• Welcome to The Olive Odysseys
  • Call us at 1-440-804-5062
  • Contact Us
  • Luxury Guided Small-Group Tours
  • Customized Private Tours
  • Personalized Trip Planning
  • Privacy Policy
1-440-804-5062
  • Welcome to The Olive Odysseys
  • Call us at 1-440-804-5062
  • Contact Us
  • Luxury Guided Small-Group Tours
  • Customized Private Tours
  • Personalized Trip Planning
  • Privacy Policy
Picture
Picture

Laura Adams Family in Greece September 2026
Greek Isles Getaway
Together in Greece

What You Shared With Us:
  • A late September trip to the Greek Isles with your family
  • 6 adults and one 13-month-old traveling together
  • A strong love for the beach and ocean
  • Interest in cooking class and hands-on culinary experience
  • Desire to explore olive oil tastings and local wineries
  • A focus on enjoying great food throughout the trip
  • Interest in boating and time on the water
  • Appreciation for culture and history, in balanced, relaxed doses
  • A preference high-quality accommodations in great areas where access is easy for each person
  • A setup with shared common spaces (kitchen, living areas), while each sub-group has their own private bedroom and bathroom

Itinerary 1

Day One – Arrival in Athens
Arrive in Athens, where a private driver will meet you at the airport and transfer you to your centrally located accommodation—ideally near the Acropolis in one of the city’s most charming pedestrian areas.
Enjoy a relaxed afternoon exploring the vibrant neighborhood beneath the Acropolis, filled with cafés, boutique shops, and inviting restaurants. We’re happy to provide restaurant recommendations and secure reservations if desired. If time allows, consider a brief visit to the spectacular Acropolis Museum for an inspiring introduction to your journey. 
Overnight in Athens

Day Two – Acropolis & Island of Paros
Begin your day with an early morning private guided tour of the Acropolis, complete with skip-the-line access. Our expert guides bring to life the history and significance of this iconic site—the birthplace of democracy and a cornerstone of Western civilization.
In the afternoon, transfer to the port for a high-speed ferry to the island of Paros. Upon arrival, a private driver will take you to one of our favorite areas of the island—a picturesque seaside town that retains its authentic fishing village charm while offering exceptional shops, restaurants, and beaches.
Overnight on Paros

Day Three – Paros at Leisure
Enjoy a full day to explore Paros at your own pace. We can arrange a customized day of sightseeing and beach hopping, along with visits to local olive oil producers and wineries.
In the evening, unwind with a seaside aperitif before dinner at one of the island’s many outstanding restaurants, known for fresh seafood and relaxed outdoor dining.
Overnight on Paros

Day Four – Sailing or Island Exploration
Today offers several wonderful options. Weather permitting, we can arrange a private or semi-private catamaran cruise, taking you to secluded beaches where you can swim in crystal-clear waters while enjoying food and drinks onboard.
Alternatively, consider a day trip to a nearby island. We’ll guide you to a lesser-known destination where you can experience an exceptional beach and a traditional taverna—an authentic and memorable Greek experience few travelers discover.
In addition, Paros offers a great cooking class that we love. We can get you in so that you can learn Greek spcaitalites that are easy to make at home.
Overnight on Paros

Day Five – Paros to Naxos
This morning, take a short ferry ride to the island of Naxos. Less dependent on tourism and deeply rooted in agriculture, Naxos offers one of the most authentic experiences in the Greek Isles. As always, private drivers will ensure seamless transfers between ports and accommodations.
In the evening, enjoy a scenic walk to the Temple of Apollo (Portara), a stunning spot for sunset. Naxos is renowned for its cuisine, and we’ll recommend a selection of traditional tavernas showcasing the island’s rich culinary heritage.
Overnight on Naxos

Day Six – Discovering Naxos
Today, a private driver can take you around the island to explore its highlights. Visit local producers to sample citron liqueur (unique to Naxos), along with exceptional wines and olive oils.
Return to your accommodations in the afternoon for some time to relax at the beach. In the evening, we’ll suggest another memorable dining experience.
Overnight on Naxos

Day Seven – Leisure & Adventure
Enjoy a flexible day with options to suit your mood. Choose between a relaxing beach day or another boating experience—catamarans and private boats are readily available.
Naxos is home to a variety of beautiful beaches, easily accessible by car or jeep. We’re happy to arrange transportation based on your preferences, ensuring a smooth and enjoyable final day on the island.
Overnight on Naxos
​

Departure
The following day, we recommend flying back to Athens from Naxos. Several reliable Greek airlines operate this route, with a quick and convenient flight time of approximately 50 minutes.

Itinerary 2

​Similar to the above, with one key adjustment: we’ve included two dedicated days on the island of your choice—either Santorini or Milos, depending on your preference.

Day One – Arrival in Athens
Arrive in Athens, where a private driver will meet you at the airport and transfer you to your centrally located accommodation—ideally near the Acropolis in one of the city’s most charming pedestrian areas.
Enjoy a relaxed afternoon exploring the vibrant neighborhood beneath the Acropolis, filled with cafés, boutique shops, and inviting restaurants. We’re happy to provide restaurant recommendations and secure reservations if desired. If time allows, consider a brief visit to the spectacular Acropolis Museum for an inspiring introduction to your journey. 
Overnight in Athens

Day Two – Acropolis & Island of Paros
Begin your day with an early morning private guided tour of the Acropolis, complete with skip-the-line access. Our expert guides bring to life the history and significance of this iconic site—the birthplace of democracy and a cornerstone of Western civilization.
In the afternoon, transfer to the port for a high-speed ferry to the island of Paros. Upon arrival, a private driver will take you to one of our favorite areas of the island—a picturesque seaside town that retains its authentic fishing village charm while offering exceptional shops, restaurants, and beaches.
Overnight on Paros

Day Three – Paros at Leisure
Enjoy a full day to explore Paros at your own pace. We can arrange a customized day of sightseeing and beach hopping, along with visits to local olive oil producers and wineries.
In the evening, unwind with a seaside aperitif before dinner at one of the island’s many outstanding restaurants, known for fresh seafood and relaxed outdoor dining.
Overnight on Paros

Day Four – Sailing or Island Exploration
Today offers several wonderful options. Weather permitting, we can arrange a private or semi-private catamaran cruise, taking you to secluded beaches where you can swim in crystal-clear waters while enjoying food and drinks onboard.
Alternatively, consider a day trip to a nearby island. We’ll guide you to a lesser-known destination where you can experience an exceptional beach and a traditional taverna—an authentic and memorable Greek experience few travelers discover.
In addition, Paros offers a great cooking class that we love. We can get you in so that you can learn Greek spcaitalites that are easy to make at home.
Overnight on Paros

Day Five – Paros to Naxos
This morning, take a short ferry ride to the island of Naxos. Less dependent on tourism and deeply rooted in agriculture, Naxos offers one of the most authentic experiences in the Greek Isles. As always, private drivers will ensure seamless transfers between ports and accommodations.
In the evening, enjoy a scenic walk to the Temple of Apollo (Portara), a stunning spot for sunset. Naxos is renowned for its cuisine, and we’ll recommend a selection of traditional tavernas showcasing the island’s rich culinary heritage.
Overnight on Naxos

Day Six – Discovering Naxos
Today, a private driver can take you around the island to explore its highlights. Visit local producers to sample citron liqueur (unique to Naxos), along with exceptional wines and olive oils.
Return to your accommodations in the afternoon for some time to relax at the beach. In the evening, we’ll suggest another memorable dining experience.
Overnight on Naxos

Day Seven – Leisure & Adventure
Enjoy a flexible day with options to suit your mood. Choose between a relaxing beach day or another boating experience—catamarans and private boats are readily available.
Naxos is home to a variety of beautiful beaches, easily accessible by car or jeep. We’re happy to arrange transportation based on your preferences, ensuring a smooth and enjoyable final day on the island.
Overnight on Naxos

Day Eight – Arrival in Santorini
Today, you’ll travel by high-speed ferry to the iconic island of Santorini. Private drivers will ensure seamless transfers both upon departure from Naxos and upon arrival in Santorini.
Once you arrive, you’ll be escorted to the stunning village of Oia, known for its whitewashed architecture and breathtaking caldera views. We have several exceptional accommodation options to recommend, each offering the iconic vistas Santorini is famous for.
Settle in and enjoy time at leisure—perhaps relaxing poolside while taking in the dramatic scenery. In the evening, we’re happy to recommend and reserve some of the island’s most sought-after bars and restaurants, where you can fully experience the unique atmosphere and beauty of Santorini.
Overnight in Santorini

Day Nine – Santorini at Your Pace
Today is yours to design. You may wish to explore Santorini’s renowned vineyards with a curated tasting experience, offering insight into the island’s distinctive wines.
Alternatively, consider a catamaran cruise around the caldera, with stops at the volcanic hot springs and opportunities to swim in the Aegean’s crystal-clear waters.
Whether you prefer relaxation or exploration, we will tailor the day to match your interests, creating a memorable and effortless experience.
Overnight in Santorini

Alternative Option – Milos
As an alternative to Santorini or one of the other islands, you may consider including the island of Milos—known for its unique landscapes and stunning beaches. We would review ferry schedules and logistics to seamlessly incorporate it into your itinerary.

Departure
On your final day, we recommend a short flight from Santorini back to Athens. Several reliable Greek airlines operate this route, with a flight time of approximately 50 minutes, ensuring a smooth and convenient conclusion to your journey.

Please keep in mind that the above is just a rough sketch.
​In order to fill out your trip and go to pricing you would need to decide your final itinerary. 
We can change around anything you want. It is your trip after all!
As seen on-
Picture
Click here to read these articles

See our privacy policy here

Contact

The Olive Odysseys 
46 Shopping Plaza
​Drive # 107
Chagrin Falls, Ohio
​44022 U.S.A
Phone: ​1-440-804-5062
​
[email protected]
Copyright 2025-2026 All Right Reserved
Picture
A member of the
​American Society of Travel Advisors
  • Welcome to The Olive Odysseys
  • Call us at 1-440-804-5062
  • Contact Us
  • Luxury Guided Small-Group Tours
  • Customized Private Tours
  • Personalized Trip Planning
  • Privacy Policy