Adventure and Romance Tour of Italy & Greece

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.
Customizable Itinerary
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:
Venice - Exploring a Rare and Authentic Venice
Venice - The Art and Antiquity of the Islands in the Venice Lagoon
Lake Como - Travel by Train to the Opulent Shores of Lake Como
Lake Como - Weaving and Wandering Bellagio
Lake Como - Acquaint Yourself with the Romance of Lake Como
Portofino - Travel by Ferry and Train to Your Villa in Portofino
Portofino - Explorations of Portofino’s Landscape, Culture and Indulgences
Portofino - Trave to Cinque Terre to Explore Seaside Terraced Villages
Florence - Disappear into the Heart of Tuscany
Florence - Feel the Inspirational Power of Val d’Orcia
Florence - Explore the Heart of the Renaissance
Florence - Sink into the Rhythm of Florence
Santorini - Travel via Rome to Greece
Santorini - Casual Explorations of Santorini
Santorini - The Beaches of the Aegean Cyclades
Santorini - Dipping Below the Surface of the Aegean Sea
A Lighthouse and Sunset in Akrotiri Caldera Beach
Santorini - A Final Blissful Day in Greece
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.
Verified Traveler Reviews
Based on 2364 reviews
My first solo trip was something I had dreamed about for years. I wanted it to be more than sightseeing. I wanted adventure, comfort, safety, and freedom without the stress of planning it all alone. Through Zicasso, I was connected to two specialists and Zicasso's travel consultant stood out immediately. She delivered an itinerary that gave me everything I asked for and more: maximum cities, maximum fun, and maximum value, all without compromise.
Before deciding, I researched and compared tours, packages, and individual prices online. The travel consultant’s proposal came out on top for value and content. While the other agent offered fewer cities and activities at a higher price, her plan was ambitious without being overwhelming. She booked my trains, arranged private transfers where needed, and selected boutique-style hotels that exceeded expectations. I was honestly surprised at how good they were. I stayed at hotels in Interlaken, Florence, and Sorrento. Each was clean, comfortable, and perfectly located for exploring. I had prepared myself for budget trade-offs, but instead, I found thoughtfully chosen hotels that balanced affordability with real quality.
Every document, train ticket, and activity confirmation was uploaded into the app. It became my lifeline throughout the trip, with every detail at my fingertips. The structure gave me confidence, while still leaving me free to explore.
Switzerland came first: Zurich, Lucerne, Interlaken, and Zermatt. Each city felt like stepping into a postcard. Interlaken gave me the adrenaline rush of skydiving, while Zermatt charmed me with its close-knit magic and alpine beauty. Italy unfolded with equal ease: Lake Como, Venice, Florence, Sorrento, Amalfi, and Rome. Every destination felt curated, yet natural, from gondola rides in Venice to boat tours on the Amalfi Coast.
What I loved most was the balance between structure and freedom. Pre-booked activities and restaurant reservations gave me a strong framework, but I could just as easily decide to spend an afternoon wandering Florence, eating gelato, or sitting in a piazza. The rhythm of the trip was perfect, structured enough to tick off bucket-list highlights, yet relaxed enough to feel like a real vacation.
Food was freestyle, but memorable. Highlights included a Japanese-Peruvian restaurant in Zurich with its elegant Japanese-Peruvian flavors, a different Japanese restaurant, a restaurant in Como with its modern fusion menu, an Indian restaurant for comforting classics, and international favorites like those in one of the restaurants in Rome. Between those meals and plenty of gelato and crepes, every stop added its own flavor to the journey.
As a solo traveler, safety mattered. I felt comfortable walking around in the evenings and was usually back in my hotel by 1am to stay rested for the next day. What really gave me peace of mind was the travel consultant’s constant support. Communication was fast and responsive. I never had to wait long for answers, whether through the app or email. There was a moment when I made a mistake with the trains and missed an activity. She immediately stepped in and worked to reschedule it or secure a refund that same day.
Earlier in the planning process, I also had a card issue due to an address error. Even though policy would not normally allow it, she and her team patiently waited until I received the refund before finalizing the booking, just weeks before my trip. That flexibility and care spoke volumes.
The difference was clear. She used my budget to its fullest potential, giving me more destinations, more experiences, and better hotels than the alternative option. She managed to combine the efficiency of a fully organized tour with the freedom of independent travel. Everything was planned, yet everything was still mine to shape.
This trip was everything I wanted: good food, beautiful views, safety, and absolute reliability. It was an organized journey with freestyle flexibility, which is exactly what solo travelers dream of. The travel consultant’s planning let me chase adventure while always knowing I had a safety net. Switzerland and Italy gave me memories I will never forget, but it was the behind-the-scenes planning that made it possible. If you want a trip that is your way, your budget, your pace, but without the endless hassle of managing it yourself, the travel consultant at this agency is the person who can make it happen. My first solo trip became my dream trip and that is the highest praise I can give.
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Our trip to Venice, Florence, Tuscany, Lake Como, and Milan was exceptionally well planned and executed by Zicasso's tour operator.
The transportation from one location to another was efficient, even when challenged by the high tides in Venice. Overall, the hotels selected were very good. The one in Montalcino was exceptional. Every guide was knowledgeable and professional. We appreciated their willingness to be flexible. Our driver for the ride to Como and back to Milan was personable and exceptional as well.
We really enjoyed the truffle hunting experience, the first wine tasting in Montepulciano, where we met the entire charming family, the cooking class in Bellagio with a chef who treated us like family, and the boat rides on Lake Como and to the islands in the lagoon of Venice. All of the dinner reservations were spot-on and when there was a slight misunderstanding regarding our wine tasting in Bellagio, where the staff at the hotel in Bellagio had no idea what had been arranged by our agency, this was quickly resolved by our guide through texts and emails with the agency.
The only aspect of the trip that could have been improved was day eight, when our activities, travel time, and late dinner reservation resulted in a late-night drive back to the villa. The hotel in Milan was difficult to find at first due to its location not being visible from the street. Once we found it and settled in, it was in an excellent location for our sightseeing. The gifts of sparkling wine at two of our stops was thoughtful and appreciated.
We thank our agent and the staff at the agency for a wonderful trip and would not hesitate to recommend the firm to our friends and family.
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When we started planning our trip to Italy, I knew I wanted to work with a travel agent—specifically, someone who specialized in Italy and was based there. After reaching out to several agencies and reviewing their responses, we chose Zicasso and, more specifically, our travel agent. She is based in Milan and from my very first interaction with her, I knew we had made the right choice.
Our trip could not have been more perfect. Our agent put a lot of thought into every location and planned activity. At the outset, we had a few discussions with her about what we wanted from the trip and, after that, we were happy to leave most of the details in her capable hands. Our goal was to explore mid-to-northern Italy and everything—from the hotels and tours to the free time and transportation—was beautifully organized.
Our 11-night trip started in Milan and ended in Florence, with overnight stays in Milan (one night), Lake Como (three nights), Venice (three nights), and Florence (four nights). Initially, I was hesitant about staying at Lake Como for three nights, but our agent encouraged me to do a little research. I’m so glad she did, as it turned out to be incredible. We had more self-guided time at Lake Como, which was perfect as we adjusted to the time change. In Venice, our itinerary became more structured, but we still had plenty of time for our own explorations. By the time we reached Florence, we had activities and tours planned for every day, which was just what we wanted.
A highlight for my family was a full-day trip into Tuscany, where we visited San Gimignano, an organic vineyard in Chianti, and finished with a tour of Siena. Our day trip to Rome allowed us to see the main attractions and we concluded the journey with a tour of Florence and the Accademia Gallery. Every tour our agent arranged was spot on.
Throughout our trip, she was wonderfully communicative—always available when we had questions, but never intrusive. She even helped us with a couple of last-minute requests: booking a hotel in Milan for one night and arranging train tickets to Verona for an impromptu visit to Juliet’s balcony. Whenever we needed something, she was there.
When we return to explore the mid-to-southern part of Italy, there’s no question that we’ll be asking her to plan our trip again. I highly recommend her to anyone looking for a seamless, thoughtfully curated Italian adventure.
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Zicasso's travel agency far exceeded our expectations. We had our five-year-old and 11-year-old children with us, so the tour guides and walking needed to be kid-friendly.
Our hotel in Rome was wonderful, the location was perfect, and they had good A/C and a breakfast buffet. There were plenty of great restaurants within easy walking distance, as well as the Vatican.
Our tour guide for the Colosseum and Roman Forum was great. Pompeii was amazing. Our tour guide was basically a celebrity down there and knew exactly how to take us around the ruins without ever waiting.
Tuscany was our favorite by far. We did a cheese-making experience and lunch that was super-cool. The kids got to play with the farm animals and the owners were so attentive and interesting. We did a cooking class with a chef that was the kids' favorite thing on the entire trip. I would make a point to book this experience; the kids still talk about it and wear the aprons around the house. The resort in Tuscany was nice. We had our own private pool, plus the resort pool, and could easily walk to a small local town with some great food.
Venice was good, but probably our least favorite on the trip. You have to walk a ton, which was difficult for the kids, but it's still worth experiencing.
We travel a bunch and I would highly recommend using Zicasso's travel partner.
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We enjoyed all of the planned tours in Italy and Greece. Favorites included the Vatican, Colosseum, Roman walking food tour, and a day exploring the Tuscany wine region.
We loved all of our hotels (favorites being our hotel on Via Emilia in Rome and then our hotel on Nikodimou Street in Athens). All of our drivers at our various locales were always on time, even early, and were friendly and engaging.
We did have various questions come up and any time of day/night, Zicasso's travel professional and the tour company were responsive and so helpful.
Our long-awaited 45th anniversary trip came off seamlessly. I appreciate all of the time and planning that went into planning our venture. I will happily recommend you to our friends and family.
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This was my third customized trip with Zicasso. I previously worked with Zicasso to plan and take mother-daughter trips to Iceland and Croatia. They are the perfect company to help your dreams for a personally unique adventure come true!
This time, I traveled with my daughter, son, and daughter-in-law to Italy. My hope was for my daughter and son to see the towns where their great-grandfather and great-grandmother emigrated from in the Abruzzo region, in the towns of Roccamontepiano and Bugnara. My research had an address for where their great-grandfather was born. Our driver found the address and we took photos of us standing in front of the house, which could now be considered a real fixer-upper. Just the same, it was a moment never to be forgotten. Thank you to our driver and his wealth of information!
Our home base was in Pescara, where we enjoyed a walk on the beach, excellent local cuisine at a local restaurant, and seafood at another local restaurant. These were recommended by our local travel agent and were clearly favorites of the locals.
We had a wonderful tour in Chieti, an historic and cultural gem, with our guide. She too was a gem of a guide!
We then traveled to Venice, which was far less crowded with tourists than in the high season. Upon arrival, a private gondola ride during dusk and at sunset was a surreal way to be welcomed to this beautiful city.
The next day we had a magnificent tour of St. Mark's Basilica and Doge's Palace. Our guide was so engaging and knowledgeable, and eager to share ideas about other things to see while in Venice. We followed our tour with lunch at a historic restaurant, home to the invention of the Bellini. Yum! After lunch, we took the elevator to the top of the tower across from the basilica, with its spectacular panoramic view of the city and surrounding islands. Then our group splintered off—two of us did a Grand Canal boat ride and the other two headed to the isle of Murano to search for glass souvenir treasures.
Our next stop was Lake Como, with a one-hour unexpected stop in Verona. Thank you to our driver for suggesting the stop! Who knew there was a Roman arena and some to-die-for hot chocolate in Verona!
Then off to Lake Como. We had time before we could check in to our hotel, so we did a walkabout to acquaint ourselves with the city. We took a ride on the funicular for another delightful panoramic view and enjoyed cocktails while surveying the lake and city below. That evening, we traveled up into the mountains and had a marvelous meal at a mountain trattoria. We were just us and one other couple in the restaurant, and we watched the chef prepare our local food specialties from our table in front of the wood-burning fireplace. The mantel was adorned with trophies and photos of the local bocce teams over the decades. Again, if you want to travel for cibo delizioso, go to Italy!
The next day, we had a three-hour boat ride on Lake Como. Our skipper and guide made certain to point out and give some history on the villages dotting the coastline and the famous villas.
The following day we traveled north to Domaso for an afternoon at a family-run vineyard and restaurant with views of Lake Como and the Alps! Bellissimo! A family member gave us a wonderful tour of the history and the winemaking facility, as well as the many wines we sampled. We were treated to local charcuterie and ravioli that was made fresh while we were busy sampling. When we received the wine we ordered and shipped back home, they threw in extra gifts for us, with wishes for a Merry Christmas and Happy New Year!
Then we were off to Milan for a chance to try our luck at making our own pasta, sauces, and gelato at a cooking school. Our chef instructor guided us as we made tagliatelle with a pesto sauce and pumpkin ravioli with a cream sauce. Of course, there were wine pairings! He made certain our creations were delicious!
That evening, we donned our fancy apparel and headed to La Scala to take in the opera, "Così fan tutte." The modern take on the comedy was refreshing and the venue was a must-see!
The next day, we were met by our guide, who shared the history of the UNESCO site of Santa Maria delle Grazie and Leonardo da Vinci’s "Last Supper" with expertise and reverence, while keeping us engaged. She likewise inspired us as we toured the Duomo di Milano, San Maurizio al Monastero Maggiore, and the controversial Il Dito sculpture outside the city’s stock exchange.
That evening, we experienced a delightful meal at a Michelin-starred restaurant. The chef, from Naples, created and explained a never-to-be-forgotten bite-sized sampling plate highlighting the tastes of Naples on a plate shaped like the region, with its various borders.
Before leaving Milan, we had a tour of La Scala and its adjacent museum with our guide. She provided us with a history lesson that was quite interesting. That night, we dined at a local seafood restaurant, another treasure clearly favored by the locals. Our waiter was a gem and sent us off with the gift of a bottle of wine.
Our final stop was Turin. Once again, we divided—two of us visited the National Museum of Cinema and the panoramic lift housed in the museum. At the top, we gained a wonderful sense of the city,and the cinema museum was a fun surprise! Our other two toured the Juventus Museum and Stadium, and they thoroughly enjoyed their experience as well.
Our final day, we met our guide, who spent the entire day with us, with only a short break, beginning with a gourmet food tour of traditional Piedmont dishes. Along the way, she shared insights into the history and cultural significance of the foods. Later in the day, she guided us through the Royal Palace of Turin, including the Holy Shroud Chapel, Armory, and Museum. Once again, we were treated to a knowledgeable and entertaining guide.
We departed the next day, leaving with priceless memories of our Italy adventure.
Thank you so much to Zicasso’s travel agent. You helped make our trip come true with such care. Grazie mille!
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