Tuscany Wine Tour Itinerary

7 Days | 6 Nights

Start and Finish: Florence | vicinity of the Santa Maria Novella Train Station

(Please note: this is a sample itinerary. Each tour is unique.)


Day One

We’ll meet in Fiesole at a charming country hotel and board our spacious van and heading out to Montepulciano, one of Tuscany's breathtaking hill towns. Here we'll make two stops at artisanal wineries that produce the famed Vino Nobile di Montepulciano, and have a wander up the winding Medieval streets of the city center. Lunch will be a light spread at one of the wineries. After checking in at our villa in the lovely Valley d'Orcia, we'll head out to dinner in the Renaissance town of Pienza, where we will be greeted by a feast based on pecorino cheese and other local specialties.

Day Two

Our second day begins with a visit to the enchanting Abbey of Saint Antimo, a former Benedictine monastery built 900 years ago. We'll then have a tour and tasting at a small, historical Brunello di Montalcino-producing winery. After having lunch in the town of Montalcino, we'll head to one of our other favorite family-run wineries in the area that also makes a phenomenal extra virgin olive oil before returning to the hotel. Dinner will be in a very special nearby town that could easily be the setting for a fairytale.

Day Three

Today is dedicated to the Medieval town of Siena. We'll drop our bags off at our conveniently-located hotel and then have a guided tour of the city center followed by lunch in a traditional trattoria that serves  Sienese specialties, such as ribollita (a Tuscan bean soup), pici al cinghiale (thick, homemade spaghetti with wild boar ragu) and of course a glass or two of the local wine. The afternoon is yours to explore the city. Dinner will be on your own. (You will be provided with some of my favorites).


This morning we'll drive to a nearby bite-size hill town, Monteriggioni, and walk along Via Francigena, the ancient pilgrimage route leading to Rome. We’ll enjoy a hearty and well-deserved lunch at a local osteria. We’ll next head to San Gimignano, an elegant Tuscan hill town prized for its Vernaccia di San Gimignano, which is a deliciously floral and fresh white wine. After a tasting at one of the best wineries in the area, we'll head to the historic city center with some time to walk around and see the sights. Dinner will be at a lovely trattoria in the main square, where our senses will be awed by concoctions of local ingredients such as saffron, honey and various pecorino cheeses.


Welcome to the heart of Chianti Classico! For the next two days, we will be the guests of some spectacular Chianti producers spread out in the four main communes: Greve, Radda, Gaiole and Castellina. Today, we'll explore the later three with lunch at one of the wineries. After checking into our lovely Tuscan farmhouse, we'll be wined and dined at a local fave.


Today, we'll take it easy. We'll have a leisurely breakfast and morning by the pool or walking the hillside vineyards. A light lunch will be served as we do a tasting at our agriturismo, which also doubles as a fantastic winery. After lunch, we will have a cooking class, making Tuscan bread (no salt) and a variety of other dishes for our last dinner together.


This morning, we make our way back to the Santa Maria Novella Train Station in Florence and say our fond farewells. Typically, we are back in Florence around lunchtime.

Other Tuscany Wine + Culture Tour Possibilities: Truffle Hunting, Thermal Springs, Classical Music Concerts, Olive Harvesting...the Tuscan sky is the limit!