Tuscany is one of the great destinations of Italy and, indeed, of the entire world. The beautiful scenery comes from the large tracts of agricultural land placed on rolling hills, dotted with cypress tress and crossed with the famous strada bianchi or white-colored dirt roads.

It is hard to say whether Tuscany is better known for its food or its wine and this toss-up is what makes this region perfect for a combination Food & Wine Vacation.

We start our tour in Florence, capital of the Medici, and hit major areas including Chianti, Arezzo, Assisi, and Montepulciano, with a side trip into Umbria. Our days are filled with wine tastings, visits to local food producers and sellers, and even truffle hunting in the forests visited by few tourists.

Tuscany is a spectacular region for a vacation and there is no better way to visit than to focus on the local food and wine. (Note: We can cater to almost any food allergy or eating preference on this and all our tours.)

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Unique Experiences

  • Join our small group public tour or create your own private group
  • Engage in truffle hunting and a cooking class with famous agriculturist Augusto Verando Tocci
  • Tour a local pecorino (sheep’s cheese) farm in Pienza followed by a picnic
  • Meet with a famous butcher to hear about the many types of meat in the Tuscan diet
  • Learn about coffee roasting and barista training at a cafe in Arezzo
  • Take part in a gelato making demonstration at Gelateria Ghignoni
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Tour Details

Tour Details

  • Location: Tuscany
  • Next Public Tour Date: September 3 – 9, 2017
  • Trip Price Per Person: $3,500
  • Optional single supplement: $900
  • Host: likely to be Giovanni Ramaccioni or Giacomo Benedetti
  • Meals: All meals included except one lunch
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Private Tour Option

  • Private Tours are available to book with your own group on any date you choose, given lodging availability, as either Classic or Deluxe
  • Deluxe  Tour: $4,900 per person (optional $1,400 single suppl.)
  • Classic  Tour: $3,500 per person (optional $900 single suppl.)
  • Minimum: 4 people
  • Customizations to the above itinerary possible with additional fees 

The following is included in our Deluxe Tour offering:

  • Professionally selected wines with dinner
  • Upgraded to luxury accommodations
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Tour Itinerary

Day 1


We meet at our Florence hotel at 1:30 PM and set off on an exploratory walk of the city, focusing on its history and culture through the eyes of a food lover. (If you wish to visit the David or any of the other impressive historical sites, plan on arriving to Florence a day early.) Your guide is a wealth of knowledge about all things Tuscany – food, wine, history, and culture. In the late afternoon, we’ll stop at B.Gallo, a “lounge aperitif” where we’ll toast the waning day with a Prosecco, the famous Italian sparkling white wine.

We end up at the Mercato Centrale, a building dating from 1874 that hosts food stalls featuring everything Tuscan: butchers selling pigs feet, chickens, and sausages; specialty cheese, olives, pasta, and bread vendors; seafood; and a wide variety of fruits and vegetables, nuts and spices. The market recently renovated the top floor to create a dining experience where we will visit various restaurants, order a variety of dishes, and eat a family-style, casual meal that is an excellent introduction to the Tuscan cuisine – all washed down with a bottle of Brunello or Vino Nobile di Montepulciano wine.

After dinner we head back to the hotel and rest up for tomorrow’s adventures – our first full food and wine day in Tuscany.

Day 2

San Gimignano Italy Tuscany

We check out of our hotel and head to one of the most famous wine regions with one of the most famous wine styles in Italy: Chianti.

Our first stop is the picturesque city of San Gimignano, a small medieval walled town famous for its dozen or so towers sticking up into the sky. After exploring the town on foot, we’ll head to the local Fattoria Poggio Alloro for a lunch of food products from this farm, such as the Chianina brand of beef and the saffron spice which has been locally grown since the 13th century, paired with the white wine Vernacciadi, also grown on site.

After lunch, we’ll transfer to the small town of Greve where we’ll take a brief walk to visit the famous butcher Dario Cecchini of Macelleria Cecchini, where we will learn all about the many types of meat in the Tuscan diet.

Next on our agenda is the winery Castello di Volpaia, where we’ll do a tasting of the famous Chianti Classico wine. We finally head to our hotel for the night, Dievole, an exquisite country retreat on 1000 acres with vineyards that were planted over 900 years ago! We’ll visit their cellars and then eat dinner outside in the garden if the weather is good, with wines from the estate paired to our courses.

Day 3


We drive in the morning to Arezzo to visit the Piazza Grande and stop at Caffé River, one of the eight or nine coffee roasters in the city that supply the city’s many bars with espresso and other coffee drinks. We’ll learn about the roasting process and their barista training school. We then jump back in our vehicle to visit nearby Vestri Cioccolato, a chocolate maker that has been producing delicious chocolate for 30 years and which owns its own farm in the Dominican Republic.

Next, we head to the beautiful small town of Anghiari, perched high on a hillside. We’ll visit an Agriturismo (a farm that now engages in tourism), Valle di Mezzo, where we’ll have a lunch featuring products from the farm. We’ll dine with the president of the local La Strada dei Sapori, “The Road of Taste” which is sort of like a Wine Trail but featuring local agricultural producers.

After lunch, we’ll take a break from our food and wine tasting to visit the world-famous Busatti linen factory, sold in such outlets as William & Sonoma. This family-run business has been based in Anghiari since 1842. The factory tour is extremely interesting and you can purchase products to take home.

We head to the walled town of Sansepolcro to check into our hotel for an hour’s rest and then visit a local hotspot, Enoteca Guidi, which is a combination wine bar and restaurant that serves outstanding local cuisine in a casual setting.

Day 4


Most tourists don’t make it to the section of Tuscany called the Upper Tiber Valley. Even fewer travel to the hamlet of Badia Tedalda, 40 minutes up into the Apennine Mountains. But it is here we will travel this morning, specifically to visit Augusto Verando Tocci, a botanist famous for his pursuit of the equally famous truffle.

Verando will take us into the forest with his trusted dog to look for truffles, which can be found in this area at any time of the year. Successful or not, we will return to his home to participate in a cooking class and lunch involving many of the edible plants and roots found in the forest, including the local liquor Spinello.

After lunch, we’ll return to Sansepolcro for a visit to Gelateria Ghignoni, where we’ll meet owner Palmiro Bruschi who will demonstrate how he makes gelato while giving us a history of the product, from its origins in Sicily to the key contribution of Catherine Medici. Many gelato stores in Italy do not make their own product but purchase it from a big manufacturer, so this will be a special visit.

Our dinner tonight is at Relais Palazzo di Luglio, situated on 30 acres in the countryside outside Sansepolcro. The owner Giuliano previously owned one of the most successful restaurants in town and produces an elegant, traditional Tuscan dinner featuring whatever is in season.

Day 5

Tuscany Grapes

Yes, this is a food and wine tour of Tuscany but nearby Umbria is well worth a visit. We’ll start out with a visit to the very small and local olive oil mill of Emanuele Ragani and his family. Emanuele will not only show us how the mill, with an actual grist stone, operates but will fire up a wood oven, heat up bread, and pour delicious olive oil on top for a tasting.

We then head to Assisi, the city made famous by St. Francis, for a tour of the city and the church where he is buried. Assisi is a great town to walk around on your own, with many shops and restaurants, and we are on our own here for lunch. After lunch, we’ll head to Arnaldo Caprai winery, a leading producer of the wine Sagrantino di Montefalco. If you have never had Umbrian wine before, you will be impressed.

After our wine tasting, our time in Umbria is ended and it is back to Tuscany as we drive to Cortona, featured in the book Under the Tuscan Sun and our home for the evening. We’ll check into our hotel and then walk to dinner at La Bucaccia, where they serve a variety of local dishes such as, wild boar ragu with tagliatelle, pici with tomato sauce, pecorino flan, seasonal vegetable soup, and fresh bruschetta.

Day 6


The Val d’Orcia is one of the most beautiful sections of Tuscany, which is one of the most beautiful provinces of Italy, which is one of the most beautiful countries in the world. We are in a good place!

We’ll start our tour by visiting the city of Pienza, perched high above the valley and designated a UNESCO World Heritage Site. (The entire valley is designated a World Cultural Landscape.) After a quick historical walking tour of the city, we’ll head to a local farm that specializes in making pecorino, the ubiquitous local sheep’s cheese. We’ll learn about the process, have a taste of the fresh cheese, and eat a nice picnic lunch right on the farm.

It is then on to Montepulciano, another famous hilltop town, where you will have an hour to wander the streets on your own. We then gather together again to visit Cantine Gattavecchi for a tour of their barrel room and tasting of the local wine, the outstanding Vino Nobile di Montepulciano. Heading back to Cortona, we’ll share a final meal together at the Locanda al Pozzo Antico, a fine dining establishment run by the owner Paola where we’ll try to outdo our previous successes with Tuscan cuisine.

Day 7

Cortona, Tuscany, Italy

We’ll take a post-breakfast walk of Cortona, pointing out some of the important sites that featured in Under the Tuscan Sun. You are then free to take the train or a shuttle onwards to Florence or Rome. Or perhaps you’ll follow the theme of the book and decide to stay in Tuscany?

"What a fantastic trip we had in Tuscany! I can't thank you and Giovanni enough for your kindness, flexibility and support. It makes for a more relaxing and enjoyable experience. "

− Dane M.

"As is with every Taste Vacation tour, the attention to detail is incredible. Everything from ensuring that participants have enough wine, tasting spectacular wines, visiting exclusive wineries, dining on great food, touring beautiful vineyards, plenty of activities to keep us busy, and enjoying unique restaurants is covered."

− Elizabeth & Jake

"I was concerned about the limitations of being on a guided tour as well as having to spend the entire time with a group of strangers. What I found was that the tours were extremely well planned and the accommodations, meals, wine tastings, and activities were perfect! And at the end of the trip, the people that began the tour not knowing each other, parted as a group of forever friends planning another adventure together with Taste

− Alice T.

Tour Accommodations


Night 1: Antica Torre di Via Tornabuoni, Florence: An incredible hotel located in a tower built in the first half of the 13th century and situated in the center of the city.

Night 2: Dievole, Chianti: An exquisite country retreat on 1,000 acres with vineyards that were planted as early as 1090 – over 900 years ago!

Nights 3 &4: Palazzo Magi, Sansepolcro: Located in a 14th century residence within the walled town of Sansepolcro, one of our favorite Tuscan towns and rarely visited by tourists.

Nights 5 & 6: Villa Marsili, Cortona: Luxury hotel located in the center of Cortona, which sits high on a hill overlooking the Val die Chiana in central Tuscany.

Accommodation upgrades are available upon request.

Please note: Hotels are subject to availability.  If listed hotel is not available at time of tour, a hotel that is equal or better to the original will be secured.

What is Included

  • All Local Transportation
  • Double Occupancy Lodging
  • All Meals Except One Lunch
  • All Scheduled Activities
  • Wine During Organized Tastings
  • Wines Included With Meals on Deluxe Private Tours
  • Professional Tour Host

Not Included: Travel to and from destination, wine with meals (included on Deluxe Private Tours), personal expenses, and optional gratuities to local staff and your Host. Travel insurance is also not included, though we highly recommend it.  Check out our Travel Insurance page for more information.

While the general trip itinerary will remain the same, the actual restaurants, hotels, and activities listed are subject to modifications. Changes that are out of our control are common — restaurants close or lose their amazing chef, a winery changes their visiting hours, a hotel gets remodeled, etc. You are entrusting us to create an outstanding vacation for you and so it is possible we may take the liberty of making necessary changes to the itinerary that will improve your overall trip experience. If there is any one experience that is going to make or break your trip, please discuss this with us in advance.

Arrival & Departure

We meet at 1:30 PM on the first day of the tour at our downtown Florence hotel, allowing you to arrive either that morning or the day before. The tour finishes in Cortona before lunch on the final day of the tour. Cortona is on the mail rail line connecting Florence to Rome, so you can fly out of either city. One nice option is to fly into Florence and out of Rome, so you can visit both cities.