
Tuscany Tours & Vacations
The emerald rolling hills and expansive rustic landscapes of Tuscany have captured and inspired imaginations for millennia. Discover grandiose castles and medieval abbeys nestled in the hidden countryside. Explore the timeless and classic influences of the Renaissance, which sparked a cultural movement that forever changed the world.
Explore Our Trip Ideas
Let these itineraries inspire your personalized travel experience

8 Day Trip IdeaFrom $3,700
Extraordinary Tuscany Vacation: Countryside, Riviera & More

14 Day Trip IdeaFrom $13,700
A Perfect Private Tour of Tuscany in 2 Weeks

8 Day Trip IdeaFrom $3,600
A Foodie's Slow Tour of Tuscany

8 Day Trip IdeaFrom $3,600
Tuscany Tour for Lovers: Siena, Cortona, Volterra, San Gimignano and Certaldo
How Zicasso Works
Here's how we create life-enriching, luxury travel experiences
1.Share Your Travel Dreams
Zicasso specializes in custom tours, vacations, and safaris tailored to your interests and preferences. From private African safaris to culinary experiences in Europe, submit a trip request to share your ideas and travel style.
2.Meet Your Travel Specialists
To ensure a personalized experience, we'll carefully handpick and introduce you to two of our top travel specialists, each with unsurpassed destination knowledge and local insight aligned to your luxury travel dreams.
3.Design Your Perfect Journey
Compare the expertise of two specialists with itineraries crafted exclusively for you. You can refine these further and choose your preferred proposal. Our unique process ensures a more creative, personalized, and expertly crafted trip.

9 Day Trip IdeaFrom $4,100
Culture of Tuscan Wine & Cuisine Tour

9 Day Trip IdeaFrom $4,100
An Italian Wine Tasting Journey: From Piedmont to Tuscany Wine Tour

8 Day Trip IdeaFrom $3,600
Tuscany Tour of Medieval Cities & Renaissance Preserves

16 Day Trip IdeaFrom $7,200
Tour of Italy: Milan, Lake Como, Venice, Tuscany & Rome

10 Day Trip IdeaFrom $4,500
Finest Wines of Tuscany & Central Italy Tour

7 Day Trip IdeaFrom $3,200
One Week in the Tuscan Countryside Tour
More Vacations in Italy Near Tuscany
Reviews of Zicasso's Tuscany Tours & Vacations
Based on 2819 verified traveler reviews.
My husband and I just returned from a two-week vacation in Italy. With the help of Zicasso and our travel company, we were able to fit every wish into this short time.
We started out in Rome, then went on to Florence for some amazing history. We then traveled to the Tuscany and Chianti countryside for private cooking and wine experiences. We loved the small villages we explored and the little family-owned wineries and olive farms.
A highlight was staying in a bed and breakfast in Ponzano that overlooked the beautiful olive gardens and countryside. We explored the small villages of San Gimignano, Montepulciano, and Montalcino, and felt like we had discovered authentic local life.
The tail of our trip was spent in the beautiful Lake Como area, with a day trip to Lugano, Switzerland.
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THE BEST VACATION EVER!!!!
I must admit that I was somewhat uncomfortable arranging a group tour to Italy with someone I communicated with only via the Internet and telephone. However, after my first communication with our agent -- I knew that she “had it.” She understood exactly what we wanted to do. She was right-on in both concept and execution.
Our ten-day adventure in Italy began with a private transfer with an English speaking local driver from the Rome airport to our fantastic 3 star boutique hotel located right in the historical center of Rome. During our three days in Rome, we had fantastic private tours of Ancient Rome, the Coliseum, and the Vatican Museums. Extremely knowledgeable, English-speaking guides led all of our tours. Sense of Italy had arranged for VIP, skip the line, priority entrance for all tours -- saving us from long waits in long lines.
After our busy 3 days in Rome, we departed via private van transfer from our hotel in Rome to the Chianti Region of Tuscany. The transfer included stops on the Val D’ Orcia to visit the amazing Villages of Montalcino and Montepulciano. The “light lunch” and wine tasting we enjoyed in Montalcino was one of the highlights of our trip. In Tuscany we stayed 7 Nights in a beautiful, historic villa located on one of the best wine estates of Chianti (Villa Le Corti near San Casciano) where we were met with a fantastic welcome dinner. During our time in Tuscany we were transported by private van from our villa to private tours of Siena, San Gimignano, Florence, Pisa and Lucca. On each of our stops we were met by knowledgeable English speaking guides that clearly were proud of the history of their country, and were anxious to share it. Interspersed in all of this activity were numerous exceptional meals with opportunities to taste (and drink) very fine Italian wines.
When we finally were forced to leave Italy, our agent arranged for private transport accommodating our varying departure times from the Florence airport and train station.
Thanks to this travel company and our agent for designing the perfect vacation for our group. The only complaint that I heard was that we ate too much — wow was all the food delicious. I really don’t know how she did it. All of the tours were great — the van drivers friendly and helpful, the guides knowledgeable, and the sites spectacular. Our stay in the villa was a great experience. We were treated royally everywhere. We all marveled at our agent's ability to get us, the vans, the guides, the food and wine, etc. all at the right place at the right time. She is a genius!!!!
Jeff E
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Our family of five just got back from the most wonderful vacation in Tuscany and Rome. Our agent crafted a set of amazing experiences for our family from the private tour guides to Florence, Pisa and Lucca; a private wine tasting lunch at the Capannelle Winery and vineyards in Chianti; tickets to the Papal mass at the Vatican; to a tour beneath the church of San Clemente to see the excavations of a byzantine and then a Roman street neighborhood; a day excursion to the Amalfi coast to visit Positano, Sorrento and Pompeii; and more! Our agent and the guides found excellent restaurants from a simple salumeria where the locals ate to some high end restaurants. The hotels were right in the center of Florence – on the piazza della Repubblica - and Rome – between the Piazza del Popolo and the Spanish Steps. Our agent was attentive to our plans and made excellent suggestions. Everything went extremely smoothly. All the guides drivers were very friendly, spoke English and were very knowledgeable about art, history and the local culture. We saw so much every day because everything was so well planned. Simply the best travel experience ever!
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Wonderful 10 day trip to central Italy planned by this Italy travel company. We spent the first part of the trip at Castello di Casole in the Tuscan countryside, then Florence and the final part of the trip in Rome. While in Tuscany, we took day trips to Montalcino, Siena, Montepulciano, Pienza, San Gimignano and Greve. We had walking tours in Florence and Rome. our agent at this travel company planned all the details, transfer drivers, tour guides and hotel arrangements. Everything went according to plan and was of outstanding quality. The agency gave us a very detailed package of information with all the relevant details for each day.
Great Vacation
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~~OUR STORYBOOK VACATION CREATED BY ZICASSO
The most beautiful vacation was created for my husband and me by this agent, partner of Zicasso. At our initial contact with Zicasso, we advised them of our dream vacation which we wanted in the Tuscany and Umbria regions of Italy. Very soon thereafter we received an e-mail from our agent wanting to know what we wanted to see and do on this vacation. We provided a short list of our desires and she got to work.She contacted us by phone from Florence, Italy where she is located and spent 45 minutes getting to know us and detailing the itinerary with us. That was only the beginning!Within a few days, she set up the itinerary which was perfect for us. We began our journey by flying to Venice (a gondola ride was scheduled, of course). A couple of days later, took a train to Florence (beautiful experience, because our reservations and tickets were already in hand). A private driver met us at the platform and took us to our hotel). A few more days and we were off by rented car (already paid for and ready to go thanks to our agent) and drove off to other parts of Tuscany (Radda in Chianti, Montalcino, Bevagna and the small villages along the way of Volterra, San Gimignano, Siena, Val d’Orcia area with the beautiful Abbey of Sant’ Antimo and listening to the spiritual and beautiful Gregorian chants during Mass, followed by our next stop in the Umbria region - Cortona, and staying in Bevagna. Of course, we cannot forget our inspirational visit to Assisi with a private guide. Everything was perfectly orchestrated by our agent. The train, the car, the hotels, the private tour guides, the tickets, were all taken care of. She also provided her emergency number should there have been any problem at all.We are so happy we chose this wonderful travel agency and, we must say, most dedicated and pleasant agent, to handle this dream vacation for us. One which we will remember forever!!Thank you – BRAVO!!!
Sincerely,
Veronica and Leonard B
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