Iconic Italy: Fast-Paced Exploration from Venice to Sicily

What to expect on this itinerary
Discover Italy's diverse history, pristine nature, and contemporary culture on this 14-day journey. From hiking Mount Etna to zooming around Rome on a Segway, witness this magnificent country from many different vantage points. Be immersed in Italy's renowned cuisine, discover the wines of Chianti and Sicily, and attend a cooking class in Florence.
Customizable Itinerary
Milan - A Chic Arrival
Upon your arrival, you will be met and transferred by your driver to your accommodation in the heart of Milan. Depending on your time of arrival, you may wish to rest at your hotel or set out for an independent exploration of the city. Milan has emerged as a fashion capital, which is on full display throughout the city, especially in the Galleria Vittorio Emanuele II. You may also wish to visit some of Milan’s architectural gems, such as the Duomo, La Scala Theatre, or Sforza Castle.
What's Included:
Venice - Discover "La Serenissima"
Venice - Wander the Canals
Florence - Discover Florence's Magic
Florence - Lean in at Pisa
Florence - ATV Tour of the City
Sorrento - On the Amalfi Coast
Sorrento - Day-Trip to Capri
Rome - Scoot through Rome
Rome - Secrets at Vatican City
Taormina - Fly to Sicily
Taormina - Mount Etna and Wine Tasting
Taormina - Luxuriate in Taormina
Taormina - Departure
Trip Highlights
- Explore the breathtaking Tuscan countryside of Chianti on quad-bike ATVs
- Skip the line and hunt for secrets at the Vatican Museums
- Visit Florence’s iconic churches and museums
- Embark on an exhilarating hike on Mount Etna with a post-hike wine tasting
- Enjoy a romantic gondola ride through the canals of Venice
- Luxuriate in the classic beauty of Capri
- Visit relics from Italy's ancient past
- Indulge in the diverse cuisines from around the country, from regional dishes to local wine
Starting Price
$6,200 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 762 reviews
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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We had the best time during our wonder trip to Italy. We explored Venice, Tuscany, Rome, and the Amalfi Coast. Zicasso's travel agency arranged the most beautiful hotels, with exceptional service, and fun and exciting tours in each location.
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My wife and I consulted with a handful of travel agencies in order to pick the right one for us to curate our dream honeymoon, and I could not be happier with our final decision to trust Zicasso’s tour company with this task.
Our travel agent was amazing throughout the process of building our itinerary, choosing experiences that fit exactly what we were looking for in an Italy honeymoon.
Start to finish, our overall experience was seamless. We decided to pack a lot into 10 nights, visiting Tuscany, Venice, Sorrento, and finishing the trip with one night in Rome. The tour company perfectly constructed our itinerary in a way that did not make our experience feel rushed in any of these locations. We had ample time to relax and explore these beautiful places on our own, while also fitting in world-class experiences specific to the region in which we were staying, all hand-selected by the tour company and their local expertise.
Every experience we had was incredible. From a private pasta cooking class and wine tasting in Tuscany to a limoncello tour in a quiet, picturesque village along the Amalfi Coast, each will be an experience my wife and I will never forget.
I would recommend this travel company to anyone visiting Italy for the first time or even those who have been to Italy, but want to experience breathtaking excursions curated by a local team of experts.
Our honeymoon was all we dreamed of and more, and I look forward to having the opportunity to use them for our next adventure.
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We had the pleasure of working with Zicasso’s travel agents to create the perfect Italian adventure. I had quite a few specific requests, from travel logistics to hotel preferences, and they were incredibly patient and collaborative, offering multiple variations of the itinerary until it matched exactly what we envisioned.
Our journey began in Venice, where we were seamlessly picked up by a private driver, transferred to a water taxi, and dropped directly at our hotel. After a wonderful stay, we were taken by private driver to the train station for our ride from Venice to Florence, our one and only train trip, as we opted (based on their smart recommendation) for private transportation for the rest of our travels to avoid potential delays and enjoy added convenience.
From Florence, we were driven into the Tuscan hills, where we experienced magical wine tastings, vineyard tours, olive oil tastings, and unforgettable meals with wine pairings.
Next, our private driver brought us to Pompeii, where we enjoyed a fascinating tour with our private guide, and then continued on to Rome. In Rome, we loved the private golf cart tour of the city’s major landmarks, as well as a delightful cooking class that was arranged for us; it was a real highlight!
Finally, we traveled by private driver to Sorrento. From there, we had a breathtaking driving tour of the Amalfi Coast, a lemon farm tour, and an amazing day trip to Capri. Every detail was thoughtfully planned and executed.
Summary:
Planning and Itinerary Creation: Zicasso’s consultants made the entire process easy and stress-free. They worked closely with us to perfect the itinerary and were always receptive to changes and feedback.
Hotels: My sister and I requested adjoining rooms and were provided with beautiful family suites throughout the trip. Each hotel was ideally located, comfortable, and well-appointed, with all the amenities we needed.
Transportation: Every transfer was smooth and punctual. The private drivers were professional, friendly, and knowledgeable. (A special shoutout to our driver in Florence/Tuscany – he was the best!)
Communication: Throughout our trip, the travel company’s team was always accessible. Whether we needed to make adjustments or had a question, they handled everything promptly, allowing us to relax and fully enjoy our vacation.
We spent just over two unforgettable weeks in Italy and it was absolutely perfect, all thanks to the hard work, attention to detail, and excellent communication from Zicasso’s travel company! I highly recommend them and would not hesitate to use them again for future adventures.
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It was a pleasure working with Zicasso’s travel specialist and her team for our recent trip to Italy, including Rome and Sicily. The travel specialist was thoughtful throughout and demonstrated exceptional local knowledge when crafting our itinerary, particularly for Sicily, where we spent seven to eight days exploring the northwest, east, and southeast regions.
The itinerary beautifully blended visits to charming fishing villages with well-paced day tours, allowing for meaningful free time in between. In fact, she strongly encouraged us to include a free day to explore on our own, which made a noticeable difference, as we never felt rushed or exhausted. The hotels were impeccably selected and added greatly to the overall experience.
This was a truly memorable trip that we enjoyed every step of the way.
Thank you to the travel specialist and the travel company for creating such a wonderful experience. We will absolutely turn to them again for our next visit to Italy.
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