Adventure and Romance Tour of Italy & Greece

Colorful town of Varenna on Lake Como, Italy

What to expect on this itinerary

Lose yourself in luxury, history and romance as you effortlessly drift through Italy and Greece on this three-week tour. Beginning in the Venetian canals, we lead you through the hearts of opulence in Lake Como and the Italian Riviera before you find yourself at peace on the whitewashed island of Santorini in the Aegean Sea. Complemented by authentic Tuscan feasts and quiet seaside Italian towns, this three-week tour will reveal all that is magical, timeless and positively cherished in these two quintessential European countries.

Countries Visited

Greece, Italy

Places Visited

Venice, Lake Como, Bellagio, Portofino, Italian Riviera, Cinque Terre, Tuscany, Florence, Santorini, Oia

Suggested Duration

22 Days

Customizable Itinerary

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Day 1

Venice - Romance Beings in the Canals of Venice

Touching down in Venice, not a moment of romance or adventure is wasted. Upon arrival, you will connect with a water taxi that will transfer you through these infamous canals, arriving eventually at your hotel. Perched on the edge of the Riva delgi Schiavoni – mere steps away from St Mark’s Square and the Doge Palace, the white Istria stone façade of the hotel shimmers in the lagoon below. The hotel has retained the original Biedermeier furnishings inside, which creates an elegant and relaxed atmosphere that feels almost untouched by time. As you enter your unique suite, you will catch your first soaring view of this effervescent city, building excitement for all that lies ahead.

What's Included:

Transfer
Accommodation
Day 2

Venice - Exploring a Rare and Authentic Venice

Day 3

Venice - The Art and Antiquity of the Islands in the Venice Lagoon

Day 4

Lake Como - Travel by Train to the Opulent Shores of Lake Como

Day 5

Lake Como - Weaving and Wandering Bellagio

Day 6

Lake Como - Acquaint Yourself with the Romance of Lake Como

Day 7

Portofino - Travel by Ferry and Train to Your Villa in Portofino

Day 8

Portofino - Explorations of Portofino’s Landscape, Culture and Indulgences

Day 9

Portofino - Trave to Cinque Terre to Explore Seaside Terraced Villages

Day 10

Florence - Disappear into the Heart of Tuscany

Day 11

Florence - Feel the Inspirational Power of Val d’Orcia

Day 12

Florence - Explore the Heart of the Renaissance

Day 13 - 15

Florence - Sink into the Rhythm of Florence

Day 16

Santorini - Travel via Rome to Greece

Day 17

Santorini - Casual Explorations of Santorini

Day 18

Santorini - The Beaches of the Aegean Cyclades

Day 19

Santorini - Dipping Below the Surface of the Aegean Sea

Day 20

A Lighthouse and Sunset in Akrotiri Caldera Beach

Day 21

Santorini - A Final Blissful Day in Greece

Day 22

Santorini - Return Home

Trip Highlights

  • Glide through the Venetian canals on a gondola, admiring the impossible romance of this ancient city
  • Sail across Lake Como to the pinnacle of luxury, finding your rhythm in the lakeside town of Bellagio
  • Find yourself between sea and olive tree as you wander between the five colorful and historic towns of Cinque Terre
  • Lose yourself in the heart of the Renaissance, wandering and feasting your way across the rolling hills of Tuscany
  • Find total relaxation in the Agean Sea, spending six blissful days between whitewashed buildings and delicately powerful views
  • Indulge in every Italian and Grecian delicacy conceivable, as you move effortlessly between wine lands, olive fields, ocean and village 

Detailed Description

Blissful, passionate, and utterly comprehensive, this three-week itinerary shares with you every ounce of romance, opulence and adventure that Italy and Greece have to offer. From the canals of Venice through to the shores of Santorini, and every vineyard, restaurant, gallery and alleyway that lies between, you will not only visit – but also experience – the most coveted sights in the region. Traveling between luxury accommodation by rail, ferry and plane, there are few opportunities more decadent than this.

Beginning in Venice, Italy first captures your imagination with her Venetian masks, island-based glass blowers and delicate lace shops. After strolling the alleyways and drifting on gondolas, you then move onto the utterly exclusive shores of Lake Como and the Italian Riviera, where luxury and charm intersect beneath the mountains. From there, you travel through the ever-charming villages of Cinque Terre, moving on to the rolling hills of Tuscany. Vineyards, the Renaissance and a stream of Tuscan flavors will characterize your remaining days in Italy, before you eventually travel onwards to Greece by way of Rome.

Your adventure concludes with a full week on the whitewashed island of Santorini. Adored for her simple elegance and timeless character, a visit here requires little more than drifting between sunsets with ouzo in hand. Days are filled just as much as you desire – with many opting to slip into lagoons, wander beneath windmills and savor the fresh flavors emerging out of taverns. Innumerable beaches, each more unique and stunning than the next, are sure to entice you in the late afternoon. Here, you can wait for sunset to turn a whitewashed lighthouse a dusty shade of pink, before you reviews eventually return back to reality – just a little more enchanted. 

For more itinerary options, browse the Italy tours and Greece tours on Zicasso.

Starting Price

$9,400 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

4.9

Verified Traveler Reviews

Based on 836 reviews

Italy Mother-Daughter Vacation Review: Lake Como, Florence, Rome, Cinque Terre, Winery Tour, 12 Nights

My daughter and I had an absolutely incredible experience with Zicasso's travel agency. Everything was perfect and customized to our preferences. Communication was professional, responsive, and reassuring. Every detail of our trip was handled with such great care, from personalized tours in Lake Como, Florence, and Rome to hotel selections in Como and Cinque Terre. Working with the agency was personal and seamless. Their careful and personal attention made our mother-daughter Italian adventure completely stress-free. I would definitely recommend them when planning a trip to Italy. Grazie mille!

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Italy Honeymoon Review: Rome, Sorrento, Florence, Venice, Vineyard, Wine Experience, 11-Night Trip

Zicasso's tour company did a wonderful job of planning our dream honeymoon! Our travel agent took into consideration our wants and wishes, and created half- and full-day activities for us throughout the trip. We were able to visit four locations (Rome, Sorrento, Florence, and Venice) while in Italy. The trip was a perfect mix of relaxation and exploration. The tour company took away the stress of traveling and allowed us to enjoy the days without worries.

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Italy Travel Review: Local Culture, Cuisine, 3 Weeks
"Zicasso’s travel company did a great job organizing our trip. The pacing was just perfect between guided activities and time to explore on our own."

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Italy Trip Review: Rome, Venice, Florence, the Amalfi Coast, Lake Como, 12 Nights

The Zicasso travel team did an outstanding job in organizing our trip to Italy, including stays in Rome, Venice, Florence, the Amalfi Coast, and Lake Como. The hotels, private car and boat tours, and guides were excellent. Everything went very smoothly and was first rate. Everyone was on time, polite, and knowledgeable. It was a pleasure working with the team to finalize the itinerary and the trip was all-encompassing. Definitely five stars!

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Italy Tour Review: Venice, Tuscany, Rome, Amalfi Coast, Capri, Cooking Class, Ferrari Experience, 2-Week Vacation

We had the best time during our wonder trip to Italy. We explored Venice, Tuscany, Rome, and the Amalfi Coast. Zicasso's travel agency arranged the most beautiful hotels, with exceptional service, and fun and exciting tours in each location.

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Italy Family Vacation Review: Lake Como, Tuscany, Private Driver, Sant'Agnese, Villages, Local Cuisine, Private Tour, 9-Night Trip

From start to finish, Zicasso's travel agents handled our trip beautifully.

The highlights were the private boat trip on Lake Como, as our captain and guide was excellent. The private drive through Tuscany, seeing small villages. The lunch and wine tour at Sant'Agnese was wonderful; the chicken recipe superb. The vinegars and oils of 10 to 30 years in the making, along with the wine, were excellent.

Both agents were always there for us along our trip, which made it so nice to know how responsive they always were. Our family trip to Italy was all we hoped for and more. We thank the agency so much for helping us make family memories in beautiful Italy.

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

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