you can enjoy lunch at your leisure at a traditional taverna.
The afternoon is free to relax as you wish—unwind by the pool, watch yachts drift into the harbor, or explore charming backstreets for some excellent shopping.
Dinner is on your own this evening, with plenty of wonderful seaside options to choose from.
Included Experiences:
- Breakfast
- Day tour of Paros
- Visit to the historic marble quarries
- Exploration of mountain and seaside villages
- Olive oil taste testing
- Ancient olive trees
- Two experienced tour leaders
- Dinner recommendations and reservation assistance
- Caldera-view boutique hotel accommodation
This is an example of the style and standard of accommodation you may expect on Paros.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Day Ten
October 9 2027
Island of Santorini
Life along the caldera
You can have one more walk around the lovely village of Naoussa on Paros before we pack our bags and head to the port. We are off on our 2 hour ferry to Santorini—one of the most striking and unique destinations in the Aegean. Onboard, you will have access to cafes and bistros for lunch while we 'set sail'.
As we arrive, you’ll immediately notice the island’s dramatic landscape: whitewashed houses perched along the rim of the caldera, formed by a massive volcanic eruption around 1600 BC—one of the largest in recorded history. This eruption reshaped the island and is even thought by some to have inspired the legend of Atlantis. Today, the steep cliffs offer some of the most breathtaking views in all of Greece.
Our private driver will meet us at the port and transfer us to our hotel, perfectly situated along the caldera’s edge.
After settling in and dropping off your bags, take some time to unwind—perhaps enjoy a swim or sip a drink while taking in the panoramic views of the Aegean Sea. We will also head up an orientation walk of the nearby town of Oia, for those who want a little more activity.
Later in the evening enjoy the town on your own. We will have several restaurants to recommend and help with reservations if you want.
Included Experiences:
October 9 2027
Island of Santorini
Life along the caldera
You can have one more walk around the lovely village of Naoussa on Paros before we pack our bags and head to the port. We are off on our 2 hour ferry to Santorini—one of the most striking and unique destinations in the Aegean. Onboard, you will have access to cafes and bistros for lunch while we 'set sail'.
As we arrive, you’ll immediately notice the island’s dramatic landscape: whitewashed houses perched along the rim of the caldera, formed by a massive volcanic eruption around 1600 BC—one of the largest in recorded history. This eruption reshaped the island and is even thought by some to have inspired the legend of Atlantis. Today, the steep cliffs offer some of the most breathtaking views in all of Greece.
Our private driver will meet us at the port and transfer us to our hotel, perfectly situated along the caldera’s edge.
After settling in and dropping off your bags, take some time to unwind—perhaps enjoy a swim or sip a drink while taking in the panoramic views of the Aegean Sea. We will also head up an orientation walk of the nearby town of Oia, for those who want a little more activity.
Later in the evening enjoy the town on your own. We will have several restaurants to recommend and help with reservations if you want.
Included Experiences:
- Breakfast
- Private transfer to the port in Milos
- Ferry from Milos to Santorini
- Private transfer to our caldera-view hotel on Santorini
- Orientation walk
- Dinner recommendations and reservation assistance
- Caldera-view boutique hotel accommodation
Day Eleven
October 10 2027
Caldera Walk
Prehistoric Museum of Thera
Island of Santorini
Enjoy a leisurely breakfast as you gaze out over the deep blue Aegean, with volcanic islands rising in the distance.
Today, you have two wonderful ways to experience Santorini. You may choose to explore independently, browsing the island’s main villages—famed for their whitewashed architecture, boutique shops, and local crafts. Or, join us for a spectacular walk along the caldera, a dramatic cliffside path formed by one of the largest volcanic eruptions in history (around 1600 BC). Along the way, you’ll take in sweeping views of the submerged crater that gives Santorini its unmistakable shape.
Our routes lead us to Fira, the island’s lively capital, where we’ll visit the Prehistoric Museum of Thera. Here, we’ll explore extraordinary artifacts uncovered at Akrotiri—a remarkably advanced Bronze Age settlement preserved beneath volcanic ash. Some of these finds predate the Parthenon by over a thousand years and reveal a sophisticated society with multi-story buildings, vivid frescoes, and even early indoor plumbing. The sudden destruction of this thriving town has led many to associate it with the legend of Atlantis.
Lunch is on your own today—perhaps at one of Fira’s inviting cafés, where you can relax and soak in the views.
This afternoon is free for you to enjoy at your own pace.
Join us before dinner as we travel to a nearby winery well known for its innovative ideas to oenology and viticulture that elevated Santorini’s wines to international stardom. We will view their vines, some trellised and some woven in the traditional Santorini 'basket'. We will have a taste testing with some of their best vintages.
Join us later as we celebrate the journey together, raising a final toast and sharing one more memorable evening over the exceptional cuisine of Greece.
Included Experiences:
October 10 2027
Caldera Walk
Prehistoric Museum of Thera
Island of Santorini
Enjoy a leisurely breakfast as you gaze out over the deep blue Aegean, with volcanic islands rising in the distance.
Today, you have two wonderful ways to experience Santorini. You may choose to explore independently, browsing the island’s main villages—famed for their whitewashed architecture, boutique shops, and local crafts. Or, join us for a spectacular walk along the caldera, a dramatic cliffside path formed by one of the largest volcanic eruptions in history (around 1600 BC). Along the way, you’ll take in sweeping views of the submerged crater that gives Santorini its unmistakable shape.
Our routes lead us to Fira, the island’s lively capital, where we’ll visit the Prehistoric Museum of Thera. Here, we’ll explore extraordinary artifacts uncovered at Akrotiri—a remarkably advanced Bronze Age settlement preserved beneath volcanic ash. Some of these finds predate the Parthenon by over a thousand years and reveal a sophisticated society with multi-story buildings, vivid frescoes, and even early indoor plumbing. The sudden destruction of this thriving town has led many to associate it with the legend of Atlantis.
Lunch is on your own today—perhaps at one of Fira’s inviting cafés, where you can relax and soak in the views.
This afternoon is free for you to enjoy at your own pace.
Join us before dinner as we travel to a nearby winery well known for its innovative ideas to oenology and viticulture that elevated Santorini’s wines to international stardom. We will view their vines, some trellised and some woven in the traditional Santorini 'basket'. We will have a taste testing with some of their best vintages.
Join us later as we celebrate the journey together, raising a final toast and sharing one more memorable evening over the exceptional cuisine of Greece.
Included Experiences:
- Breakfast
- Optional independent shopping in Santorini’s main villages
- Optional caldera walk
- Visit to the Prehistoric Museum of Thera
- Exploration of Fira
- Visit to a local winery-one of the oldest on the island-for a taste testing.
- Farewell dinner together
This is an example of the style and standard of accommodation you may expect on Santorini.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Day Twelve
October 11 2027
Leave for the US
We bid you farewell this morning, or as the Greeks warmly say, “Kalo Taxidi”—may you have a safe and wonderful onward journey, carrying home unforgettable memories of your time in Greece.
Includes:
October 11 2027
Leave for the US
We bid you farewell this morning, or as the Greeks warmly say, “Kalo Taxidi”—may you have a safe and wonderful onward journey, carrying home unforgettable memories of your time in Greece.
Includes:
- Morning departure assistance
- Breakfast (if applicable)
- Hotel check-out support
- Farewell assistance and transfer help
What is included
This is a private custom trip lead by two tourleaders for 26 years leading tours.
All that is listed in the itinerary above is included.
-Private drivers
-Private Archaeological guides for multiple sites
-Skip-the-line tickets
-Dinners together where indicated, with wonderful food choices and red or white wines included
-Cooking lesson
-Breakfast in each hotel (full)
-Flight (with 50 lb luggage accepted)
-Ferries
-Winery
-Enjoying the activities with your private group
-Pre-tour Zoom meetings
-Your own Passport Page, along with eight supporting documents, all exclusively related to your trip.
-Access to your tour leaders through emails or calls
-Guests who wish to arrive a day or two early can stay at the same hotel where the tour begins, eliminating the need to change rooms when the tour starts-we can book it for you
+ So much more
This is a private custom trip lead by two tourleaders for 26 years leading tours.
All that is listed in the itinerary above is included.
-Private drivers
-Private Archaeological guides for multiple sites
-Skip-the-line tickets
-Dinners together where indicated, with wonderful food choices and red or white wines included
-Cooking lesson
-Breakfast in each hotel (full)
-Flight (with 50 lb luggage accepted)
-Ferries
-Winery
-Enjoying the activities with your private group
-Pre-tour Zoom meetings
-Your own Passport Page, along with eight supporting documents, all exclusively related to your trip.
-Access to your tour leaders through emails or calls
-Guests who wish to arrive a day or two early can stay at the same hotel where the tour begins, eliminating the need to change rooms when the tour starts-we can book it for you
+ So much more
Trip Cost
for 12 people and up 10,900 per person double occupancy
for 10 people and up 11,400 per person double occupancy
for 8 people and up 11,900 per person double occupancy
If you are traveling solo please add $1500 to the above total
for 12 people and up 10,900 per person double occupancy
for 10 people and up 11,400 per person double occupancy
for 8 people and up 11,900 per person double occupancy
If you are traveling solo please add $1500 to the above total
Trip Terms
This trip is limited to 14 people (not including the two tour leaders) and will run with 8 people.
A deposit of $1500 per person is needed to secure this trip. The deposit is due by August 15 2026 in order to secure your trip. The deposit is fully refundable at any time until the final payment is received. The final payment of $9400 (12 people and up), $9900 (10 people and up), and $10,400 (8 people and up)
per person is due by June 15 2027. After the final payment is received your trip is no longer refundable.
This trip is limited to 14 people (not including the two tour leaders) and will run with 8 people.
A deposit of $1500 per person is needed to secure this trip. The deposit is due by August 15 2026 in order to secure your trip. The deposit is fully refundable at any time until the final payment is received. The final payment of $9400 (12 people and up), $9900 (10 people and up), and $10,400 (8 people and up)
per person is due by June 15 2027. After the final payment is received your trip is no longer refundable.
What is not included
Flights: Airfare from the US to Greece and back
Meals: Any meals not specified in the itinerary.
Hotel Taxes: Tourist, environmental, or room taxes (€8–€12 per room, per night), payable at check-out.
Optional Activities: Transportation to and from activities not listed in the main itinerary.
Health & Medical Needs: Any required medications, medical expenses, or personal health-related costs.
Travel Insurance: Strongly recommended. If declined, a waiver must be signed.
Personal Expenses: Any costs for individual needs, including medications, vaccinations, and other health-related requirements.
Travel Documents: Passports, visas, or any other necessary documentation.
Communication Costs: Mobile phone, internet, or other communication expenses.
Flights: Airfare from the US to Greece and back
Meals: Any meals not specified in the itinerary.
Hotel Taxes: Tourist, environmental, or room taxes (€8–€12 per room, per night), payable at check-out.
Optional Activities: Transportation to and from activities not listed in the main itinerary.
Health & Medical Needs: Any required medications, medical expenses, or personal health-related costs.
Travel Insurance: Strongly recommended. If declined, a waiver must be signed.
Personal Expenses: Any costs for individual needs, including medications, vaccinations, and other health-related requirements.
Travel Documents: Passports, visas, or any other necessary documentation.
Communication Costs: Mobile phone, internet, or other communication expenses.
Thinking about extending your time in Greece?
Why not join us for our Crete AddOn+
This features the Venetian port of Heraklion, Knossos and the Heraklion Archaeological Museum, traditional cretan tavernas, olive oil and wine tasting,
Why not join us for our Crete AddOn+
This features the Venetian port of Heraklion, Knossos and the Heraklion Archaeological Museum, traditional cretan tavernas, olive oil and wine tasting,
Day One AddOn+
October 11 2027
Heraklion
The Island of Crete
Today we’ll journey from the Cyclades to Crete, Greece’s largest and most storied island. Our private driver will meet us at our hotel on Santorini and transfer us comfortably to the port, where we’ll board a fast ferry bound for Heraklion (2 hours). We’ll enjoy the scenic crossing as the deep blue Aegean gives way to Crete’s historic northern coast.
Upon arrival in Heraklion, our private driver will be waiting to escort us to our luxury boutique accommodations, ideally situated right on the coast. Perfectly positioned for exploration on foot, our hotel places us within easy reach of Heraklion’s vibrant streets, historic landmarks, and seaside promenades.
As the afternoon softens into evening, we will lead you on a gentle introduction walk through Heraklion Old Town, where ancient walls, lively squares, and local cafés reveal the city’s character. We’ll continue toward the Venetian Port of Heraklion, where the sea breeze, stone fortifications, and glowing sunset set the tone for our first night on Crete.
Dinner this evening is reserved at a traditional Cretan taverna, where we’ll be introduced to the island’s celebrated cuisine—fresh ingredients, local olive oil, and time-honored recipes served with warm hospitality.
Includes:
October 11 2027
Heraklion
The Island of Crete
Today we’ll journey from the Cyclades to Crete, Greece’s largest and most storied island. Our private driver will meet us at our hotel on Santorini and transfer us comfortably to the port, where we’ll board a fast ferry bound for Heraklion (2 hours). We’ll enjoy the scenic crossing as the deep blue Aegean gives way to Crete’s historic northern coast.
Upon arrival in Heraklion, our private driver will be waiting to escort us to our luxury boutique accommodations, ideally situated right on the coast. Perfectly positioned for exploration on foot, our hotel places us within easy reach of Heraklion’s vibrant streets, historic landmarks, and seaside promenades.
As the afternoon softens into evening, we will lead you on a gentle introduction walk through Heraklion Old Town, where ancient walls, lively squares, and local cafés reveal the city’s character. We’ll continue toward the Venetian Port of Heraklion, where the sea breeze, stone fortifications, and glowing sunset set the tone for our first night on Crete.
Dinner this evening is reserved at a traditional Cretan taverna, where we’ll be introduced to the island’s celebrated cuisine—fresh ingredients, local olive oil, and time-honored recipes served with warm hospitality.
Includes:
- Full breakfast
- Private driver transfer from our hotel in Santorini to the port
- Fast ferry tickets from Santorini to Heraklion, Crete
- Private driver pickup from the port of Heraklion to our hotel
- Hotel near the sea with sea views and a rooftop pool
- Dinner together
- Our own personalized Passport Page
- Overnight in Heraklion, Crete
This is an example of the style and standard of accommodation you may expect in Heraklion Crete.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Day Two AddOn+
October 12 2027
Crete: Palace of Knossos & Treasures of the Minoans
After breakfast, we’ll pack our bags and leave them for our private driver to pick up as we make our way to the Heraklion Archaeological Museum, where skip-the-line tickets ensure a smooth and effortless entry. This museum is considered one of the most important in Greece—housing an extraordinary collection of Minoan artifacts uncovered primarily at nearby Knossos and other archaeological sites across Crete. As we explore, we’ll take our time discovering intricately detailed frescoes, ceremonial objects, jewelry, pottery, and everyday items that reveal the sophistication of Europe’s earliest advanced civilization. These remarkable treasures bring the ancient Minoans vividly to life and provide essential context for understanding Crete’s pivotal role in Mediterranean history.
We will break for a light lunch (we'll have recommendations for good places nearby) before being picked up by our driver and taken to the legendary Palace of Knossos, one of the most important archaeological sites in Greece and the heart of the ancient Minoan Civilization. With our skip-the-line tickets, we’ll explore this remarkable palace complex with an expert private guide who will bring its history to life. We’ll learn about the myths of King Minos and the Minotaur, admire the restored frescoes, and walk through the grand courtyards, royal apartments, and ceremonial spaces that date back over 4,000 years. Knossos offers a fascinating glimpse into Europe’s earliest advanced society.
Later in the afternoon we are headed for Rethymnon, with its Venetian Harbor and wonderful old town.
For the evening, we’re happy to recommend several tavernas in town for authentic Cretan cuisine paired with exceptional local ingredients in an atmosphere that reflects the island’s warm hospitality.
Includes:
October 12 2027
Crete: Palace of Knossos & Treasures of the Minoans
After breakfast, we’ll pack our bags and leave them for our private driver to pick up as we make our way to the Heraklion Archaeological Museum, where skip-the-line tickets ensure a smooth and effortless entry. This museum is considered one of the most important in Greece—housing an extraordinary collection of Minoan artifacts uncovered primarily at nearby Knossos and other archaeological sites across Crete. As we explore, we’ll take our time discovering intricately detailed frescoes, ceremonial objects, jewelry, pottery, and everyday items that reveal the sophistication of Europe’s earliest advanced civilization. These remarkable treasures bring the ancient Minoans vividly to life and provide essential context for understanding Crete’s pivotal role in Mediterranean history.
We will break for a light lunch (we'll have recommendations for good places nearby) before being picked up by our driver and taken to the legendary Palace of Knossos, one of the most important archaeological sites in Greece and the heart of the ancient Minoan Civilization. With our skip-the-line tickets, we’ll explore this remarkable palace complex with an expert private guide who will bring its history to life. We’ll learn about the myths of King Minos and the Minotaur, admire the restored frescoes, and walk through the grand courtyards, royal apartments, and ceremonial spaces that date back over 4,000 years. Knossos offers a fascinating glimpse into Europe’s earliest advanced society.
Later in the afternoon we are headed for Rethymnon, with its Venetian Harbor and wonderful old town.
For the evening, we’re happy to recommend several tavernas in town for authentic Cretan cuisine paired with exceptional local ingredients in an atmosphere that reflects the island’s warm hospitality.
Includes:
- Full breakfast
- Skip-the-line entrance tickets to the Heraklion Archaeological Museum
- Private driver to the Palace of Knossos
- Private guided tour of Knossos
- Skip-the-line entrance tickets for Knossos
- Private driver to from the Palace of Knossos to Rethymnon
- Dinner recommendations and reservations
- Our own personalized Passport Page
- Overnight in Rethymnon Crete
Day Three AddOn+
October 13 2027
This morning is yours to fully embrace the charm of Rethymnon at your own pace. Lose yourself in the winding lanes of the Old Town, where bougainvillea spills from balconies, hidden courtyards invite quiet moments, and every corner reveals a glimpse of Crete’s Venetian and Ottoman past.
Wander up to the Fortezza for panoramic views over the sea and harbor, browse the boutiques and artisan shops tucked into the backstreets, or simply enjoy a leisurely coffee while soaking in the atmosphere. The beauty of the town is yours to discover.
In the afternoon, join us as we journey into the Cretan countryside for a memorable wine and olive oil tasting experience. Crete is celebrated for its award-winning wines, and you’ll have the opportunity to sample a variety of exceptional local vintages while learning about the island’s ancient winemaking traditions. We’ll also savor some of Crete’s finest extra virgin olive oils — dipping fresh bread, tasting the rich flavors, and discovering why Cretan olive oil is considered among the best in the world.
This evening, we’ll gather together for dinner at a beloved local taverna known for its authentic Cretan specialties.
Includes:
October 13 2027
This morning is yours to fully embrace the charm of Rethymnon at your own pace. Lose yourself in the winding lanes of the Old Town, where bougainvillea spills from balconies, hidden courtyards invite quiet moments, and every corner reveals a glimpse of Crete’s Venetian and Ottoman past.
Wander up to the Fortezza for panoramic views over the sea and harbor, browse the boutiques and artisan shops tucked into the backstreets, or simply enjoy a leisurely coffee while soaking in the atmosphere. The beauty of the town is yours to discover.
In the afternoon, join us as we journey into the Cretan countryside for a memorable wine and olive oil tasting experience. Crete is celebrated for its award-winning wines, and you’ll have the opportunity to sample a variety of exceptional local vintages while learning about the island’s ancient winemaking traditions. We’ll also savor some of Crete’s finest extra virgin olive oils — dipping fresh bread, tasting the rich flavors, and discovering why Cretan olive oil is considered among the best in the world.
This evening, we’ll gather together for dinner at a beloved local taverna known for its authentic Cretan specialties.
Includes:
- Full breakfast
- Curated self-guided exploration of Rethymnon’s Old Town
- Time to visit the Fortezza and wander the charming backstreets at your leisure
- Afternoon excursion into the Cretan countryside with private driver
- Guided wine tasting featuring award-winning local Cretan wines
- Olive oil tasting with fresh local bread and regional specialties
- Insights into Crete’s winemaking and olive oil traditions
- Dinner at a beloved local taverna featuring authentic Cretan cuisine
- Overnight Rethymnon-Venetian Harbor and old town
Day Four AddOn+
October 14 2027
Today is yours to enjoy exactly as you choose — a chance to slow down, explore, and experience Crete at your own pace. Whether you’re seeking relaxation, adventure, history, or simply a beautiful day soaking in the island’s atmosphere, the possibilities are endless.
Perhaps you’ll spend the day at one of Rethymno's nearby beaches, where crystal-clear waters invite you for a refreshing swim or a peaceful stroll along the shoreline. Settle into a seaside taverna for a leisurely lunch, feel the sea breeze, and embrace the laid-back rhythm of island life.
For those drawn to history and culture, consider a visit to the remarkable Arkadi Monastery, one of Crete’s most treasured landmarks and a UNESCO-recognized historic site. Dating back to the 14th century, the monastery is both breathtaking and deeply significant to Cretan history, offering beautiful architecture, peaceful courtyards, and panoramic countryside views.
If nature calls, the lush beauty of Mili Gorge offers a completely different side of the island. This scenic 4-kilometer walking trail winds through olive groves, citrus trees, and shaded pathways, passing the remains of more than 30 historic mills that once powered the area’s flour production — the inspiration behind the gorge’s name. It’s a peaceful and immersive way to experience Crete’s natural beauty and rural heritage.
Or perhaps today simply becomes your day to linger in a café, browse local boutiques, sip wine overlooking the sea, or unwind by the pool with nowhere to be and no schedule to follow.
Whatever you choose, we are here to help arrange transportation, recommendations, and/ or reservations to make the day effortless and memorable. Today is about freedom, discovery, and enjoying Crete exactly the way you wish.
Includes:
October 14 2027
Today is yours to enjoy exactly as you choose — a chance to slow down, explore, and experience Crete at your own pace. Whether you’re seeking relaxation, adventure, history, or simply a beautiful day soaking in the island’s atmosphere, the possibilities are endless.
Perhaps you’ll spend the day at one of Rethymno's nearby beaches, where crystal-clear waters invite you for a refreshing swim or a peaceful stroll along the shoreline. Settle into a seaside taverna for a leisurely lunch, feel the sea breeze, and embrace the laid-back rhythm of island life.
For those drawn to history and culture, consider a visit to the remarkable Arkadi Monastery, one of Crete’s most treasured landmarks and a UNESCO-recognized historic site. Dating back to the 14th century, the monastery is both breathtaking and deeply significant to Cretan history, offering beautiful architecture, peaceful courtyards, and panoramic countryside views.
If nature calls, the lush beauty of Mili Gorge offers a completely different side of the island. This scenic 4-kilometer walking trail winds through olive groves, citrus trees, and shaded pathways, passing the remains of more than 30 historic mills that once powered the area’s flour production — the inspiration behind the gorge’s name. It’s a peaceful and immersive way to experience Crete’s natural beauty and rural heritage.
Or perhaps today simply becomes your day to linger in a café, browse local boutiques, sip wine overlooking the sea, or unwind by the pool with nowhere to be and no schedule to follow.
Whatever you choose, we are here to help arrange transportation, recommendations, and/ or reservations to make the day effortless and memorable. Today is about freedom, discovery, and enjoying Crete exactly the way you wish.
Includes:
- Personalized assistance arranging activities and experiences in and around Rethymnon
- Recommendations for exploring the charming Old Town, hidden alleyways, cafés, and scenic harbor areas
- Time to browse the boutiques and artisan shops along Souliou Street, one of the town’s most beloved shopping streets
- Opportunity to visit the historic Neratze Mosque, known for its elegant Venetian and Ottoman architectural influences
- Visit to the Archaeological Museum of Rethymno to discover artifacts and stories from Crete’s rich ancient past
- Free time to enjoy Crete’s beautiful coastline, including options such as:
- Preveli Beach — famous for its dramatic palm forest, river lagoon, and crystal-clear waters
- Rethymno Beach — a stunning 13-kilometer stretch of golden sand perfect for swimming, walking, or relaxing by the sea
- Optional visit to the historic Arkadi Monastery, one of Crete’s most important cultural and historical landmarks
- Opportunity to hike through the lush landscapes of Mili Gorge, passing olive groves, citrus trees, and the remains of historic water mills
- Overnight Rethymnon-Venetian Harbor and old town
This is an example of the style and standard of accommodation you may expect in Rethymnon Crete.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Day Five AddOn+
October 15 2027
After breakfast and one last stroll through the winding lanes and Venetian harbor of Rethymnon, we depart with our private driver for the scenic journey west to Chania — one of the most beautiful drives on the island. Rather than heading directly there, we will take our time along the northern coast of Crete, stopping at hidden villages, monasteries, dramatic viewpoints, and seaside tavernas that capture the spirit of the island.
Along the way, we'll stop at:
Arriving in Chania in the afternoon, we will check into our hotel in the middle of the old town right near the harbor and later a local guide will lead us on a walking tour through the enchanting old town and harbor of Chania, where Venetian, Ottoman, and Greek influences blend together in one of the Mediterranean’s most atmospheric cities.
Highlights of our tour include:
October 15 2027
After breakfast and one last stroll through the winding lanes and Venetian harbor of Rethymnon, we depart with our private driver for the scenic journey west to Chania — one of the most beautiful drives on the island. Rather than heading directly there, we will take our time along the northern coast of Crete, stopping at hidden villages, monasteries, dramatic viewpoints, and seaside tavernas that capture the spirit of the island.
Along the way, we'll stop at:
- Georgioupoli — a charming seaside village perfect for coffee by the beach or a short walk to the tiny white chapel sitting out in the sea.
- Vamos — a traditional village in the Apokoronas region where time seems to slow down among stone houses and olive groves.
- Scenic coastal viewpoints overlooking Souda Bay, with opportunities to stop for photographs of the White Mountains and the sparkling Cretan Sea.
Arriving in Chania in the afternoon, we will check into our hotel in the middle of the old town right near the harbor and later a local guide will lead us on a walking tour through the enchanting old town and harbor of Chania, where Venetian, Ottoman, and Greek influences blend together in one of the Mediterranean’s most atmospheric cities.
Highlights of our tour include:
- Firkas Fortress — the historic Venetian fortress guarding the entrance to the harbor.
- Skridlof Street — better known as “Knife Street,” where skilled Cretan craftsmen continue the centuries-old tradition of handmade knives.
- Municipal Market of Chania (if it is still open, if not we will catch it tomorrow) — the vibrant agora filled with local cheeses, herbs, olive oils, honey, spices, and regional delicacies.
- Old Venetian Harbor of Chania — the stunning 14th-century harbor lined with Venetian buildings, waterfront cafés, fishing boats, and the iconic lighthouse.
- This evening, join us for dinner at a traditional harbor taverna where we will enjoy authentic Cretan cuisine, local wines, warm hospitality, and the magical atmosphere of Chania by night.
- Breakfast
- Private driver transfer from Rethymnon to Chania with scenic and cultural highlight stops along the way
- Lunch on your own in one of the charming villages or seaside towns visited during the journey
- Guided walking tour of Chania with a knowledgeable local guide
- Overnight accommodations at the lux boutique hotel near the Venetian Harbor
- Group dinner at a traditional local taverna with wine included — just like all of our dinners together
- Overnight in Chania
Day Six AddOn+
October 16 2027
Chania
Today you will have two wonderful ways to experience the beauty, culture, and flavors of Crete — whether you prefer an unforgettable outdoor adventure or a relaxed and authentic culinary experience.
Option 1 -
Guided Hike Through Samaria Gorge
For the adventurous traveler, today offers the opportunity to explore the legendary Samaria Gorge, considered the jewel of Crete’s White Mountains and one of the most spectacular hikes in Europe.
Hidden deep within the rugged landscape of southern Crete, the gorge stretches for nearly 18 kilometers through dramatic cliffs, ancient forests, and narrow passages — including the famous “Iron Gates,” where the canyon walls soar high above while narrowing to just a few meters wide. Along the trail you may encounter wild mountain goats known as kri-kri, tiny abandoned villages, fragrant pine forests, and breathtaking mountain scenery throughout the day.
The Samaria Gorge National Park was recognized by UNESCO in 1981 as part of the World Network of Biosphere Reserves for its extraordinary natural beauty and ecological importance.
This fully guided excursion begins early in the morning, departing around 6:10 a.m., and is approximately a 12-hour experience including transportation and the hike itself. The trek is challenging but incredibly rewarding and is best suited for active travelers comfortable walking on uneven terrain for several hours.
Note from The Olive Odysseys-We will have an local outfitter supply us with this activity for those who want it- and the cost is on you-estimated price is 60-80 euros, we will know when we get closer to the trip. Keep in mind this is a 12 hours commitment. You are picked up and taken by bus to start the gorge hike. It is an 18 km (11 mile) walk and even though is it downhill for most of the way, it is a hike with uneven footing in parts. Then you will take a ferry back to Chania. Right now (June 2026) the gorge is temporarily closed due to rock slides.
Option 2 -
Authentic Cretan Cooking Experience & Farewell Dinner.
For those who would prefer a slower and more intimate experience, we will spend the afternoon with a local Cretan family at their beautiful countryside garden restaurant outside Chania.
Surrounded by olive trees, herbs, flowers, and vineyards, our hosts will welcome us into their kitchen and share some of their favorite traditional Cretan recipes passed down through generations. Together we will prepare a variety of authentic dishes using fresh local ingredients — learning the stories, techniques, and traditions behind the island’s celebrated cuisine.
After cooking together, we will sit down for a relaxed farewell dinner featuring many of the dishes we helped create, accompanied by generous samplings of exceptional local Cretan wines. It is a wonderful opportunity to celebrate our farewell dinner together while enjoying warm hospitality, delicious food, laughter, and the flavors that make Crete so unforgettable.
Includes
October 16 2027
Chania
Today you will have two wonderful ways to experience the beauty, culture, and flavors of Crete — whether you prefer an unforgettable outdoor adventure or a relaxed and authentic culinary experience.
Option 1 -
Guided Hike Through Samaria Gorge
For the adventurous traveler, today offers the opportunity to explore the legendary Samaria Gorge, considered the jewel of Crete’s White Mountains and one of the most spectacular hikes in Europe.
Hidden deep within the rugged landscape of southern Crete, the gorge stretches for nearly 18 kilometers through dramatic cliffs, ancient forests, and narrow passages — including the famous “Iron Gates,” where the canyon walls soar high above while narrowing to just a few meters wide. Along the trail you may encounter wild mountain goats known as kri-kri, tiny abandoned villages, fragrant pine forests, and breathtaking mountain scenery throughout the day.
The Samaria Gorge National Park was recognized by UNESCO in 1981 as part of the World Network of Biosphere Reserves for its extraordinary natural beauty and ecological importance.
This fully guided excursion begins early in the morning, departing around 6:10 a.m., and is approximately a 12-hour experience including transportation and the hike itself. The trek is challenging but incredibly rewarding and is best suited for active travelers comfortable walking on uneven terrain for several hours.
Note from The Olive Odysseys-We will have an local outfitter supply us with this activity for those who want it- and the cost is on you-estimated price is 60-80 euros, we will know when we get closer to the trip. Keep in mind this is a 12 hours commitment. You are picked up and taken by bus to start the gorge hike. It is an 18 km (11 mile) walk and even though is it downhill for most of the way, it is a hike with uneven footing in parts. Then you will take a ferry back to Chania. Right now (June 2026) the gorge is temporarily closed due to rock slides.
Option 2 -
Authentic Cretan Cooking Experience & Farewell Dinner.
For those who would prefer a slower and more intimate experience, we will spend the afternoon with a local Cretan family at their beautiful countryside garden restaurant outside Chania.
Surrounded by olive trees, herbs, flowers, and vineyards, our hosts will welcome us into their kitchen and share some of their favorite traditional Cretan recipes passed down through generations. Together we will prepare a variety of authentic dishes using fresh local ingredients — learning the stories, techniques, and traditions behind the island’s celebrated cuisine.
After cooking together, we will sit down for a relaxed farewell dinner featuring many of the dishes we helped create, accompanied by generous samplings of exceptional local Cretan wines. It is a wonderful opportunity to celebrate our farewell dinner together while enjoying warm hospitality, delicious food, laughter, and the flavors that make Crete so unforgettable.
Includes
- Breakfast
- Option 1 as listed above-Samaria Gorge Hike (please choose one option-in this case dinner will be on your own), the cost is on you-estimated price is 60-80 euros, we will know when we get closer to the trip.
- Option 2 as listed above-Afternoon cooking class segueing into dinner (please choose one option) This option is included in the cost of your trip.
- Overnight accommodations at the lux boutique hotel in Chania
- Overnight in Chania
This is an example of the style and standard of accommodation you may expect in Chania Crete.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Please note that no specific hotel can be guaranteed until your booking is confirmed.
Day Seven AddOn+
October 17 2027
Return to the US. We will be on hand to help you get to the airport for your return flight to the US
We bid you Kalo Taxidi, which means have a good trip in Greece.
Includes
Breakfast
October 17 2027
Return to the US. We will be on hand to help you get to the airport for your return flight to the US
We bid you Kalo Taxidi, which means have a good trip in Greece.
Includes
Breakfast
What is included-
All of the hotels, activities, transportation, meals etc,
as detailed above
Plus two tour leaders and private guides and drivers where indicated.
All of the hotels, activities, transportation, meals etc,
as detailed above
Plus two tour leaders and private guides and drivers where indicated.
Trip Cost AddOn+
Per person double occupancy
$6990
If you are traveling solo please add $900 to the above total
Per person double occupancy
$6990
If you are traveling solo please add $900 to the above total
Trip Terms
A deposit of $1000 per person is needed to secure this AddOn+ The deposit is due by August 15 2026 in order to secure your trip. The deposit is fully refundable at any time until the final payment is received. The final payment of $. per person is due by June 15 2027. After the final payment is received your trip on the AddOn+ is no longer refundable.
What is not included
Flights: Airfare from the US to Greece and back
Meals: Any meals not specified in the itinerary.
Hotel Taxes: Tourist, environmental, or room taxes (€8–€12 per room, per night), payable at check-out.
Optional Activities: Transportation to and from activities not listed in the main itinerary.
Health & Medical Needs: Any required medications, medical expenses, or personal health-related costs.
Travel Insurance: Strongly recommended. If declined, a waiver must be signed.
Personal Expenses: Any costs for individual needs, including medications, vaccinations, and other health-related requirements.
Travel Documents: Passports, visas, or any other necessary documentation.
Communication Costs: Mobile phone, internet, or other communication expenses.
Flights: Airfare from the US to Greece and back
Meals: Any meals not specified in the itinerary.
Hotel Taxes: Tourist, environmental, or room taxes (€8–€12 per room, per night), payable at check-out.
Optional Activities: Transportation to and from activities not listed in the main itinerary.
Health & Medical Needs: Any required medications, medical expenses, or personal health-related costs.
Travel Insurance: Strongly recommended. If declined, a waiver must be signed.
Personal Expenses: Any costs for individual needs, including medications, vaccinations, and other health-related requirements.
Travel Documents: Passports, visas, or any other necessary documentation.
Communication Costs: Mobile phone, internet, or other communication expenses.
