Public Tuscany Food, Wine & Culture 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 trees and crossed with the famous strada bianchi or white-colored dirt roads.

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: September  4 – 10, 2026
• Trip Price Per Person: $5,400
• Single supplement: $700
• Group Size: 10 – 18 people
• Guide: Giovanni Ramaccioni or other Tuscany-based guide
• 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 9:30 AM for short introductions. We will depart via foot for a morning walk around the Sant’Ambrogio markets. We will meet local growers and sample some of their farm-to-table products, taste artisanal cheeses made with truffle & goat milk and sample ‘drunk cheese’ made with Barolo Wine. We’ll stop at Fabio Picchi’s organic food store, CBIO, and end with something sweet at the rooftop garden nursery.

With happy bellies, we hop on a private bus and transfer to Poggibonsi for a tasting at Winery Guicciardini Strozzi, where wine is made from hand-harvested, carefully selected grapes, 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.

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 medieval hilltop town has a long history, with archaeologists discovering traces dating back to 2000 BC. From there, we’ll discover the wines of the area, starting with Castello di Volpaia, which has a history dating back to 1172.

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, and enjoy a hands-on pizza cooking class together right at our hotel!

Day 3

After breakfast, we check out of our hotel and drive to Arezzo, a 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. Lucky for us, it’s the first Sunday of the month, which means we will explore the famous Arezzo Antiques Fair, featuring over 500 exhibitors selling a vast range of antiques. After, you’ll have time to explore on your own and have lunch.

No need for a sweet treat on your own after lunch, we will do that together! Our next stop is a chocolate and gelato tasting at Vestri.

Once we’re full of food, sweets 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. 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 DE’ Ricci for a tasting and tour of the Cathedral, which is like a time capsule; this is where the Ricci family started to make wine back in 1337. 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.

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. You’ll then have free time on your own to explore Spello and have lunch.

We’ll cap the day off the day with a short drive to Malvarina Agriturismo for a fun hands-on cooking class in a beautiful family-run stone farmhouse. 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 and an optional walk to the Sanctuary of Eremo delle Carceri 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: Hotel Ideale, 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.