Most culinary tours rush you from place to place in groups so big you barely hear your guide, let alone savor the moment. Tuscany — one of the most romantic, delicious, and storied regions on earth — deserves more than a crowded bus and a hurried tasting.
Travelers tell us again and again: They want something smaller. Slower. More personal. A trip where they can actually taste Tuscany — not just observe it.
This special extra-small group departure—limited to just 8 guests—was designed exactly for that.
With fewer people, everything opens up:
More time with your guide…Who becomes a true host rather than a microphone in the distance.
Easier access to local…Artisans, vintners, truffle hunters, and chefs who welcome small groups with genuine warmth.
A close-knit, relaxed feel…Where conversations linger, friendships form naturally, and every experience feels tailored to you.
And what experiences they are…
You’ll begin in Florence—the cradle of the Renaissance—before drifting through the iconic rolling hills of Tuscany and into the quieter charms of Umbria.
Every moment is unhurried. Every tasting feels like it was meant just for your group. Every day brings a blend of history, flavor, and connection — the kind of magic that only happens when you’re traveling intimately and intentionally.
Tuscany is spectacular no matter how you see it…but Tuscany in a group of eight feels like it was crafted just for you.
(And yes — we can accommodate nearly all dietary needs so every traveler feels welcomed at the table.)
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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.
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.
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.
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.
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.
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!
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).
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.
Not Included: Travel to and from destination, wine with meals, personal expenses, and optional gratuities to local staff and your guide. 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.
We meet in the morning on the first day of the tour in Florence. We highly recommend you arrive at least one day in advance. The tour finishes in Assisi after breakfast on the final day of the tour. Assisi is on the 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.
