Romantic Getaway to Italy & Greece

What to expect on this itinerary
You can never have enough romance on this 14-day tour through Italy and Greece meant for honeymooners and passion seekers, lovers and explorers, adventurers and romantics. Spend your days traversing cities that have inspired passion; landscapes take your breath away and the luxuries rejuvenate your soul. Traverse Italy’s vibrant coasts and stunning countryside, along with Greece’s majestic island, to find unique treasures hiding within the dreamy quality of the architecture and sea, the hills and the sunset, bringing fantasy to life.
Customizable Itinerary
Venice – Romantic Beginnings
Welcome to romantic Venice, where the labyrinthine streets and glistening canals have brought historical passions and luxurious seclusion to anyone in search of a grand vacation. Step onto a water taxi and cruise along the famous waterways where colorful gondolas drift beside the raised, ancient buildings. The wind wafts through your hair; you can see the dome of St. Mark’s basilica edging closer to you. The taxi docks at the basin of your lush hotel that may overlook the splendid open water of St. Mark’s basin.
What's Included:
Venice – Gilded Stone and Waters
Venice – Marvelous Glass
Bellagio – Remarkable Lakeside
Bellagio – A Graceful Way
Bellagio – Villas and Flowers
Portofino – Lake to Riviera
Portofino – One Town to Five Towns
Florence – A Day with the Renaissance
Santorini – From Tuscan Hills to Island Cliffs
Santorini – Colorful Beaches
Santorini – Around the Crescent
Santorini – Thriving Antiquity
Santorini – Disappearing Aegean
Trip Highlights
- Scour the romantic streets of Venice, from Saint Mark’s Square, to the labyrinthine streets
- Visit the famous glassmakers of Murano
- Experience the sapphire waters and lush forests at Lake Como
- Relax along the Italian Riviera
- Visit the charming streets and local gardens of Cinque Terre
- Discover the reasons for Tuscany’s famous countryside by venturing through its rolling hills and medieval villages
- Luxuriate on Santorini’s famous cliffs, where the whitewashed homes and blue roofs are a way of life
Starting Price
$13,700 per person (excluding international flights)
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 970 reviews
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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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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Our Zicasso travel agent did a great job planning and executing our two-week tour of Italy. Transfers were seamless and guides were knowledgeable and experienced. We particularly loved Florence, our hotel, its staff, and its walkable location to so many sites. We loved the guide in Cinque Terre; he knew the area, specifically a restaurant where we were away from the crowds. Thanks to the travel agent for a job well done.
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Our honeymoon in Italy was absolutely magical and so much of that is thanks to our travel company. From our very first call, they took the time to understand what we wanted and crafted an itinerary through Florence, Rome, and the Amalfi Coast that felt personal rather than cookie-cutter. Every detail was handled: hotels, transfers, and tours all ran seamlessly, so we could simply relax and enjoy being newlyweds.
Florence stole our hearts with its art and charm, Rome was awe-inspiring at every turn, and ending the trip on the Amalfi Coast, with those breathtaking sea views, was the perfect romantic finale. The guides were knowledgeable and genuinely passionate, bringing each city to life in a way we never could have experienced on our own.
Communication before and during the trip was prompt and reassuring, and it was clear the team truly cared about making our honeymoon special.
We came home with memories we'll treasure forever. We can't recommend this travel company and Zicasso highly enough. We're already dreaming about our next trip with them!
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Zicasso’s travel agent and her team provided us with an absolutely incredible honeymoon experience. The trip far surpassed our expectations, as every detail was meticulously planned to ensure we were delighted at every turn. From champagne on our boat rides and thoughtful notes at the hotels to a surprise bottle of wine for my birthday, the travel company managed to impress us more with each passing day.
Our itinerary was four nights in Lake Garda, four nights in the Piedmont region, and three nights in Lake Como.
We spent a lot of time selecting the right locations and hotels to find the perfect balance of activity and relaxation, and the team didn't miss a beat. They connected us with exceptional local partners for all of our excursions and were incredibly responsive whenever we had questions during the trip. They were truly easy to work with and planned the trip of a lifetime for us. An easy 5/5. I highly recommend this travel company for anyone planning a trip to Italy.
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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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