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Italy & Greece

Italy & Greece

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Starting from: $4690 / per person

Experience the magnificent highlights of Italy and Greece on this trip, delving deep into culture and history without sacrificing time to relax by the water.

Colosseum, Roman Forum & Vatican

Boat trip from Positano to Capri with stop for Blue Grotto

Tuscany day trip including home-cooked meal at a winery

Gondola ride through the canals of Venice

Sailing tour around the island of Santorini


Luxury hotels within 5 minutes’ walk of historic center

Buffet breakfast each day

Private transfers from beginning to end

Reserved seating on luxury trains

Knowledgable, enthusiastic guides

Skip the line tickets

Tour Plan


Day 1: Departure

Depart the United States on an overnight flight bound for Rome, Italy.

Day 2: Arrival

Benvenuto in Italia! Land in Rome, Italy’s capital city and hotbed of history, where you will be met and transferred to your hotel. Rest up on the rooftop terrace or in the library lounge before taking your free afternoon to visit the nearby Campo de’ Fiori or Piazza Navona.

Day 3: Vatican

Without ever breaking Rome’s outer borders you will visit the smallest country in the world: Vatican City. Peruse the art of the Vatican Museums, marvel at St. Peter’s Basilica, and gaze at the ceiling of the Sistine Chapel, accompanied by the knowledge your private tour guide shares with you. After some downtime in the afternoon, set off on a food tour and indulge in everything from pasta to gelato to porchetta.

Day 4: Ancient Rome

Spend the morning traveling back in time on a private tour through the Colosseum and Roman Forum, learning all the ins and outs of these longstanding structures. Take the afternoon to yourself to wander Rome, where you are sure to stumble across more massive monuments such as the Spanish Steps or Trevi Fountain.

Day 5: Travel to Positano

Unwind and enjoy your luxury train ride en route to the seaside gem of the Amalfi Coast, Positano. After checking into your hotel, spend the afternoon lounging with a view of the sea and glass of wine in hand from the comfort of your own balcony.

Day 6: Capri Boat Tour

Set sail for Capri, where you will be given several hours to wander the island at your own pace. You will also have the chance to enjoy the sea to its fullest, passing wondrous rock formations and stopping for an opportunity to swim in the crystal blue water. If the tide cooperates, you may even have the chance to take a trip through the iconic Blue Grotto.

Day 7: Leisure Day

Today, you may choose not to stray too far and relax by the beach or venture off to nearby towns. In the morning, you could take a short ferry ride to the region’s namesake, Amalfi, to admire the medieval architecture. From there, you could take a taxi up the craggy cliffside to Ravello, an ideal spot to settle down at a lovely restaurant for dinner and watch the sun set over the water.

Day 8: Travel to Florence

Journey from Positano to Florence onboard your luxury train, complete with refreshments and an entertainment system. Take in the Duomo from your window, or make the short walk from your hotel to view it up close. This evening, attend a cooking class where you will learn how to make a few different pasta doughs and sauces. The best part: diving into the fruits of your labor afterwards.

Day 9: Chianti

For the day, you will have a private driver at your disposal to take you to one of the most renowned wine regions of Italy, Chianti. Wind your way through the rolling landscape of Tuscany to quaint hilltop towns with no shortage of wine bars, cafes, and craft shops. Stop at a winery to taste wine, aged balsamic vinegar, and olive oil. Visit the cellars, and sit down for a home-cooked lunch overlooking the vineyards.

Day 10: Travel to Venice

Depart Florence and watch the Italian countryside roll by from the window of your luxury train. Arrive in Venice, the wondrous city built on more than 100 islands in a lagoon in the Adriatic sea. Indulge in afternoon tea at your hotel, where a small array of pastries and fruit juices will also be available, before embarking on your private gondola ride through the canals of the city.

Day 11: Leisure Day

Today, you may choose to hop on a ferry and branch out to a couple of other Venetian islands. Burano and Murano are both lively, colorful islands home to incredible artisan work. Find worldrenowned, handmade lace in Burano and masterworks of glass in Murano.

Day 12: Travel to Santorini

Wave goodbye to Italy from your flight bound for Santorini, the iconic island of Greece easily recognized by its bright white buildings and blue dome roofs. Your morning may be busy, but by the afternoon you will be lounging by your hotel’s pool with a cocktail bar mere steps away.

Day 13: Catamaran

Take to the seas on a catamaran to experience some of the best Santorini has to offer, passing everything from the Red and White Beaches to the ancient city of Akrotiri to volcanic island of Aspronisi. Stops will be made at hot springs and secluded bays where you can wade your way into the alluring waters.

Day 14: Leisure Day

After spending a day at sea, you may wish to spend today traversing the island by foot. Make your way from Imerovigli to Oia with stunning views of the sea and caldera guiding you along. Reward yourself with a sunset dinner at one of the fish tavernas in the tiny hardor town of Ammoudi, located below the cliffs where Oia is perched.

Day 15: Travel to Naxos

Skip across the water on your ferry from Santorini to Naxos, the largest island in the Cyclades. Spend the afternoon sprawled across a lounge chair on your hotel’s private beach.

Day 16: Leisure Day

While having a private beach at your hotel is nice, you may choose to go and see the other sandy oases Naxos has to offer. The beaches of Agia Anna and Agios Prokopios are some of the most beloved in Europe for their natural beauty. If you are looking for a little more adventure by go surfing or jet skiing, head to Plaka where a variety of water sports activities are readily available.

Day 17: Travel to Athens

Soar over the Aegean on your flight from Naxos to Athens, the heart of what was once Ancient Greece. Gaze upon the center of it all, The Acropolis, from the rooftop of your hotel over a snack or cocktails.

Day 18: Leisure Day

Now is your chance to experience the Acropolis up close. Wind your way up the marble ruins to the most exemplary of them all: the Parthenon. These monuments have survived have from wars to earthquakes, changing hands of ownership from civilization to civilization over time. Today, the Acropolis is fiercely protected by law and hailed as one of the most popular UNSECO World Heritage sites.

Day 19: Departure

Say farewell to Greece as you head to the airport for your flight back to the United States.

Tour Location

Experience the magnificent highlights of Italy and Greece on this trip, delving deep into culture and history without sacrificing time to relax by the water.


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