Tuscany Food & Wine Tour

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 pick up 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.)

Related blog posts:

• Extend Your Stay: What To Do In Italy
• 5 Myths About Wine Tours And Why They Are Wrong
• The Simple Pleasure of a Tuscan Gastronomical Adventure: Cortona, Italy

Tour Details

• Private Tour: Choose your own dates
• Trip Price Per Person: $5,350
• Single supplement: $700
• Minimum: 6 people
• Guide: Giovanni Ramaccioni or other Tuscany-based guide
• Meals: All meals included except two lunches and two dinner
• General Tour FAQs

Private Tour Bookings

• Private Tours are available to book with your own group on any date you choose, given guide and lodging availability
• Please note –  Our pricing is based on double occupancy lodging. If upon finalizing your private trip, your group has a solo traveler in a room without a roommate, the single supplement becomes mandatory. This amount will differ depending on the itinerary. Please contact our tour operations team for specifics
• Customizations to the itinerary are possible with additional per person fees

Day 1

We meet in Florence after breakfast at 9:00 AM for short introductions. We will then load up the bus and depart for 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.

Next on our agenda is the winery Guicciardini Strozzi for a tasting with wine made from grapes harvested by hand and carefully selected, fermented in cement vats and steel autoclaves at controlled temperatures. After, we check into our charming historic villa out in the countryside and enjoy a delicious dinner of local fare.

Day 2

After breakfast, we’ll head out to Radda in Chianti for a historical visit. The mediaeval hilltop town has a long history with archeologists discovering traces dating back to 2000 BC. From there we’ll discover the wine of the area starting with Albola Winery. A castle among 900 hectares producing prestigious wines pasted down from generation to generation for close to 50 years.

Next up is the town of Castellina, a lively little village, full of restaurants and small shops. You will have time for exploration by foot and lunch on your own. The town is renowned for its exquisite wineries so we highly recommend a glass with lunch!

After we’ll head back to our wonderful villa in Chianti to relax by the pool, catch the sunset or enjoy an aperitif before dinner on the grounds together.

Day 3

After breakfast, we check out of our hotel and drive to Arezzo. The morning is yours to explore this charming Tuscan gem renowned for its beautifully preserved medieval architecture. The town’s vibrant Piazza Grande, with its sloping cobblestones and historical buildings is a must see for it’s unique antique fair and medieval vibes.

Our next stop is Gratena Winery for a private tour, tasting and light lunch. This winery is special because of their use of only native grape varieties, both Sangiovese and their exclusive GRATENA NERO grape which became an official Tuscan grape variety in 2010.

Once we’re full of food, wine and knowledge we jump back into our vehicle and transfer to our home for the next two nights in Cortona, made famous by the book Under the Tuscan Sun. We’ll check into our hotel and settle in before a local gelato tasting. Dinner will be together at a neighborhood trattoria.

Day 4

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 family run farm, Podere il Casale, 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, you’ll have free time to relax after a full day and find dinner on your own at one of the many incredible local establishments.

Day 5

After breakfast we’ll make out way to Citerna for a truffle hunting adventure. We will join a local truffle hunter and his trusted dog in a search for truffles, which can be found in this area at any time of the year.

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 take a short drive to Malvarina Agriturismo for a fun hands-on cooking class in a beautiful family-run stone farmhouse.

Our last stop of the day is our final hotel of the trip in Assisi. We’ll settle in, freshen up and and depart for dinner together at a local gem where we’ll try to outdo our previous successes with Tuscan cuisine.

Day 6

Try to save a little room during breakfast because are first stop is to an olive oil mill for a tasting in the ancient town of Spello, officially named one of “The Most Beautiful Villages of Italy.” Our visit will include a walk about the facility and learn the beautiful process of green liquid gold and pour some of their delicious olive oil varieties for a sample.

After, we’ll transfer to the central part of the Italian province of Perugia for an exploration of Bevagna. Its cobblestone streets are perfect for wandering, leading to artisan workshops where travelers can see traditional crafts like paper-making. Lunch will be on your own here.

We’ll cap the day off at Cantine Caprai who have been producing wine in the Montefalco DOCG since 1971. The tasting will include wine from their native unique Sagrantino vine. Sagrantino has an intimate structure whose secret lies in the type and concentration of tannin, which gives it a charismatic flavor. For this reason its grapes are used pure to produce the famous Montefalco Sagrantino DOCG.

Back in Assisi will be the location of our final farewell dinner. We’ll cheers to a once-in-a-lifetime trip with old or new friends and all the terrific memories we will bring home!

Day 7

You’ll enjoy a morning of breakfast at your leisure before checking out and starting your journey back home or shuttle onwards to Florence or Rome. (Check out Extend Your Stay: What To Do in Italy).

Book Now

Night 1 & 2: Villa Lecchi, Chianti: A charming historic villa out in the countryside surrounded by vineyards, olive groves, and cypress trees, overlooking the beautiful Elsa Valley.

Nights 3 & 4: Hotel San Michele, Cortona: Enjoy modern comforts in an ancient 15th-century palace, located in the historic center of Cortona. You’ll not only find beautifully and uniquely decorated rooms but incredible ancient artwork in the lobby.

Nights 5 & 6: Assisi. Check into the heart of Assisi, a hill town in central Italy’s Umbria region with fantastic views overlooking the countryside. Wander the charming streets and embrace the historic city.