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 1387 reviews

Italy Travel Review: Tuscany, Cinque Terre, Florence, Sunset Cruise, Truffle Hunting, Hiking, Cooking Classes, Olive Oil Mill, Wine Tasting, Museums, 10 Nights

We can't say enough good things about the trip planned for us in Tuscany and Cinque Terre. It was the perfect balance of cultural (museums, artwork, architecture), historical (tours of towns, churches), food (culinary classes, olive oil mill, winemaking/vineyards), and outdoor activities (hiking, truffle hunting, sunset boating cruise). The uniqueness of some of the activities made this vacation one of the best European vacations we have ever experienced.

The guidance of Zicasso's travel specialists was so appreciated and was spot on for planning meals and when to leave open time. The guides and drivers they provided were extremely knowledgeable, helpful, and very friendly. Even when we had major air travel issues getting to Italy, they immediately came to our rescue when we had to arrive in Florence instead of Pisa.

Also, all of the accommodations which they booked for us were comfortable, spacious, and within easy walking distance of local attractions. We highly recommend Zicasso. We are looking forward to being able to plan our next Italian adventure with them.

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Italy Travel Review: Venice, Florence, Tuscany, Cortona, Sorrento, Amalfi Coast, Capri, Pompeii, Rome, Vatican, Lagoon Boat Trip, Wine Tasting, Cooking Class, 2 Weeks

Our 16-day trip through Venice, Florence, Tuscany, Sorrento and the Amalfi Coast, and Rome was outstanding in every detail. Every transfer ran on time, every guide was knowledgeable and warm, and every hotel was a great choice.

Our favorites were the private lagoon boat trip in Venice, the Brunello wine and cheese tour, the pasta class at a Tuscan farm, Pompeii, the Capri cruise, and the Vatican tour. We couldn’t have asked for better planning or support. We highly recommend Zicasso's travel company.

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Italy Vacation Review: Como, Lugano, Bellagio, Varenna, Lake Como, Boat Ride, Food Tour, 5 Nights

We were so pleased with the travel company. The hotel they suggested was nicely located in Como, with our rooms having a view of the lake and a small balcony. We were also provided a lovely breakfast in the morning.

They suggested a nice, four-day itinerary: a food tour, with the extra bonus of an orientation to the city the evening of our arrival; a wonderful boat ride for four hours on the next day; a trip to Lugano, Switzerland; and then a private transfer, stopping in Bellagio and Varenna on our way back to Milan.

All of the drivers and guides were excellent, although the driver for Lugano thought he was taking us to Bellagio. This may have been due to a switch of drivers due to a schedule change, as the boat ride and Lugano days were switched to make sure we had a beautiful day on the water, as some rain was threatened on the original day.

The travel company also made a lunch reservation in Bellagio for us based on a recommendation we had gotten from our son. The driver for that long day was great about arranging the travel so we could be on time at the restaurant and was there promptly to pick us up when we were done.

We will definitely utilize Zicasso again and would reach out to the travel company if we travel again to Italy.

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Italy Trip Review: Rome, Florence, Tuscany, Cinque Terre, Venice, Pizza-Making Class, 2 Weeks

We had an absolute dream trip to Italy with the help of Zicasso's travel specialist! Traveling as a family of five, we visited Rome, Florence, San Gimignano, Greve, Siena, Cinque Terre, and Venice, along with many beautiful towns and smaller areas throughout the country.

The wonderful vacation rental accommodations were thoughtfully chosen and every detail of our trip was carefully planned. The local tour guides were incredibly knowledgeable and gave us a truly authentic experience. Our private transfers, train transfer, and private tours were efficient, informative, and made traveling from place to place seamless and stress-free.

The communication between all tour guides and transportation providers was great, as was that of each vacation rental host, who contacted us in advance to prepare us for our arrival.

One of our favorite parts of the trip was discovering the smaller, less-touristy areas within the larger cities, places we likely never would have found on our own. We enjoyed exploring Tridente for shopping and Trastevere in Rome for a private pizza-making class (highly recommended), artisan shops, excellent restaurants, and a vibrant nightlife.

Florence was wonderful, but we had the opportunity to travel to a few other areas, such as Siena, Greve, and San Gimignano. We even had a private vineyard tour and chef's meal while in Chianti. A must-see is the walk to the Boboli Gardens across Ponte Vecchio and, on the way back to our apartment, a stop at Piazzale Michelangelo.

While staying in Cinque Terre (Monterosso al Mare), be sure to take a private boat to visit all of the other villages and maybe even snorkel. The water is so clear!

Venice had great history, but we also enjoyed our boat tour to Murano to watch the glassmaking process and Burano, filled with gorgeous multicolored homes and artisan shops.

Every experience felt personal, meaningful, and special.

This trip was truly an absolute dream and we are so grateful to him for helping make our family vacation to Italy unforgettable. We highly recommend him to anyone looking to plan an incredible, seamless, and memorable trip!

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Italy tour Review: Venice, Florence, Milan, Lake Como, Chianti, Cooking Class, Pasta Making, Wine Tasting, Boat Ride, 9 Days

This was our first time visiting Italy, and we were very excited to experience the country through a thoughtfully planned luxury itinerary. Overall, we had some wonderful experiences, but there were also several disappointments that affected our trip and that we feel are important to share.

Highlights

Venice was a highlight of our trip. We loved the atmosphere, scenery, and overall experience of being there.

The wine tasting experience in Tuscany was another major highlight. Our trip to Chianti from Florence was beautiful, and the Tuscan countryside was exactly the type of experience we had hoped for. Our cooking class with our instructor in Florence was also exceptional. Making fresh pasta and tiramisu while enjoying wine, music, and great conversation made it feel authentic and personal. These are experiences we will truly remember.

Areas That Fell Short

We would have appreciated much more advance guidance about how incredibly hot and crowded Italy would be during peak season in September. We experienced a significant heat wave and extremely limited air conditioning throughout the trip, including in hotels and fine dining restaurants. This made traveling much less comfortable than anticipated, particularly as first-time visitors to Italy.

We also visited four cities in just eight days, which in hindsight felt far too rushed. As first-time visitors, we were relying on the agency’s expertise to help us create a realistic itinerary. We would have appreciated being advised that this pace was too ambitious and that fewer destinations with more time in each would have made for a more relaxing experience.

We also did not particularly enjoy Milan and felt there was not much there that appealed to us. In hindsight, we would have preferred to spend more of our limited vacation time in destinations that were a better fit for us.

The Lake Como boat tour was canceled at the last minute because we were given the wrong pickup location. This was especially disappointing because it was an experience we had been looking forward to and had planned our day around. Having it canceled at the last minute due to incorrect pickup information was frustrating and felt avoidable. For a luxury travel itinerary, we expected a higher level of coordination and attention to detail.

Transportation was another area that fell short. The three-hour private drive from Venice to Milan was exhausting, particularly because the driver was blasting music throughout the journey. We also had a four-hour drive from Lake Como to Florence in cramped transportation with limited air conditioning, which was extremely uncomfortable given the heat. For a luxury itinerary, we expected transportation to be spacious, comfortable, and properly climate-controlled, especially for longer transfers.

The hotel in Florence was particularly disappointing. We found the atmosphere to be creepy and uncomfortable and did not feel that the property matched our preference for modern, understated luxury. The shower would not drain properly, and although maintenance told us they had fixed it, the problem continued. The hotel did have an excellent location, a balcony, and warm, attentive staff, which we appreciated, but the overall property was not a good fit for us.

Communication

One area where the agency excelled was communication. The team was consistently prompt and responsive through WhatsApp, which truly became our lifeline throughout the trip. Whenever we had questions or needed assistance, we were able to reach someone quickly, and we very much appreciated that level of accessibility and support while traveling.

Overall

Italy was beautiful, and we are grateful for the opportunity to experience it. However, the trip did not consistently feel like the luxury experience we had envisioned. For future clients, we would strongly recommend providing more candid guidance around itinerary pacing, September peak-season crowds, heat, limited air conditioning, hotel style, and destination selection, as well as ensuring greater attention to detail with transportation and excursions.

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Italy Anniversary Tour Review: 2 Weeks

Our first trip to Italy was a romantic anniversary celebration, and thanks to Zicasso’s travel specialist and our travel company, it became one of the most extraordinary and meaningful travel experiences of our lives. It was everything we had dreamed of, and so much more!

From our very first conversations, she took the time to understand who we are as travelers: our love of art, architecture, history, culture, food, wine, and lifelong learning. She translated those passions into an imaginative, beautifully personalized journey through Rome, Tuscany, Florence, and Venice.

One of her greatest gifts is her intuitive understanding of the rhythm of travel. We wanted days filled with discovery, learning, and new experiences, but also leisurely afternoons and evenings to wander cobblestone streets, linger over wonderful meals, and simply absorb the atmosphere of Italian life. She struck that balance perfectly. Our itinerary was wonderfully rich, yet never rushed or overscheduled.

The private guides she selected were exceptional: not simply knowledgeable, but gifted teachers and storytellers who brought centuries of Italian history, art, architecture, and culture vividly to life. In Florence, for example, our guide helped us explore the Renaissance through fascinating stories of the Medici family, Michelangelo’s creative process, and the philosophy of Humanism. Our visits to the great museums and historic landmarks became intellectually stimulating and deeply engaging experiences.

She also introduced us to Italy’s living traditions: a fabulous food tour in Rome, wine tasting in Tuscany, explorations of enchanting medieval towns and villages, and boat excursions to Murano and Burano, where we discovered the centuries-old artistry of glassblowing and lacemaking. These experiences gave us a wonderful sense of the richness and continuity of Italian culture.

Her choices of accommodations were equally inspired. Each was distinctive, beautifully located, and full of character, from a charming, peaceful boutique hotel near the Pantheon in Rome, to a magical stay in a medieval Tuscan village, an elegant Art Deco hotel in Florence, and a fairytale suite in Venice. Every setting added another layer of romance and delight to our anniversary celebration. And the cuisine was heavenly! Every meal was memorable, culminating in a dreamy farewell dinner beside a Venetian canal.

Behind all this magic was the travel specialist’s impeccable planning, extraordinary attention to detail, and genuinely proactive care. Every transition, from airports and private transfers to trains and boats, was seamlessly coordinated.

One small example perfectly captures her approach. When our train from Florence to Venice was delayed, we contacted the travel specialist to let her know. She immediately reassured us that she was already monitoring our train and had informed our guide in Venice of the delay. There was nothing for us to do but relax, enjoy the ride, and look forward to the magnificence of Venice! That kind of thoughtful anticipation gave us complete peace of mind throughout our travels.

Equally special was her warmth and genuine personal connection. She was always accessible, and we found ourselves exchanging messages most days, not because anything needed fixing, but simply because it was such a pleasure sharing our experiences with her. She combines exceptional professionalism, creativity, and meticulous organization with kindness, generosity of spirit, and a contagious passion for sharing the beauty of her country. By the end of our journey, we felt we had gained not only an extraordinary travel advisor, but also a wonderful new friend.

Italy opened our minds, elevated our souls, and deeply touched our hearts. Our travel specialist didn’t simply organize a magnificent vacation; she opened the door to a country and culture we have now fallen completely in love with.

We cannot recommend our travel specialist and travel company highly enough. For anyone seeking a thoughtfully curated, culturally immersive, deeply personal, and truly unforgettable Italian journey, she is an exceptional choice.

We are already dreaming of returning to explore Sicily and Sardinia with our family, and there is absolutely no question who we will call!

Thank you for giving us far more than a beautiful vacation. You gave us an extraordinary gift: memories, discoveries, and connections we will treasure for the rest of our lives.

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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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