This 'bucket list' trip has it all- from stunning Lake Como in the north to the Amalfi Coast in the south!
Your Dates Here
Lake Como, Villas, Insider Venice, Rural Tuscan Farms, David in Florence, Pompeii, Fast Trains, Private Transportation, Skip-the-line Tickets + So Much More.
Day One – Lake Como
Welcome to the stunning Lake Como, a jewel of northern Italy framed by soaring mountains and shimmering waters. Upon arrival at your boutique hotel, you’ll be greeted with a glass of local wine—a perfect toast to the beginning of your Italian adventure.
After settling in, embark on a leisurely orientation walk through the charming town of Varenna, with its narrow cobbled streets, colorful houses, and picturesque waterfront promenade. Your stroll will include a visit to the Villa Monastero, a historic villa whose botanical gardens are home to thousands of rare and exotic plant species. Wander through terraces overflowing with vibrant flowers, century-old trees, and fragrant herbs, while enjoying breathtaking views over the glimmering lake. Along the way, your hosts at The Olive Odysseys will share insider tips on other must-see sights in and around Varenna.
As evening approaches, you’ll have the opportunity to dine at one of Varenna’s charming local restaurants, where traditional Italian cuisine is elevated with fresh, seasonal ingredients. Your hosts can assist with personalized dinner recommendations and reservations, ensuring your first night on Lake Como is as magical as the scenery itself.
Includes:
Welcome to the stunning Lake Como, a jewel of northern Italy framed by soaring mountains and shimmering waters. Upon arrival at your boutique hotel, you’ll be greeted with a glass of local wine—a perfect toast to the beginning of your Italian adventure.
After settling in, embark on a leisurely orientation walk through the charming town of Varenna, with its narrow cobbled streets, colorful houses, and picturesque waterfront promenade. Your stroll will include a visit to the Villa Monastero, a historic villa whose botanical gardens are home to thousands of rare and exotic plant species. Wander through terraces overflowing with vibrant flowers, century-old trees, and fragrant herbs, while enjoying breathtaking views over the glimmering lake. Along the way, your hosts at The Olive Odysseys will share insider tips on other must-see sights in and around Varenna.
As evening approaches, you’ll have the opportunity to dine at one of Varenna’s charming local restaurants, where traditional Italian cuisine is elevated with fresh, seasonal ingredients. Your hosts can assist with personalized dinner recommendations and reservations, ensuring your first night on Lake Como is as magical as the scenery itself.
Includes:
- Welcome glass of local wine
- Self-guided tour of the Villa Monastero botanical gardens and the town of Varenna (includes entrance tickets)
- Dinner recommendations and reservations
- Boutique hotels right in the action
- 24/7 contact with The Olive Odysseys during your tour
- Overnight stay in Lake Como – Varenna
"Best vacation EVER!"
Jim and Linda H.
Akron, Ohio
Jim and Linda H.
Akron, Ohio
Day Two – Lake Como
Start your morning early as you embark on a journey across Lake Como, one of Italy’s most glamorous and scenic destinations. Your first stop is the charming town of Lenno, home to the exquisite Villa del Balbianello, built in 1787 and famed for its elegant architecture and cinematic gardens. With your private guided tour, you’ll explore the villa’s richly decorated rooms, imagining the lives of the aristocratic families who once called it home. Step outside into the terraced gardens, where perfectly manicured lawns, fragrant flowers, and cypress trees seem to float above the sparkling lake—an idyllic setting that has captivated visitors and filmmakers alike.
Next, you’ll continue your journey on the water to the enchanting town of Bellagio, often called the “Pearl of Lake Como.” Stroll along its cobbled streets lined with boutiques, artisan shops, and vibrant cafés. Pause for lunch at one of the charming cafés overlooking the lake, where you can savor fresh, local specialties while watching the gentle waves lap the shore. Afterward, wander at your leisure, taking in the town’s elegant villas, colorful gardens, and breathtaking panoramic views.
In the afternoon, you’ll return by ferry to Varenna, a picturesque village perched on the eastern shore of the lake. Here, the narrow streets, quaint piazzas, and waterfront promenades invite a relaxed exploration. Your hosts at The Olive Odysseys will provide recommendations for dinner, whether you prefer a cozy trattoria serving homemade pasta or a romantic waterfront restaurant.
Includes:
Start your morning early as you embark on a journey across Lake Como, one of Italy’s most glamorous and scenic destinations. Your first stop is the charming town of Lenno, home to the exquisite Villa del Balbianello, built in 1787 and famed for its elegant architecture and cinematic gardens. With your private guided tour, you’ll explore the villa’s richly decorated rooms, imagining the lives of the aristocratic families who once called it home. Step outside into the terraced gardens, where perfectly manicured lawns, fragrant flowers, and cypress trees seem to float above the sparkling lake—an idyllic setting that has captivated visitors and filmmakers alike.
Next, you’ll continue your journey on the water to the enchanting town of Bellagio, often called the “Pearl of Lake Como.” Stroll along its cobbled streets lined with boutiques, artisan shops, and vibrant cafés. Pause for lunch at one of the charming cafés overlooking the lake, where you can savor fresh, local specialties while watching the gentle waves lap the shore. Afterward, wander at your leisure, taking in the town’s elegant villas, colorful gardens, and breathtaking panoramic views.
In the afternoon, you’ll return by ferry to Varenna, a picturesque village perched on the eastern shore of the lake. Here, the narrow streets, quaint piazzas, and waterfront promenades invite a relaxed exploration. Your hosts at The Olive Odysseys will provide recommendations for dinner, whether you prefer a cozy trattoria serving homemade pasta or a romantic waterfront restaurant.
Includes:
- Breakfast
- Ferry to Lenno and Villa del Balbianello
- Private guided tour of Villa del Balbianello
- Ferry to the town of Bellagio
- Time to explore and have lunch in Bellagio
- Ferry back to Varenna
- Boutique hotels right in the action
- 24/7 contact with The Olive Odysseys during your tour
- Overnight stay in Lake Como – Varenna
Day Three – Venice
Your day begins with a private driver who will escort you comfortably back to Milan, where you’ll board Italy’s sleek high-speed train bound for Venice—the city of shimmering canals, graceful gondolas, and timeless romance.
Upon arrival, you’ll settle into your boutique hotel, perfectly situated amid Venice’s enchanting labyrinth of alleys and canals—close to all the action, yet steeped in the city’s old-world charm. After check-in, set out for a leisurely introductory stroll through the magical heart of Venice. Cross arched stone bridges, wander along the Grand Canal, and lose yourself in the quiet beauty of hidden courtyards and sunlit squares. With your curated walking route in hand, you’ll discover secret corners and local gems that most visitors miss.
As evening falls, your hotel will welcome you with a chilled glass of Prosecco, Italy’s beloved sparkling wine—born right here in the Veneto region. Toast to your arrival in one of the most interesting cities on Earth.
When it’s time for dinner, you’ll find yourself spoiled for choice. From intimate candlelit trattorias tucked along narrow lanes to lively restaurants overlooking the water, Venice’s culinary scene is a feast for the senses. Your hosts at The Olive Odysseys will provide handpicked recommendations and happily secure reservations at your restaurant of choice. Perhaps tonight you’ll try a creamy risotto al nero di seppia (squid ink risotto) or freshly grilled branzino, paired perfectly with a crisp local white wine.
After dinner, take an evening walk through softly lit piazzas, the sound of distant music echoing across the canals. Venice by night feels like stepping into a painting—quiet, mysterious, and utterly captivating.
Includes:
Your day begins with a private driver who will escort you comfortably back to Milan, where you’ll board Italy’s sleek high-speed train bound for Venice—the city of shimmering canals, graceful gondolas, and timeless romance.
Upon arrival, you’ll settle into your boutique hotel, perfectly situated amid Venice’s enchanting labyrinth of alleys and canals—close to all the action, yet steeped in the city’s old-world charm. After check-in, set out for a leisurely introductory stroll through the magical heart of Venice. Cross arched stone bridges, wander along the Grand Canal, and lose yourself in the quiet beauty of hidden courtyards and sunlit squares. With your curated walking route in hand, you’ll discover secret corners and local gems that most visitors miss.
As evening falls, your hotel will welcome you with a chilled glass of Prosecco, Italy’s beloved sparkling wine—born right here in the Veneto region. Toast to your arrival in one of the most interesting cities on Earth.
When it’s time for dinner, you’ll find yourself spoiled for choice. From intimate candlelit trattorias tucked along narrow lanes to lively restaurants overlooking the water, Venice’s culinary scene is a feast for the senses. Your hosts at The Olive Odysseys will provide handpicked recommendations and happily secure reservations at your restaurant of choice. Perhaps tonight you’ll try a creamy risotto al nero di seppia (squid ink risotto) or freshly grilled branzino, paired perfectly with a crisp local white wine.
After dinner, take an evening walk through softly lit piazzas, the sound of distant music echoing across the canals. Venice by night feels like stepping into a painting—quiet, mysterious, and utterly captivating.
Includes:
- Breakfast
- Private transport to Milan train station
- Fast train to Venice
- Introductory stroll of Venice-self guided
- Welcome glass of Prosecco
- Dinner recommendations and reservations
- UNESCO World Heritage Site: Venice & The Lagoon
- Boutique hotels right in the action
- 24/7 contact with The Olive Odysseys during your tour
- Overnight stay in Venice
Day Four – Venice
This morning, you’ll set out on your own 'vaporetto cruise' up the Grand Canal, Venice’s “main street,” where elegant palaces and churches rise directly from the water, their reflections shimmering like living art.
Your private guide will meet you for an in-depth exploration of historic Venice, beginning with the breathtaking Basilica di San Marco. With your skip-the-line access, you’ll step inside this 11th-century masterpiece, where every surface glows with glittering Byzantine mosaics and marble inlay. Climb to the basilica’s balcony for an up-close look at the famed bronze horses, said to have been taken from the Hippodrome of Constantinople and brought to Venice as symbols of triumph. From this vantage point, you’ll enjoy an unforgettable view over Piazza San Marco and the domes of the lagoon beyond.
Next, you’ll continue through Venice’s labyrinth of narrow streets and graceful bridges to the Rialto Bridge, one of the city’s oldest and most beloved landmarks. From here, take in the bustling life of the Grand Canal—merchant boats, gondolas, and vaporetti drifting past centuries-old façades. Your guide will lead you to the Rialto Market, a lively and colorful spot where Venetians have shopped for fresh fish and produce for nearly a thousand years.
When your guided tour concludes, you’ll find yourself near several inviting options for lunch. Perhaps a trattoria serving silky squid ink pasta, or a hidden bacaro offering cicchetti—Venetian-style tapas—with a glass of crisp Prosecco.
The afternoon is yours to embrace Venice at your own pace. Linger at a sidewalk café and watch the world drift by, or perhaps take a romantic gondola ride through quiet back canals where the only sounds are the water and your gondolier’s song. If you wish to explore further, your guide can help you reach the charming islands of Murano and Burano, known for their centuries-old traditions of glassblowing and lace-making.
Dinner is on your own this evening, with personalized recommendations from The Olive Odysseys to suit your tastes—from cozy candlelit osterie to elegant lagoon-view restaurants.
Includes:
This morning, you’ll set out on your own 'vaporetto cruise' up the Grand Canal, Venice’s “main street,” where elegant palaces and churches rise directly from the water, their reflections shimmering like living art.
Your private guide will meet you for an in-depth exploration of historic Venice, beginning with the breathtaking Basilica di San Marco. With your skip-the-line access, you’ll step inside this 11th-century masterpiece, where every surface glows with glittering Byzantine mosaics and marble inlay. Climb to the basilica’s balcony for an up-close look at the famed bronze horses, said to have been taken from the Hippodrome of Constantinople and brought to Venice as symbols of triumph. From this vantage point, you’ll enjoy an unforgettable view over Piazza San Marco and the domes of the lagoon beyond.
Next, you’ll continue through Venice’s labyrinth of narrow streets and graceful bridges to the Rialto Bridge, one of the city’s oldest and most beloved landmarks. From here, take in the bustling life of the Grand Canal—merchant boats, gondolas, and vaporetti drifting past centuries-old façades. Your guide will lead you to the Rialto Market, a lively and colorful spot where Venetians have shopped for fresh fish and produce for nearly a thousand years.
When your guided tour concludes, you’ll find yourself near several inviting options for lunch. Perhaps a trattoria serving silky squid ink pasta, or a hidden bacaro offering cicchetti—Venetian-style tapas—with a glass of crisp Prosecco.
The afternoon is yours to embrace Venice at your own pace. Linger at a sidewalk café and watch the world drift by, or perhaps take a romantic gondola ride through quiet back canals where the only sounds are the water and your gondolier’s song. If you wish to explore further, your guide can help you reach the charming islands of Murano and Burano, known for their centuries-old traditions of glassblowing and lace-making.
Dinner is on your own this evening, with personalized recommendations from The Olive Odysseys to suit your tastes—from cozy candlelit osterie to elegant lagoon-view restaurants.
Includes:
- Breakfast
- Vaporetto 'cruise' and view of the Grand Canal of Venice
- Private guided tour of St. Mark’s Basilica and Venice’s historic neighborhoods
- Skip-the-line entry to Basilica di San Marco
- Visit to the Rialto Bridge and Market
- Lunch recommendations
- UNESCO World Heritage Site: Venice & The Lagoon
- Boutique hotels right in the action
- 24/7 contact with The Olive Odysseys during your tour
- Overnight stay in Venice
"A tour with Patricia & Manolis is the only way to go
if you want your trip to be experience of a lifetime."
Laura A. Davis, Bentleyville, OH
if you want your trip to be experience of a lifetime."
Laura A. Davis, Bentleyville, OH
Day Five – Florence
Early morning in Venice is pure magic—the canals shimmer in the soft light, gondolas glide quietly past, and the city feels as if it belongs entirely to you. Enjoy one last stroll through the winding alleyways or along the Grand Canal before or after breakfast—it’s your choice.
By mid-morning, you’ll bid farewell to Venice and board a high-speed train bound for Florence, the cradle of the Renaissance. Sit back and watch the Italian countryside unfold outside your window as you travel swiftly to one of the most culturally rich cities in the world.
Upon arrival, a private driver will be waiting to whisk you directly to your boutique hotel, perfectly situated in the heart of Florence. After check-in, you’ll set out on a delightful orientation walk through the Historic Center, a UNESCO World Heritage Site where every street corner seems to tell a story.
You’ll stroll past the majestic Duomo, with its world-famous dome designed by Brunelleschi—a symbol of Florentine genius and ambition. Nearby, marvel at Giotto’s Campanile and the ornate Baptistry, whose bronze doors Michelangelo once called “the Gates of Paradise.” Continue your walk through elegant piazzas filled with sculpture and history, and pause at Piazza della Signoria to admire the outdoor replica of Michelangelo’s David, standing proudly where the original once did.
Florence is also a shopper’s paradise. You’ll have time to browse the city’s legendary leather markets, where artisans craft handbags, belts, and jackets using centuries-old traditions.
When evening falls, the city glows with romance. We will provide hand-picked trattoria recommendations and make dinner reservations for you—perhaps tonight is the perfect time to try the famous Florentine steak, grilled to perfection and served with a robust Tuscan red.
Includes:
You'll pass by the Duomo and the Campiello and take our time visiting the piazzas and the outdoor David. There will be time for shopping at some of the best leather markets in Italy.
There are several very good trattorias that we can recommend and if you are up to it you can try the famous Florentine steak!
Includes- Breakfast/ Fast train to Florence/ Self guided orientation Walk of Florence/ Dinner recommendations and reservations/ UNESCO World Heritage Site (Historic Center of Florence)/ Overnight Florence.
Early morning in Venice is pure magic—the canals shimmer in the soft light, gondolas glide quietly past, and the city feels as if it belongs entirely to you. Enjoy one last stroll through the winding alleyways or along the Grand Canal before or after breakfast—it’s your choice.
By mid-morning, you’ll bid farewell to Venice and board a high-speed train bound for Florence, the cradle of the Renaissance. Sit back and watch the Italian countryside unfold outside your window as you travel swiftly to one of the most culturally rich cities in the world.
Upon arrival, a private driver will be waiting to whisk you directly to your boutique hotel, perfectly situated in the heart of Florence. After check-in, you’ll set out on a delightful orientation walk through the Historic Center, a UNESCO World Heritage Site where every street corner seems to tell a story.
You’ll stroll past the majestic Duomo, with its world-famous dome designed by Brunelleschi—a symbol of Florentine genius and ambition. Nearby, marvel at Giotto’s Campanile and the ornate Baptistry, whose bronze doors Michelangelo once called “the Gates of Paradise.” Continue your walk through elegant piazzas filled with sculpture and history, and pause at Piazza della Signoria to admire the outdoor replica of Michelangelo’s David, standing proudly where the original once did.
Florence is also a shopper’s paradise. You’ll have time to browse the city’s legendary leather markets, where artisans craft handbags, belts, and jackets using centuries-old traditions.
When evening falls, the city glows with romance. We will provide hand-picked trattoria recommendations and make dinner reservations for you—perhaps tonight is the perfect time to try the famous Florentine steak, grilled to perfection and served with a robust Tuscan red.
Includes:
- Breakfast
- Fast train to Florence
- Private driver from the train station to your hotel
- Self-guided orientation walk of Florence
- Dinner recommendations and reservations
- UNESCO World Heritage Site: Historic Center of Florence
- Boutique hotels right in the action
- 24/7 contact with The Olive Odysseys during your tour
- Overnight stay in Florence
You'll pass by the Duomo and the Campiello and take our time visiting the piazzas and the outdoor David. There will be time for shopping at some of the best leather markets in Italy.
There are several very good trattorias that we can recommend and if you are up to it you can try the famous Florentine steak!
Includes- Breakfast/ Fast train to Florence/ Self guided orientation Walk of Florence/ Dinner recommendations and reservations/ UNESCO World Heritage Site (Historic Center of Florence)/ Overnight Florence.
Day Six – Florence
Awaken early for an unforgettable day in the heart of the Renaissance. You’ll begin your morning with a visit to the Galleria dell’Accademia with skip-the-line tickets, home to one of the most iconic masterpieces in the world--Michelangelo’s David. Standing beneath this breathtaking sculpture, you’ll feel the genius and passion of the Renaissance era all around you.
Next, you’ll make your way to the magnificent Duomo of Florence, officially known as the Cathedral of Santa Maria del Fiore. Its extraordinary dome, engineered by Brunelleschi, remains one of the greatest architectural feats in history. Take your time to wander through the sanctuary, admire the golden mosaics of the Baptistry, or climb to the top of the Campanile for sweeping views of the city’s terracotta rooftops and the Tuscan hills beyond. For your visit to the Campanile and the Baptistry we will have skip-the-line tickets for you.
Lunch will be your choice of a sunlit piazza with a glass of Chianti and a plate of fresh pasta—or try a local trattoria tucked down one of Florence’s cobblestone lanes. We will point out some of our favorites.
In the afternoon, you’ll stroll through the historic heart of the city, a UNESCO World Heritage Site, passing by the world-renowned Uffizi Gallery, crossing the Ponte Vecchio with its glittering goldsmith shops, and finishing at the Palazzo Pitti, the grand former residence of the powerful Medici family. The rest of the day is yours to explore Florence’s elegant streets, artisan boutiques, and open-air cafes. Your hosts at The Olive Odysseys will be available to share their favorite insider recommendations.
Includes:
Awaken early for an unforgettable day in the heart of the Renaissance. You’ll begin your morning with a visit to the Galleria dell’Accademia with skip-the-line tickets, home to one of the most iconic masterpieces in the world--Michelangelo’s David. Standing beneath this breathtaking sculpture, you’ll feel the genius and passion of the Renaissance era all around you.
Next, you’ll make your way to the magnificent Duomo of Florence, officially known as the Cathedral of Santa Maria del Fiore. Its extraordinary dome, engineered by Brunelleschi, remains one of the greatest architectural feats in history. Take your time to wander through the sanctuary, admire the golden mosaics of the Baptistry, or climb to the top of the Campanile for sweeping views of the city’s terracotta rooftops and the Tuscan hills beyond. For your visit to the Campanile and the Baptistry we will have skip-the-line tickets for you.
Lunch will be your choice of a sunlit piazza with a glass of Chianti and a plate of fresh pasta—or try a local trattoria tucked down one of Florence’s cobblestone lanes. We will point out some of our favorites.
In the afternoon, you’ll stroll through the historic heart of the city, a UNESCO World Heritage Site, passing by the world-renowned Uffizi Gallery, crossing the Ponte Vecchio with its glittering goldsmith shops, and finishing at the Palazzo Pitti, the grand former residence of the powerful Medici family. The rest of the day is yours to explore Florence’s elegant streets, artisan boutiques, and open-air cafes. Your hosts at The Olive Odysseys will be available to share their favorite insider recommendations.
Includes:
- Breakfast
- Visit to the Galleria dell’Accademia (featuring Michelangelo’s David-with skip-the-line tickets)
- Self- guided tour of Florence’s historic landmarks
- The Duomo, Campanile & Baptistry (skip-the-line tickets)
- UNESCO World Heritage Site: Historic Center of Florence
- Boutique hotels right in the action
- 24/7 contact with The Olive Odysseys during your tour
- Overnight stay in Florence
"Our trip with Olive Odysseys was the trip of a lifetime.
All better that we had imagined!"
Brenda G. and Harry L.
U.S.A.
All better that we had imagined!"
Brenda G. and Harry L.
U.S.A.
Day Seven – Tuscany
Today, you’ll leave the bustling streets of Florence behind and journey into the rolling hills of rural Tuscany, winding through the famed Chianti wine region. This scenic drive takes you along charming country roads, past vineyards and olive groves that have shaped Tuscan life for centuries.
Your first stop is the picturesque town of Greve in Chianti, a historic market town that has been at the heart of Tuscan trade since the Middle Ages. Here, you can meander through the lively piazza, sampling some of the region’s finest wines, olive oils, and artisanal products. Choose a quaint café for lunch and enjoy local flavors at your own pace.
Next, you’ll glide deeper into the heart of Tuscany to a charming converted farm estate, where history and hospitality blend seamlessly. Your hosts will welcome you warmly and guide you through their winemaking estate, offering a fascinating glimpse into traditional Tuscan viticulture. Savor a private wine tasting, experiencing the rich complexity of local vintages, followed by an authentic dinner at the estate, prepared with fresh, seasonal ingredients.
This day immerses you in the true spirit of Tuscany—its landscapes, flavors, and timeless traditions—while giving you moments of leisure to soak it all in.
Includes:
Today, you’ll leave the bustling streets of Florence behind and journey into the rolling hills of rural Tuscany, winding through the famed Chianti wine region. This scenic drive takes you along charming country roads, past vineyards and olive groves that have shaped Tuscan life for centuries.
Your first stop is the picturesque town of Greve in Chianti, a historic market town that has been at the heart of Tuscan trade since the Middle Ages. Here, you can meander through the lively piazza, sampling some of the region’s finest wines, olive oils, and artisanal products. Choose a quaint café for lunch and enjoy local flavors at your own pace.
Next, you’ll glide deeper into the heart of Tuscany to a charming converted farm estate, where history and hospitality blend seamlessly. Your hosts will welcome you warmly and guide you through their winemaking estate, offering a fascinating glimpse into traditional Tuscan viticulture. Savor a private wine tasting, experiencing the rich complexity of local vintages, followed by an authentic dinner at the estate, prepared with fresh, seasonal ingredients.
This day immerses you in the true spirit of Tuscany—its landscapes, flavors, and timeless traditions—while giving you moments of leisure to soak it all in.
Includes:
- Breakfast
- Visit to the historic town of Greve
- A surprise stop in the Tuscan countryside
- UNESCO World Heritage Site: San Gimignano
- Private wine tasting
- Dinner at a converted farm estate
- Boutique hotels right in the action
- 24/7 contact with The Olive Odysseys during your tour
- Overnight stay near San Gimignano
Day Eight – Tuscany
Enjoy a leisurely breakfast this morning—no rush, no schedule, just the gentle rhythm of Tuscany surrounding you. Later, a private driver will whisk you to the enchanting medieval village of San Gimignano, a town whose skyline of stone towers has earned it the nickname “The Manhattan of the Middle Ages.” Wander its cobblestone streets, admire centuries-old frescoes, and climb the Torre Grossa for panoramic views of the rolling Tuscan countryside, dotted with vineyards, olive groves, and rustic farmhouses.
San Gimignano is also a haven for shopping, offering artisan crafts, local delicacies, and handmade ceramics. Pause at a sunlit sidewalk café to sip a cappuccino while watching daily life unfold in this timeless town. Lunch is on your own, giving you the freedom to explore hidden trattorias or charming piazzas.
Returning to your Tuscan estate, the afternoon is yours to relax by the pool, read a book, or simply soak in the serenity of your surroundings. Later, immerse yourself in an authentic Tuscan cooking class, learning to prepare regional specialties using fresh, local ingredients. At the end of your culinary adventure, sit down to savor the meal you’ve created, perfectly paired with local wines.
This day blends history, culture, and leisure, allowing you to experience Tuscany in both its ancient and modern rhythms.
Includes:
Enjoy a leisurely breakfast this morning—no rush, no schedule, just the gentle rhythm of Tuscany surrounding you. Later, a private driver will whisk you to the enchanting medieval village of San Gimignano, a town whose skyline of stone towers has earned it the nickname “The Manhattan of the Middle Ages.” Wander its cobblestone streets, admire centuries-old frescoes, and climb the Torre Grossa for panoramic views of the rolling Tuscan countryside, dotted with vineyards, olive groves, and rustic farmhouses.
San Gimignano is also a haven for shopping, offering artisan crafts, local delicacies, and handmade ceramics. Pause at a sunlit sidewalk café to sip a cappuccino while watching daily life unfold in this timeless town. Lunch is on your own, giving you the freedom to explore hidden trattorias or charming piazzas.
Returning to your Tuscan estate, the afternoon is yours to relax by the pool, read a book, or simply soak in the serenity of your surroundings. Later, immerse yourself in an authentic Tuscan cooking class, learning to prepare regional specialties using fresh, local ingredients. At the end of your culinary adventure, sit down to savor the meal you’ve created, perfectly paired with local wines.
This day blends history, culture, and leisure, allowing you to experience Tuscany in both its ancient and modern rhythms.
Includes:
- Breakfast
- Private visit to San Gimignano
- Climb the Torre Grossa for stunning views
- UNESCO World Heritage Site: San Gimignano
- Leisure time at the estate swimming pool
- Hands-on Tuscan cooking class
- Dinner together with local wine
- Boutique hotels right in the action
- 24/7 contact with The Olive Odysseys during your tour
- Overnight stay near San Gimignano
"5 Star Tour Guides -
Just the right cadence of activities and free time.
They use boutique hotels and everything is first class.
We will surely travel with them again!"
Barbara and Doug C.
Iowa U.S.A.
Just the right cadence of activities and free time.
They use boutique hotels and everything is first class.
We will surely travel with them again!"
Barbara and Doug C.
Iowa U.S.A.
Day Nine – Sorrento
Today, you’ll bid farewell to Florence and board a high-speed train to Naples, where stunning views of the Tuscan and Campanian countryside will unfold outside your window in complete comfort. Upon arrival, a private driver will be waiting to escort you to one of the world’s most extraordinary archaeological sites: Pompeii. With skip-the-line tickets and a private guide, you’ll wander this vast Roman city frozen in time by the eruption of Mount Vesuvius in 79 AD, exploring ancient villas, frescoed walls, bustling marketplaces, and the amphitheater—all while imagining life in the Roman Empire.
After your Pompeii experience, your driver will transport you further south along the breathtaking Amalfi Coast to Sorrento, perched atop cliffs overlooking the Bay of Naples. From your hotel, you can soak in the sweeping vistas of Vesuvius and the glittering coastline, a view that has inspired artists and poets for centuries.
Sorrento’s heart has been transformed into an exclusive pedestrian zone, perfect for a leisurely evening stroll. Discover charming shops, lively piazzas, and inviting restaurants where you can choose to dine at your leisure.
This day is a seamless blend of history, culture, and scenic luxury—a perfect introduction to southern Italy.
Includes:
Today, you’ll bid farewell to Florence and board a high-speed train to Naples, where stunning views of the Tuscan and Campanian countryside will unfold outside your window in complete comfort. Upon arrival, a private driver will be waiting to escort you to one of the world’s most extraordinary archaeological sites: Pompeii. With skip-the-line tickets and a private guide, you’ll wander this vast Roman city frozen in time by the eruption of Mount Vesuvius in 79 AD, exploring ancient villas, frescoed walls, bustling marketplaces, and the amphitheater—all while imagining life in the Roman Empire.
After your Pompeii experience, your driver will transport you further south along the breathtaking Amalfi Coast to Sorrento, perched atop cliffs overlooking the Bay of Naples. From your hotel, you can soak in the sweeping vistas of Vesuvius and the glittering coastline, a view that has inspired artists and poets for centuries.
Sorrento’s heart has been transformed into an exclusive pedestrian zone, perfect for a leisurely evening stroll. Discover charming shops, lively piazzas, and inviting restaurants where you can choose to dine at your leisure.
This day is a seamless blend of history, culture, and scenic luxury—a perfect introduction to southern Italy.
Includes:
- Breakfast
- Private transport to Florence station
- Fast train to Naples
- Private, skip-the-line tour of Pompeii with expert guide
- Private transport to Sorrento along the Amalfi Coast
- UNESCO World Heritage Site: Amalfi Coast
- Boutique hotels right in the action
- 24/7 contact with The Olive Odysseys during your tour
- Overnight stay in Sorrento
Day Ten – Sorrento & the Amalfi Coast
This morning, you’ll 'set sail' along the stunning Amalfi Coast aboard a ferry, with the sparkling waters of the Tyrrhenian Sea stretching out before you. As you glide past Capri in the distance and the cliffs of the Amalfi coastline up close, you’ll witness one of Italy’s most iconic panoramas--dramatic cliffs dotted with pastel villages, lemon groves, and terraced vineyards, all kissed by the Mediterranean sun.
Upon arriving in Positano, the jewel of the Amalfi Coast, you can linger seaside with a cappuccino, explore the narrow cobblestone streets lined with boutique shops, or browse for exquisite hand-painted ceramics that reflect centuries of local craftsmanship. Of course, the beach beckons for those wanting to soak up the sun and swim in the turquoise waters. This is the perfect day to savor the beauty, elegance, and leisure of the Italian Riviera.
Late in the afternoon, your ferry will return you to Sorrento, giving you one last chance to enjoy the breathtaking coastal scenery from the water.
In the evening, gather for a farewell dinner at a local ristorante, where you’ll toast to your unforgettable journey through Italy—recounting favorite moments.
Includes:
This morning, you’ll 'set sail' along the stunning Amalfi Coast aboard a ferry, with the sparkling waters of the Tyrrhenian Sea stretching out before you. As you glide past Capri in the distance and the cliffs of the Amalfi coastline up close, you’ll witness one of Italy’s most iconic panoramas--dramatic cliffs dotted with pastel villages, lemon groves, and terraced vineyards, all kissed by the Mediterranean sun.
Upon arriving in Positano, the jewel of the Amalfi Coast, you can linger seaside with a cappuccino, explore the narrow cobblestone streets lined with boutique shops, or browse for exquisite hand-painted ceramics that reflect centuries of local craftsmanship. Of course, the beach beckons for those wanting to soak up the sun and swim in the turquoise waters. This is the perfect day to savor the beauty, elegance, and leisure of the Italian Riviera.
Late in the afternoon, your ferry will return you to Sorrento, giving you one last chance to enjoy the breathtaking coastal scenery from the water.
In the evening, gather for a farewell dinner at a local ristorante, where you’ll toast to your unforgettable journey through Italy—recounting favorite moments.
Includes:
- Breakfast
- Ferry to Positano and return
- Time to explore Positano and the Amalfi Coast
- UNESCO World Heritage Site: Amalfi Coast
- Farewell dinner
- Boutique hotels right in the action
- 24/7 contact with The Olive Odysseys during your tour
- Overnight stay in Sorrento
Day Eleven – Farewell from Sorrento
After a final breakfast, it’s time to say goodbye to the magic of Italy. Your unforgettable journey through Florence, Tuscany, and the Amalfi Coast comes to an end this morning in Sorrento, leaving you with memories of stunning landscapes, historic cities, and authentic Italian experiences.
If your schedule allows, you can linger a little longer in Sorrento, enjoying a last stroll through its charming streets, a final espresso in a sun-drenched piazza, or a peaceful moment overlooking the Bay of Naples. Alternatively, you can return to Rome to continue your Italian adventure, exploring its world-famous sites, vibrant neighborhoods, and iconic landmarks.
Either way, your hosts at The Olive Odysseys will be there to ensure your departure is seamless, and to say a heartfelt “arrivederci”” until your next Italian adventure.
Includes:
After a final breakfast, it’s time to say goodbye to the magic of Italy. Your unforgettable journey through Florence, Tuscany, and the Amalfi Coast comes to an end this morning in Sorrento, leaving you with memories of stunning landscapes, historic cities, and authentic Italian experiences.
If your schedule allows, you can linger a little longer in Sorrento, enjoying a last stroll through its charming streets, a final espresso in a sun-drenched piazza, or a peaceful moment overlooking the Bay of Naples. Alternatively, you can return to Rome to continue your Italian adventure, exploring its world-famous sites, vibrant neighborhoods, and iconic landmarks.
Either way, your hosts at The Olive Odysseys will be there to ensure your departure is seamless, and to say a heartfelt “arrivederci”” until your next Italian adventure.
Includes:
- Breakfast
- 24/7 contact with The Olive Odysseys during your tour
Help with your continuation journey or your return to Naples or Rome to fly to the US
What do you get with this tour?
Lake Como
The lake town of Varenna
Villa Monastero and its botanic gardens
The town of Lenno
Visit Villa Balbianello
The Town of Bellagio
Venice
The Grande Canal
Basilica San Marco
Rialto Bridge
Private Guided Tour of Venice
Florence Duomo
Campiello Florence
Galleria dell'Accademia
Walk of Florence
The Chianti Region
Greve in Chianti
The Farm in Tuscany
San Gimignano
The ruins at Pompeii
Sorrento
The Amalfi Coast
Positano
Cooking Lesson
Winery visit
Wine tasting
Prosecco tasting
Fast Trains
Ferry tickets
Skip-The-Line Tickets
Private Transportation
Ten breakfasts
Trip planners with 26 years of experience
Lake Como
The lake town of Varenna
Villa Monastero and its botanic gardens
The town of Lenno
Visit Villa Balbianello
The Town of Bellagio
Venice
The Grande Canal
Basilica San Marco
Rialto Bridge
Private Guided Tour of Venice
Florence Duomo
Campiello Florence
Galleria dell'Accademia
Walk of Florence
The Chianti Region
Greve in Chianti
The Farm in Tuscany
San Gimignano
The ruins at Pompeii
Sorrento
The Amalfi Coast
Positano
Cooking Lesson
Winery visit
Wine tasting
Prosecco tasting
Fast Trains
Ferry tickets
Skip-The-Line Tickets
Private Transportation
Ten breakfasts
Trip planners with 26 years of experience
Price-TBD
Please email us right away to get going on your trip!
This trip can be for 1 to 20 people. Just let us know!
Please email us right away to get going on your trip!
This trip can be for 1 to 20 people. Just let us know!
What is your responsibility?
Airfare to and from Italy*
Transportation to our starting hotel from the airport (we can help with this)
Transportation at the end of the tour
Meals not together as indicated on the itinerary
Transport to and from activities during optional activities
Any medicinal or medical needs while on the trip
Trip insurance should be bought or waiver signed if you choose not to buy it
Expenses arising from personal needs such as medications, vaccinations, travel documents, communications such as mobile phone and internet charges or any other expenses incurred due to traveling.
The Fine Print
Prices are per person which includes all of the above mentioned in the itinerary and is based on double occupancy. Single room rate is $---- per person extra added to the cost of the trip.
Until final payment is paid all deposits are fully refundable. After final payment due date no refunds are available. A payment of final trip payments mean that trip participants
agree to the Trip Terms.
Prices are per person which includes all of the above mentioned in the itinerary and is based on double occupancy. Single room rate is $---- per person extra added to the cost of the trip.
Until final payment is paid all deposits are fully refundable. After final payment due date no refunds are available. A payment of final trip payments mean that trip participants
agree to the Trip Terms.
*Our tour starts in Lake Como and ends in Sorrento.
Your flights can be into Milan and out of Rome or Naples.
We will be on hand to help you book your transatlantic flights to Italy
Your flights can be into Milan and out of Rome or Naples.
We will be on hand to help you book your transatlantic flights to Italy
Who are your leaders?
Manolis & Patricia have had the pleasure of leading trips to Portugal, Spain, France, Italy, Croatia, Greece & Turkey for more than 26 years. They split their time (when they are not on tour) between Ohio and the island of Evia, Greece. In Greece, they live in a rock house off the grid. There they play their guitar (Manolis) and like to sew and garden (Patricia). They adore leading tours and planning tours.
Manolis & Patricia have had the pleasure of leading trips to Portugal, Spain, France, Italy, Croatia, Greece & Turkey for more than 26 years. They split their time (when they are not on tour) between Ohio and the island of Evia, Greece. In Greece, they live in a rock house off the grid. There they play their guitar (Manolis) and like to sew and garden (Patricia). They adore leading tours and planning tours.
