Quintessential 10-Day Tuscany Food and Wine Tour

Vineyard and winery in the Chianti region of Tuscany, Italy

What to expect on this itinerary

During this 10-day Tuscany wine and food tour, indulge in the grandeur of rustic cuisine and develop an intimate understanding of the gorgeous landscape. Your private tours led by specialist guides offer insight into the heritage of local flavors. This customizable tour will shine a brighter light on Tuscany’s culinary marvels, such as visiting renowned winemaking regions, basking in the enticing aromas of a private kitchen, and scouring woodlands for the elusive white truffle.

Countries Visited

Italy

Places Visited

Florence, Siena, Chianti Region, Val d’Orcia, Pienza, Bolgheri

Suggested Duration

10 Days

Customizable Itinerary

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Day 1

Florence – Introductory Dinner

Florence is a fascinating city of art, fashion, tradition, and gastronomy. Here, elegant palaces line cobbled lanes, and the aroma of freshly brewed espresso lingers among the scattered bakeries. Your flight will land at Florence Peretola Airport, where your private transfer will greet you upon your arrival and escort you into the heart of the city. After settling in to the comforts of your luxurious accommodation, your guide will introduce you to the marvels of Florence. First, you will explore the bustling neighborhood of San Lorenzo. Eventually, you will step into the majestic display of architecture in the San Lorenzo Church.

What's Included:

Accommodation
Transfer
Day 2

Florence – Private Cooking Class

Day 3

Florence – Gelato Tour of Florence

Day 4

Chianti – Chianti Wine Excursion

Day 5

Chianti – Winemaking in Chianti

Day 6

Chianti – Sample Cheeses and Wines

Day 7

Siena – Walking Tour and Enoteca Visit

Day 8

Siena – Bolgheri Wine Tour

Day 9

Siena – Private Truffle Hunt

Day 10

Siena – Departure

Trip Highlights

  • Craft your own wine in the cellar of a private vineyard under the guidance of a working oenologist
  • Learn how to master the art of handmade pasta during a private cooking class with a celebrated Florentine chef
  • Delight in the flavors of Chianti Classico when visiting a celebrated winery near the antique walls of Radda in Chianti
  • Enjoy a private demonstration and workshop on the process of making pecorino cheese on a farm outside of Pienza
  • Bask in the charming ambiance of Bolgheri’s small streets and quiet artisan shops before visiting a celebrated vineyard to taste super Tuscans
  • Indulge in the robust and earthy characteristics of truffles during a lunch that focuses on the exceptional ingredient after a private truffle hunt
  • Witness Michelangelo’s marvelous sculptures, such as his imaginative and intricate depiction of the biblical warrior David, in the Galleria dell’Accademia
  • Embrace the diverse flavors of gelato in Florence during a private gelato tour

Detailed Description

Your 10-day food and wine tour of Tuscany will feature the luxurious landscape that is celebrated for its sprawling vineyards and country roads that are lined with cypress trees. Your specialist guides and private transfers will provide an immersive experience, during which you will delight in Italy’s authentic culture, continued traditions, and remarkable flavors. You will also discover how the gastronomy of Tuscany derives from centuries of gastronomic customs. Furthermore, you will gain insight into the history of the region and its connection to greater Italy while indulging in the unspoiled scenery and welcoming ambiance of medieval towns.

Your food and wine tour of Tuscany will begin with your arrival at Florence’s international airport, where you will meet your private transfer. You will have three nights in Florence, starting with an introductory dinner that will highlight the delicious flavors of Tuscan cuisine. A historically based tour of the city will present the layers of medieval and Renaissance history through the lens of art at the Uffizi Gallery. Afterward, you will partake in a private cooking class that will teach you how to perfect traditional handmade pasta. You will then continue to uncover the marvels of Florence with a visit to the Galleria dell’Accademia to view Michelangelo’s David before partaking in a fantastic gelato tour. This tour will provide you with a glimpse of the unique history and best artisanal flavors of the city.

Your three nights in Chianti will begin with visiting the medieval towns that produce the wines of the region, beginning with Radda in Chianti. You can sample a variety of wines in a historic wine bar known as an enoteca. You will have a special day at a local vineyard in Chianti, where you can produce your own bottle of wine under the guidance of a trained oenologist. In the town of Pienza, you can enjoy the Renaissance architecture and serene ambiance before learning about the local connection to pecorino cheese. Afterward, you will participate in a cheese demonstration, workshop, and sampling on a local farm.

You will then transfer to Siena for three nights. Here, you will discover the preserved medieval wonder of the city with a private walking tour of the historic streets and structures. You will also visit a historic enoteca for a sampling of the local wines. You will also have a half-day visit to the town of Bolgheri, which is a town that possesses the feeling of being discovered and surrounded by natural beauty. You will visit a nearby vineyard for a tasting of the specialty wines that are produced in the region, such as the famous Super Tuscans. Your final tour in Tuscany will take place in the woodlands outside of Siena. Here, you will search for truffles with a seasoned guide, which will result in a marvelous lunch that focuses on the robust flavors of truffles.

Starting Price

$3,600 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.

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Luxury Italy Group Tour Review: Rome, Tuscany, Chianti, Montepulciano, Montalcino, Siena, Florence, Pisa, Lucca, San Gimignano

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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Travel Review: Italy Birthday Vacation, Florence Cinque Terre, Siena, Tuscany, San Gimignano, Lucca, Sailing Pesto Making Class

The 2 weeks in Italy our travel agent planned for us  was fantastic. We has a fantastic schedule with experienced and excellent guides. This was my first time in Italy, a 60th birthday trip with my sisters, we have varied interests and she hit the mark on them all! The hotel location in Sestri Levante was the perfect location. The weather was beautiful for late Sept., we enjoyed the beach and calm Mediterranean waters when we were relaxing back at the hotel.  The guide on our hike in Cinque Terra was very good. We did not know what to expect. His knowledge on the history of the area kept us more than expected. The guide knew the area and was able to rearrange our schedule due to rough winds that cancelled the ferry.

I would have never taken a pesto making class, but it was a highlight!

The sailing day was absolutely perfect. The weather was beautiful, and the skipper was a true sailor!

On our way to Florence we stopped in Lucca and a winery that were fantastic. The driver was prompt and informative. Our hotel in Florence had the perfect location! Close to both sides of the river to explore by foot every day. The 2 days with our guide were fantastic! She was excellent in every way, she knew the history, art and even helped with restaurant suggestions and reservations. Having a guide was the perfect way to not only see the sights but understand the time period and history. The day trips out of Florence to Chianti, Siena and San Gimignano, were perfect with wine-tasting interspersed with visiting the smaller towns in the Tuscany region. The weather was beautiful both a weeks we were in Italy. 

The trip exceeded our expectations in every-way and we will all be repeat customers!! 

Thanks for making my 60th birthday trip, the trip of a lifetime!

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Review: Luxury Italian Vacation, Rome, Venice, Florence, Positano, Siena, Tuscany, Napoli, Amalfi Coast, Pompeii, Duomo, Colosseum

Our trip to Italy proved to be, indeed, 'fantastica'!  We traveled to Venice for 2 nights; by train to Florence for 2 nights where we stayed at the luxurious Palazzo Niccolini al Duomo; by train to Siena for 2 nights.  From there we speed-railed it by "TreniItalia" to Napoli where we were picked up in a private car to take us to the jaw dropping showcase Italian seacoast resort of Positano.  We stayed there for 3 glorious nights at the Covo dei Saraceni with the most breath taking views of the bay and the Amalfi Coast that you could ever see.  Finally, we were picked up in a private car and taken to Napoli for a train to Rome.  But first...we had a 2-hour stop with guided tour of Pompeii's ruins.  Finally, after training to Rome, we stayed at the quietly elegant Residenza di Ripetta hotel near the Piazza del Populo.

I've left out the most important parts which were the incredible tours that this Italy travel agency arranged for us.  We must've seen everything that this trip could offer.  And it was all done over two weeks.  We toured Venice during the calamitous weekend of George Clooney's wedding.  No, we couldn't go to the wedding but we had a fabulous time nonetheless!  Our agent and her team put us up at the quaint yet convenient Hotel Georgioni in Venice quite near the Rialto Bridge.  We had been picked up at the airport and water-taxied to our hotel.  During our fabulous 48-hour stay, we saw every nook and cranny of central Venice anchored by the eye-popping Piazza San Marco.  Included in our stay was a tour of the Doge's Palace with its art treasures galore and a tour of the markets area replete with a 30-minute gondola ride through a memory of photographs that I took that I will never forget.  The Rialto Bridge at night, along with the rest of Venice, is one of the most romantic sights in the world.  The lighting of this magnificent city at night is unforgettable.

From there it was on to the renaissance city and Medici capital of Florence to our luxurious hotel, the Palazzo Niccolini al Duomo right across the street from the magnificent Duomo itself.  We walked and toured everything; from the Accademia Gallery and the "David" masterpiece by Michelangelo to the Uffizzi Gallery and Vasari Corridor to the Ponte Vecchio where I bought my beautiful wife a golden ring the size of Sardinia.  We saw street musicians, vendors, activists and sellers of all kinds.  We even saw a Brahma bull towing a wagon hauling over a 1000 bottles of Chianti up the main street into the square.  The food? Indescribably memorable.  Just like all of Italy.  

On to Siena where the Medieval contrasts with the Renaissance of Florence beautifully.  These 2 cities, once rivals, are now bastions of art and relics dating back centuries...from every genius known to man.  Siena, with its massive "Campo" is the meeting point for all of Tuscany seemingly.  They run their horse race there every year around the Campo.  We didn't see it.  But we did see a huge nighttime sports car rally featuring the finest autos made by Ferrari, Maserati, Alfa-Romeo and others.

Taking the train in Italy is a far preferable way to travel than car.  We had the benefit of traveling in clean cars traveling almost 200 MPH in almost serene silence - with some of the greatest views ever.  It's fun...and grabbing a panini and a water is the perfect way to relax and have lunch aboard the train.  

Positano.  What can we say other than it was a 3-day dream.  Everything that you could possibly photograph is present in this sea coast paradise.  Staying at the singular Covo dei Saraceni provided us with a view out of our bedroom window that could stop time.  It was THAT beautiful!  The views of villas tucked into the mountains; the roads that snake their way down to the beach, the lovely little shops that adorn the narrow streets all make for fantastic photographs so compelling that friends would envy you and your experience.  From Positano, we took a day trip out to the Isle of Capri.  Capri, for us, was like Italy's Catalina Island - kinda honkytonk and overpriced yet still very fun.  Especially when you bus up to the top to take in the wildly sweeping and sometimes scary sights from Anacapri, the island's little town that's 'above it all.'  We toured the historic Villa San Michele with its stories of Axel Munthe, the one time owner and Renaissance man in his own right.

Finally, we finished with 3 days in exciting unstoppable "Roma".  Can there be any more excitement?  Any more history? Any more style?  We saw everything: the Colosseum, the Forum, the Pantheon, the Piazza Navone, the Carra Calla Baths, Circus Maximus, Palatine Hill, The Arch of Constantine, The Villas of Borghese.  We rowed boats, we road bicycle carts, we got lost.  Moreover, we ate gelato at the 150-flavors of Della Palma.  We heard stories about Roman Emperors and the various peccadilloes, their loves (and lovers!) and their battles.  Both won and lost.  

This whole trip will go down in our memory as arguably the greatest trip that we ever took.  We've been together almost 20 years and, thanks to our agent and her team at this travel company, we enjoyed our 2nd honeymoon to the max.  Not once in our 12-day itinerary did we have a hiccup.  Everything that our agency arranged for us from tours, to drivers to train departures and tickets etc went off without a hitch.  All the I's were dotted...all the t's were crossed.  I would recommend this travel agency as a 5-star travel agency to anyone who would ask.  I'd trust them completely.  Indeed, I have the pictures to last a lifetime.  I have memories that will last even longer.  

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Italy Anniversary Vacation Review: Florence, Tuscany, Cinque Terre, Pietrasanta, Cortona, Chianti, Siena, Wine & Cuisine, Culture

Our travel agency planned our wonderful trip to Tuscany, Cinque Terre and Florence. I had high expectations when I embarked on the trip and they were exceeded by the actual experience. Thank you for introducing us to Pietrasanta. What a wonderful small city! It was such a pleasure just walking the streets, having a drink in the square and taking in the local culture. The hotel that you booked for us there was terrific. Great location, beautiful rooms, exceptional service. The excursions to Cinque Terre, by sea and by land, were everything I had hoped for. Our next stop, Cortona, was beyond wonderful. The inn was one of the most romantic places that I’ve ever been. Perfect for our anniversary trip. And the food at their restaurant!! I’m still dreaming about it! The Wine and cheese excursion and cooking class that you planned for us there were so, so good. We ate very well in Cortona!  Our final stop, Florence, was equally terrific. Ideally located hotel, vibrant tour guide and another terrific excursion to Chianti and Siena. My only complaint was that it didn’t last longer .Their attention to detail really made this trip run smoothly. They really listened to what we wanted and planned the ideal trip for us. I look forward to planning my next vacation with this travel agency!!

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Review: Honeymoon in Italy, Rome, Venice, Florence, Tuscany, Siena, San Gimignano, Lucca, Sorrento, Pisa, Capri, Pompeii

When we inquired about a trip on Zicasso, they told us a few companies would reach out to us with different offers on our desired location. It only took one reply back from this agent for me to know that we would have a more personable experience with this travel agency. (Mainly because he was straight up with us concerning itinerary ideas, especially regarding weather and how it is unpredictable in March. He patiently worked with my fiance and me for quite a while before we approved the final itinerary filled with transportation to and from hotels, private tours (some meant to be small group, but we ended up being only ones), and pre-planned relaxing train-rides. There wasn’t a moment of our trip that we had to worry or even think about- really. Our first stop was Rome, where we spent 3 days. Upon arrival at the airport in Rome, we had a driver waiting for us, which was a huge relief since we were tired and last thing we wanted to stress about was how to get to our hotel. Our local point-of-contact for the agency also called once we arrived to make sure we had everything we needed. He was great! Once we reached our hotel, we slept off the jet-lag and then our holiday started. March is the early beginning of the tourist season, so we were able to do many things without waiting. Not saying it was empty, but we had room on the sidewalks and were in and out of restaurants in no time at all. I also highly recommend planning free days in each city, as you will want to look around for yourself and take your time in certain parts. Even if you spend a week in every city, you always leave feeling like you needed much more time, as there is so much to do and so little time in a day. We spent 3 days/4 nights in Florence. It was in Florence that we were able to easily tour a good bit of what Tuscany has to offer. Through tours our agent set up for us, we visited the beautiful cities of Siena, San Gimignano (Our Favorite), Lucca, Pisa, and the Chianti Region. We tasted sooooo many wonderful wines and privately ate at local restaurants for lunch. We also took a short train ride to Venice for a day trip, as I craved a gondola ride. Everything was planned so perfectly. The minute we stepped off the train in Venezia our guide to get us to our marked location was there with a water taxi to take us to St Mark’s Square. There, she directed us to our gondola and we spent the day wondering around Venice until meeting up back with her and the water taxi to take us back to the train station. After Florence, we traveled to Sorrento (our other favorite!) along the Amalfi Coast. It was magical and the weather was perfect. We had our own boat to visit the grottos (no wait for the Blue Grotto either!) and to the Isle of Capri; and although most of the shops were closed on the isle (early season still), it was beautiful and we were able to relax on the beach. We saw Pompeii and even hiked up Mount Vesuvius. Sorrento was a quaint and charming city and we made friends with quite a few locals. We truly had a wonderful honeymoon and I would recommend this agency to everyone. We could not be happier!

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Review: Luxury Italy Family Vacation, Rome, Venice, Florence, Tuscany, Chianti, Verona, Milan

My husband and I, along with our 2 children (age 20 and 17), enjoyed a wonderful Italian vacation booked through Zicasso and this travel agency.  Our travel consultants listened to my ideas and arranged for us a fantastic custom itinerary.   They stayed within the budget allotted, offered choices for beautiful hotels and private tours, and made several revisions as per our request.  We departed from New York on our 25th anniversary, and spent 10 days traveling the country within the month of November.  This off-season time proved to be a great decision as reservations were easy to obtain, crowds were minimal (mostly all locals), and the weather was conducive for walking and sightseeing (average 60 degrees F).  Transportation and the personal drivers were top notch; with Mercedes SUVs or minivans to take my family from Milan-Chianti-Florence-Verona-Venice and then the high speed train down to Rome.  Accommodations arranged for us were phenomenal!  We stayed in a 12th century castle in Chianti, in the heart of the city center in Florence, and near the Spanish Steps in Rome.  The personal tour guides were friendly and knowledgable, and were happy to recommend eateries preferred by locals.  All in all, everything was flawless. We plan to return some day to see the Amalfi coast, Positano and Capri.  We would absolutely recommend these travel consultants, and the travel company team to anyone who is looking for a personalized Italian vacation.

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

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