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 2244 reviews
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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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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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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This trip to Italy was a honeymoon trip for me and my husband. We had an amazing time and a wonderful experience with Zicasso's travel company! The planning phase was personalized and easy, and respected our budget. We went to Florence, Rome, Venice, and Sorrento over the course of two weeks. Every hotel was top-notch, the excursions were private, and the people we met were exceptionally kind and professional.
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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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The trip was great. The hotels in Tuscany and Lake Como were great. I highly recommend both. The rest of our trip that Zicasso's travel company put together, which included wineries, hikes, boat rides, a balloon ride, and recommended dinners, was top-notch. Our travel specialist and her team were very responsive. We highly recommend them.
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