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 4017 reviews

Italy Trip Review: Venice, Como, Tuscany, Florence, Rome, Bellagio, Sistine Chapel, Lake Como Boat Tour
Our custom trip through Italy was one of the most amazing travel experiences we have had. Cameron’s attention to details and knowledge of unique and incredible activities created a whirlwind tour through Venice, Como, Tuscany, Florence, Rome, and more. We had the absolute best hotels, restaurants, tour guides, ground transportation, boat tours, and more. We had the once-in-a-lifetime opportunity to stand in the Sistine Chapel alone, before any other groups, in the cool and quiet of the morning and really take-in the art, history, and feeling of it all. We had a boat tour of Lake Como where we were literally the only ones on the water and with the sunshine peaking through clouds like spotlights on the villas that lined the coast. We had a private lunch of the best northern Italian wines, cheeses, meats, and more while in Bellagio with a charismatic host who told us stories about the vineyards in the region. We had the privilege of having the center table at the fine dining restaurant located in the hills of Tuscany and enjoyed their specially prepared tasting menu. We enjoyed 5-star hotels with rooms that overlooked the Grand Canal in Venice and the Domo in Florence. Our tour guides were traveling professors from prestigious universities, art and architecture historians, and locals who had childhood friendships with museum curators that allowed us special access to restricted areas. If you are thinking about a trip to Italy, I highly recommend you contact Cameron - you will never forget your experience.

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Travel Review: Italy Trip, Venice, Florence, Tuscany, Cinque Terre, Lake Como, 10-Day Tour
We had a wonderful trip visiting Venice, Florence, Tuscany, the Cinque Terre, and Lake Como.  This is the first time we used a travel agency as I generally prefer to make the plans myself.  However, our trip planner did an incredible job and I could not have been happier. I gave her the towns/areas I was thinking about and she came up with a marvelous itinerary--just the right amount of time in each location and tickets/reservations to the important sites to see.  In addition, she arranged all the transfers, hotels, train tickets, and rental cars which made it very easy for us to simply be on vacation.  There is real value to be had by using a knowledgeable, personable, and competent travel advisor, especially when your trip involves several legs, hotels, and modes of transportation.

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Italy Luxury Vacation Review: Milano, Lake Maggiore, Lake Como, Private Tour Guide, Local Culture

Last year we did a fabulous trip to Tuscany. It was our first time traveling with Zicasso and our travel company. It was an incredible and beyond-expectations trip. So this year we decided to repeat the formula and travel to the Lake Region in northern Italy.

We contacted Zicasso and our travel stylist. She knows us well and this time recommended Lago Maggiore, Lago di Como, and Milano, considering every detail - a perfect mix between quiet and astonishingly beautiful towns, active hikes through small towns, and hidden gems hardly seen by tourists. This private journey was perfect, planned as it was to avoid crowds and ensure we could enjoy the beautiful lake region without missing any highlights. We discovered timeless hidden towns and villas, and wonderful people and culture.

We were guided privately every day through different experiences by amazing professionals who gave us a good rundown in history, architecture, and botanical lessons, as well as time to enjoy the beautiful scenery by ourselves.

Our travel agent's recommendations on hotels and restaurants could not have been better.

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Review: Luxury Italy Vacation, Milan, Lake Como, Cinque Terre, Florence, Tuscany

We had a wonderful trip from Lake Como to Milan to Cinque Terre to Florence.  In addition to seeing Florence, Florence was our base for day trips into small beautiful towns in Tuscany. Our agent worked carefully with us from the beginning to get the right mix of independent travel and guided travel during our trip.  It all came together wonderfully during our travels and we have many great memories from this trip as a result.  We strongly recommend this company if you are planning a trip to Italy in the future.  We'll definitely use them again should we decide to revisit this beautiful country.

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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 Tour Review: Rome, Florence, Tuscany, Cinque Terre, Lake Como, Portofino, Private Boat Tour, Cooking Class, Wine Tasting

In general, the trip was fantastic! I worked with a Zicasso tour operator to create a trip and she came through with a terrific itinerary. Our journey to Italy included Rome, Florence, Tuscany, Cinque Terre, and Lake Como. The hotels were well located, although room sizes were small at most of the locations. Travel arrangements between locations were excellent, with drivers on time, vehicles clean, and drivers flexible about intermittent stops. Our planned tours and day trips were well thought out and, with one exception, were some of the trip highlights. The Zicasso staff were available via text and telephone throughout the trip for minor  modifications.

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Customizable Itinerary

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

28,000+ Verified Traveler Reviews