11-Day Luxury Wine Tour of Tuscany

What to expect on this itinerary
With layers of wine and preserved tradition to guide you, your 11-day Tuscany luxury tour revels in art from the museums to the kitchens, the piazzas to the markets. Witness architectural grandeur, sample the delicacies of restraint, and embrace the essential tastes of the grapevine. The Uffizi to Montepulciano’s terraced vineyards, the Accademia to San Gimignano’s towers, when discovering Tuscany, even the simple can feel opulent.
Customizable Itinerary
Florence - Arrive in Captivating Florence
Florence is a small city overflowing with the past, from grand palaces to palatial museums, masterpieces of renowned artists to an essential connection to the surrounding countryside. Your flight will land at Florence International Airport, where your private transfer will greet you upon arrival. Once inside the city, you will have a direct view of Medieval streets and Renaissance glamour as you check in to the comforts of your luxury accommodations. The remainder of the day will be at your leisure to absorb the pace of an Italian city as the cobblestone lanes fill with restaurant tables and evening light.
What's Included:
Florence - Bask in the Beauty of Florence
Florence - Uncover Masterful Art
Chianti - Embrace Charm in Chianti Villages
Chianti - Sample Tuscany and San Gimignano
Val d’Orcia - Discover the Beauty of Siena
Val d’Orcia - Enjoy a Cooking Class and Market
Val d’Orcia - Explore in and around Montepulciano
Val d’Orcia - The Cheese and Cuisine of Pienza
Rome - Depart for Home
Rome - Depart for Home
Trip Highlights
- Witness the exceptional detail and size of Michelangelo’s David on a private tour of the Accademia
- Discover the wonders of the Uffizi Gallery with a private guide to view masterpieces from artists like da Vinci, Giotto, and Botticelli
- Embrace the delicate and layered flavors of olive oil when visiting a family-owned farm and mill for a delicious tasting
- Indulge in the welcoming ambiance of a family-owned vineyard in the hills of Montepulciano, where you can explore the cellars and taste the noble Italian wine
- Explore the depths and heights of San Gimignano at your pace to view the prestigious towers and walls of the medieval hilltop town
- Enjoy the dramatic ambiance of Siena as you stroll the cobbled lanes at leisure to view the highlights, including the Gothic art and architecture of the cathedral
- Bask in the exquisite flavors of Tuscany during a private cooking class and local market visit to learn how to make a deceptively simple Tuscan menu
- Sample the bold and robust flavors of typical cheese from Pienza after visiting the town known as the embodiment of the Renaissance
Starting Price
$10,800 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 41 reviews
The travel professionals at Zicasso’s travel company worked with us for over a year to plan the most amazing 14-day tour of Venice, Florence, and Rome. They were beyond patient and kind, fielding my endless questions and providing assurances for every detail. Every day was jam-packed with guides and travel. Well, one really doesn't know until you get to Italy, right?
Upon our late-evening arrival to Venice, we had our personal escort waiting for us at the airport, with private transport to our hotel in Venice. She did not leave until we had our bags in the lobby. I knew right then and there we had made the right choice with the travel company.
We found that everything was taken care of by the travel company, down to the smallest detail. Every guide, and there were many, came to our hotels to greet us and escorted us back to our hotel upon conclusion of our tour. Every single guide was a treasure. We never had to hail a taxi, which to me was the most amazing thing, as the travel company had private drivers picking us up or waiting for us at hotels and train stations.
Upon leaving Venice for Florence, our personal escort from the airport was waiting for us at the hotel, with a water taxi to the train station. She walked us through the train station and showed us how to find our gate for our train to Florence. Upon arrival in Florence, we had a private driver waiting for us for transport to the hotel. Same from Florence to Rome, Rome to Naples (for Pompeii and back to Rome).
We had multiple food tours and they were all amazing. We spent every day with private guides. Believe me, the travel company knows the very best guides in Italy. They are there 24/7 for you if things don't go as planned. Trust me on this.
In Venice, our tickets for St. Mark's Basilica that were reserved for our guide disappeared. There we were, no access. Our guide tried to secure tickets on her own and access was sold out. She called the travel company, which somehow secured access, even to the second level, where we could visit the four bronze horses.
Did I mention our day in Tuscany? The travel company insisted we were spending too much time with tours and insisted we take a day in Tuscany. We visited a vineyard in Tuscany for what turned out to be a private tour and lunch hosted by the vineyard owner. We had a table set up overlooking the vineyard and indulged in what may have been the best food we experienced in all of Italy. Everything was made on-site and perfectly paired with the vineyard wines. We were entertained by her three wonderful dogs, two of which were lovable and goofy Labrador retrievers. What a perfect day!
Without a doubt, the travel company is the finest travel agency we have ever had the privilege to work with. As I said earlier, everything was taken care of, nothing was missed: drivers, trains (business class), guides, food tours. The best vacation we have ever had.
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This was the easiest and most wonderful tour experience we have ever had. From the day we contacted Zicasso and were immediately contacted by our Italian "luxury travel" company, we knew we were in good hands. Our travel consultant listened to us and created a plan that was beyond outstanding!
Our drivers were magnificent! We were greeted with signs when we disembarked our ship and when we got off the train. The drivers who came to our hotels were on time. Although they weren't "guides", the two we had for our all-day tours knew history and lots of interesting things that we found fascinating.
When it looked like we would not be able to go to a luncheon and wine tasting due to the Amalfi Coast's winding roads and a bout of car sickness, our personal contact actually called the supplier and found an alternate route. What incredible service!
Zicasso made our first step easy... the travel company made our 50th-anniversary trip over the top!
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We chose Zicasso’s travel company to organize a nine-day trip to Venice, Florence, and Rome for our family of four adults. My wife and I are in our 50s and our two sons are in their early 20s. We all love to travel, but have a range of interests when it comes to experiences, activities, and cuisine. The travel company created an itinerary that gave each of us something memorable.
Everything was planned and executed with care. Hotels were thoughtfully selected, transportation kept us moving without feeling rushed, and every tour guide was exceptional. The team also checked in periodically to make sure we were having the best experience possible. We've traveled internationally many times and this ranks among the very best.
Nine days is just a taste of what Italy has to offer, but our "sampler" tour left all of us excited to return and explore more.
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Our recent trip, planned by Zicasso's travel specialist, was absolutely outstanding and truly exceeded our expectations. We loved the experiences she arranged, including the excursions, cooking classes, wineries, private guides, drivers, and occasional dinner reservations. Everything was seamless, beautifully organized, and completely stress-free.
She clearly listened to what we enjoy and created exactly the kind of trip we love: comfortable, scenic, relaxed, and filled with memorable local experiences. The pacing was excellent, the hotels were as advertised and wonderful, and each day felt thoughtfully curated and different.
Her assistant was also excellent with logistics and quick replies. We especially appreciated the travel app, which was easy to use and updated regularly throughout the trip. On the few occasions when we needed to reach the travel specialist or her assistant directly, they always responded through WhatsApp within about five minutes, even a couple of times after 5pm. That level of responsiveness gave us great peace of mind.
This was a fabulous, stress-free, “cruising-on-land” experience through areas we knew very little about in Puglia, southern Italy, and Sicily. We would enthusiastically recommend the travel specialist and her team, and we would be very happy to work with them again.
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