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 8604 reviews

Maria S.
Italy Trip Review: Ciociaria, 2-Week Trip

Our trip to Italy was absolutely amazing. Zicasso’s travel company provided exceptional service and attention to detail. We had never used a travel company for arrangements prior to this trip and we are so glad we did. It made the trip stress-free and truly over-the-top.

Our favorite time on the trip was at a location recommended by our travel agent in a very small area called Ciociaria. We loved this location and our resort in Ciociaria. The staff was incredible and we felt so relaxed.

I have been telling all my family and friends about the travel company’s services and that I will use them for future trips. I am so thankful to Zicasso for connecting me to an incredible experience with our travel company.

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YUMEI X.
Greece Tour Review: 6 Nights

Zicasso’s travel agent truly knows what is best for her clients. Without her, we wouldn’t have made the same choices or had nearly as much fun. She is transparent, laying out options along with their pros and cons, which we really appreciated and have not always experienced with other travel agents. Every request and arrangement was delivered as promised, with no miscommunications—again, something we greatly value. All in all, working with this travel agent for our Greece tour was a very positive experience.

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Andrew A.
Italy Family Vacation Review: Rome, Florence, Mount Vesuvius, Wine Tasting, 10 Days

This was our first time using a travel agency for a trip like this and Zicasso’s travel company completely exceeded our expectations. Traveling internationally with pre-teen children can be stressful, but from the very beginning, this travel company removed every bit of that anxiety. Every detail was thoughtfully planned, clearly communicated, and flawlessly executed.

From airport transfers to hotels, tours, trains, guides, and daily logistics, everything worked seamlessly. We never once felt lost, rushed, or unsure of what was next. Instead of worrying about schedules or navigating a foreign country, we were able to fully focus on our family and enjoy the experience. That peace of mind alone was invaluable.

What really stood out was how well the trip was tailored to our family. The pacing was perfect, the experiences were engaging for adults and kids, and every guide we worked with was knowledgeable, friendly, and professional. It truly felt like a curated, high-quality experience rather than a generic itinerary.

We came home with incredible memories and zero travel stress, something I didn’t think was possible with kids that age. This travel company was phenomenal and we would absolutely use them again, and recommend them without hesitation to anyone considering international travel, especially families.

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Michael E.
Italy Vacation Review: Venice, Florence, Rome, Sorrento, Murano, Burano, Pisa, Vatican, Colosseum, Pompeii, Capri, Private Tours, Cooking Class, 10 Nights

I apologize for the delay in writing this review, but was very busy the last few months and wanted to dedicate the time it deserved. This review will address my wife and my trip to Italy from September 26, 2025, to October 6, 2025. Please feel free to share all or any portion of this review.

Trip Planning:

As a bucket-list event, I spent a great deal of time doing research, but would not have been able to put together the ideal vacation without the support of Zicasso and the travel company. Upon hearing my general interests, Zicasso provided two groups whom they thought would be able to plan and implement my trip. Both groups interviewed me and my wife about interests and price range, and then prepared an initial itinerary. Both groups would have done a fantastic job by their presentation, but it seemed I was slightly more in tune with the travel company and selected them. This proved to be a very wise choice, as the entire team at the travel company, particularly the travel specialists, were the absolute best and I would recommend their service without reservation. Fully responsive to my many questions before the trip, addressing all potential itinerary changes, and providing invaluable guidance throughout the entire process. Their response to inquiries while in the country was unbelievably prompt and thorough. At our request, the travel specialists made restaurant recommendations and reservations that were spot-on. I can’t say enough good things about these ladies.

Transportation and travel between locations:

Although not involved in the flights, the travel specialists provided great guidance concerning flights, trip insurance, and other logistics.

One key point that I fully expressed was that I did not want to flounder at the various transportation points and did not want to lug luggage in foreign areas on the way to and from lodging. The team took this to heart and provided me with either an escort or driver to and from every terminal. Everyone providing this task was friendly and provided information that made the travel much easier. Particularly valuable were our escorts, who adeptly negotiated our entrance and exit from Venice, and provided great insights into this historic city.

Venice:

Our hotel in Venice seemed to be right in the middle of everything, which allowed us to explore, and we have never had so much fun getting lost. At night, we opened our windows and fell off to sleep listening to nearby music; it was idyllic. The staff was professional and friendly. Breakfast was the best of all the hotels we stayed at in Italy.

The first full day in Venice, the travel company leveraged “skip the line” so we could make the very most of our time and is essential to any planning. Both guides were great and really good company. One guide’s knowledge of the Doge Palace really brought it to life for us. Another guide had a real insider’s view of Burano, as this was her family’s island. As private tours, we could go at our own pace, which we really liked. Probably the least enjoyable tour was the glass factory in Murano. We got the impression most of the tour beyond the initial exhibition was an attempt to sell their products. My wife succumbed and purchased a pair of earrings that broke the first time she wore them. Really disappointing, and I would advise you to spend more time in Burano.

Florence:

As with all the trains, the travel was very comfortable and we enjoyed watching the scenery. Our lodging in Florence was right on the Santa Maria square, superb for people watching. The staff was fine, nothing more. The hotel was near the world’s oldest pharmacy, famous as the world's oldest perfumery. Although there is a line to enter, it goes quickly and is historical, to say nothing of buying a scent more than 400 years old. I strongly recommend you go.

While knowledgeable, our tour guide for the Accademia and Uffizi Galleries was a little too technical for us, leaving us with the feeling that we were taking an art history class.

Dinner was based on the travel specialist's recommendation and it was delicious. A strong recommendation.

Day trip to Pisa:

The travel arrangements were perfect. The purpose of the trip was to take the obligatory picture holding up the tower—hokey, but we loved it.

The private cooking class with our instructor was a lot of fun. The view of the city from her window at sunset was beautiful. My wife and our instructor fell into a real rhythm cooking, and she was kind enough not to scoff at my ham-handed attempts. Her directions were simple enough for me to follow, theoretically. She followed up her lesson with an email containing detailed recipes. We have purchased all necessary utensils and are planning a pasta-making party soon. This was a fun change of pace.

Rome:

Our bed-and-breakfast in Rome was our least favorite lodging. Entry into the building was confusing and, as a B&B, the desk was not manned all the time, which made it difficult to secure a taxi early in the morning (we had to walk to a nearby hotel) or get assistance after 8pm or before 6am. When we came in, we attempted to coordinate laundry service with the person working the front desk, followed his instructions, but when we returned the next day, our dirty clothes were still where we were told to leave them. The initial response from the on-duty staff, who I believe was the owner, was that the individual was no longer an employee. Ultimately, the hotel comped and completed our laundry, which was nice. We would have preferred different lodging.

Our first afternoon, we took a four-hour golf cart tour, which was our favorite tour of the entire trip. Adding an extra hour to the traditional length and having only my wife and me allowed us to do everything we wanted to do. Our driver took us everywhere. He would drop us at the top of the Spanish Steps and meet us at the bottom, and would conveniently bring us closest to all other locations. I can’t believe how much we did in four hours. Our driver brought all these iconic sites to life with his marvelous insight and provided a great insider view of these monuments. This is a must-do for all first-time visitors to Rome. The only thing we were not able to do, due to no fault of our driver, was the Aventine Keyhole. When we got there in the afternoon, the line was 45 minutes and not a wise use of our time. If this is a strong interest, he recommends going early in the morning.

The travel specialists arranged tickets for the Papal general audience on Wednesday. Rising at sunrise was worth it to get the seats as close as we were able to secure. Most online sites suggest getting there an hour and a half before the start time, but I think that is much too late. I recommend you get there three to four hours ahead to get the best seats. The best seats are on the end near where the Pope drives by, ideally near an infant, and His Holiness will stop to personally bless these children. Facing the stage, the right side filled up quicker than the left side, so go directly to the left side of the audience. Being so close to the first American-born Pope was a memory I will never forget. His Holiness blesses all items in the audience's possession, so load up on rosary beads; they will make great Baptism and Communion gifts.

The afternoon was our first group tour at the Vatican Museums. It might be that we were spoiled with the previous private tours, but linking up with the group was chaotic and the quality of the tour was contingent on those in our group. Fortunately, all our groups were good, considerate, and friendly people. The main value was skipping the line for entrance. As with the Doge Palace, our guide was a little too academic and didn't really manage time well, potentially a victim of being in a group, but I would have rather spent more time in the Sistine Chapel and the Basilica. Taxis were extremely hard to get back to the hotel and I would arrange a ride if I were to do it again.

The Thursday tour of the Colosseum and Forum was also a group tour, but led by a guide who brought this ancient land to life. An archaeologist by trade, our guide seemed to know everything and also took a great picture.

The end of a very long but enjoyable day was another group tour of the catacombs and Santa Maria Maggiore. While the catacombs were the main attraction, the after-hours and behind-the-scenes access to Santa Maria Maggiore was an unexpected gem. Going through a second Holy Door, viewing the magnificent nighttime skyline from the roof, seeing the location of a relic from the baby Jesus’ manger, and being struck by the modesty of Bernini’s and Pope Francis’s tombs were all highlights. Unfortunately, taxis were again hard to come by.

Sorrento:

We took a train from Rome to Naples. While there was a national strike, it did not prove more than an inconvenience, no worse than New York City on a regular day. Our driver from Naples told us this simply provided us with a genuine Italian experience. I wish I could remember this driver’s name because he was the best of a very good group of drivers during this trip. En route to Sorrento, we stopped for a tour and meal at a winery and a private skip-the-line tour of Pompeii. We were so impressed with the quality of the winery that we made a large purchase of wines and olive oils that, thankfully, included free shipping.

During our drive to Sorrento, our driver took us through his hometown, which we really enjoyed. Going through the town, he pointed out the birthplace of Bruce Springsteen’s mother. Little did he know, we were from New Jersey and are HUGE Springsteen fans.

Our hotel in Sorrento was a nice place, close to the center of town. I would have preferred a hotel with a view of the coast.

On Saturday, we took a private tour up the coast. This was the most comfortable car I have ever ridden in, with heated and cooled seats, and a convenient icebox. The driver made clear he was at our disposal. The scenery was marvelous and it was a thrill to dip our toes in the Med. Our driver hooked us up with a restaurant on a cliff overlooking the water—beautiful and scrumptious.

Our last day was supposed to be the Gozzo tour of Capri, but was canceled due to weather. We refunded the canceled boat tour, but ate the driver and ferry fees. In hindsight, knowing this day was largely contingent on weather, I would have liked to have a contingency plan and would advise the travel company to plan this in the future.

Based on how smoothly things went, we will be contacting Zicasso to arrange a trip to Iceland and Ireland next fall, and hope they can refer a team as talented as this travel company.

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Susan F.
Italy Anniversary Trip Review: Rome, Orvieto, Siena, Montepulciano, Chianti, Florence, Bologna, Venice, Wine Tasting, Food Tour, 2 Weeks

Thank you to Zicasso’s travel specialist and her amazing staff. The itinerary was fabulous. It was filled with food, wine, and highlights of the most important tourist places. Her guidance throughout the year-plus planning was the right amount of checking in and waiting. Thank you for the nudges to have reservations for all the holiday days. Things seemed to be pretty open overall, but it was nice not to worry.

All the restaurants set up for us were wonderful. The app was terrific to keep track of what we were doing when. All the drivers were very friendly, professional, and punctual.

Thank you for making our 35th wedding anniversary trip (December 22 2024 to January 6 2025) a most memorable one. We hope to return to Italy to enjoy the southern area and maybe some of the beaches and islands.

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Mary J.
Italy Tour Review: 11 Nights

We had an excellent itinerary and we really liked the accommodations provided, and their locations within walking distance of our must-see sites.

Excellent tour guides, drivers, and transportation were provided!

The Zicasso travel expert's recommended restaurants were also great and the guidelines were helpful!

My husband and I saw and enjoyed what we needed to see and experience!

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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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