CUSTOM WINE TOUR
Tour Tuscany’s Chianti, Montepulciano, Montalcino wine zones
- Private sit-down tastings at Castello di Brolio, Ciacci Piccolomini d’Aragona, Poliziano & more
- Visit the medieval abbey of Sant’ Antimo
- Explore the Gothic city of Siena and its art treasures
- Taste pecorino cheese in the Renaissance town of Pienza
- Roll up your sleeves for a cooking lesson at a Chianti farmhouse
DAY 1 – PECORINO & THE NOBLE WINE OF MONTEPULCIANO
Welcome to our Tuscan wine tour! After a 9:30 a.m. pick-up in Florence, we shuttle to to the Renaissance city of Montepulciano in southern Tuscany (1-1/2 hours). A summer retreat for Florentine aristocrats, Montepulciano has palazzi and piazze embellished by Florence’s leading 15th C. architects. Wine took center stage in the 1700s, when its popularity among nobles and literati (like Voltaire) earned it the moniker Vino Nobile di Montepulciano.
Our first tasting is at Poliziano, one of Montepulciano's leading wineries and one of the first to heavily reinvest in the area and its wine, beginning in the 1960s. Afterwards we head into town for a welcome lunch at one of the most historic wineries, Gattavecchi. We'll eat in their medieval cantina (which also holds an Etruscan tomb), tasting their classic Vino Nobiles with lunch.
Afternoon takes us to another gem of the Renaissance, Pienza. The ability to make pecorino cheese was once considered so valuable a skill that women could list it on their dowry. We'll taste three types of pecorino in this cheese capital and see how aging cheese in walnut leaves, olive paste, hay, even grape must affects its flavor. Pienza is also famous for its architecture, being an “ideal” city commissioned by the Renaissance Pope Pius II. We’ll tour the Piccolomini Palace, stroll through its beautiful light-filled church, and learn a bit about Renaissance architectural theory and Leonardo’s Vitruvian Man.
Then we continue to our hotel in Montalcino. Our welcome dinner features Brunello-worthy Tuscan fare, such as gnocchi with wild herbs or beef braised in Brunello.
L, D • Hotel Dei Capitani
DAY 2 – EXPLORING BRUNELLO DI MONTALCINO
Today we dedicate to Brunello di Montalcino, Tuscany’s most prestigious wine. Brunello is made from sangiovese, a site-sensitive grape, so we’ll visit wineries on the north and south sides of Montalcino to let you compare Brunellos made in different microclimates. First is Donatella Cinelli Colombini (aka Casato Prime Donne) on the cooler northern fringe of the DOCG zone, which is run by an all-female staff. Our hostess will provide an entertaining history of Montalcino as we tour the cellars.
After lunch in Montalcino, we move 10 km south and get into a contemplate mood at the Abbey of Sant’ Antimo. Still today, friars live at this abbey founded by Charlemagne.
Then it’s on to our second Brunello tasting at Ciacci Piccolomini d’Aragona, a southside estate with great wines—and a great Cinderella story to match. Dinner is on your own in Montalcino. We'll point you to a lively, family-run trattoria that offers excellent pinci pasta and succulent veal glazed with balsamic-juniper sauce.
B • Hotel Dei Capitani
DAY 3 – THE GOTHIC CITY OF SIENA
Before transferring from Montalcino to the Chianti Classico zone, we'll have one final Brunello tasting, at either Caparzo or Altesino. (Parting from Brunello is such sweet sorrow!)
Then we stop in Siena for the day. We start with Nannini, a famous old coffee bar where we’ll sample panforte, a cake dense with nuts, candied fruits, and spices. After refueling on this medieval snack, we’ll be primed and ready to visit the Palazzo Pubblico, a splendid town hall lined with Italian Gothic frescoes. We’ll pay homage to the most famous: Simone Martini’s Maesta and Ambrogio Lorenzetti’s Good & Bad Government. Then we’ll circle by the striped Duomo, home to artworks by Michelangelo and Pinturicchio, for an optional visit.
Free time for lunch, shopping, and museum-going follows. Wine lovers can use this time to visit the Enoteca Nazionale, Italy’s national wine bar/showcase, housed in a Medici fortress. Mid-afternoon we’ll continue north to our second hotel, a renovated farmstead outside the medieval town of Radda in Chianti. Dinner will feature more scrumptious Tuscan cuisine.
B, D • Hotel Radda
DAY 4 – RICASOLI & THE BIRTH OF CHIANTI
America had Thomas Jefferson. Italy had multiple politicians with close ties to viticulture. In Tuscany, the most important was Bettino “Iron Baron” Ricasoli, Italy’s second Prime Minister and inventor of Chianti wine. We’ll visit Castello di Brolio, where the Ricasolis have been making wine since the 1100s. Walking through the magnificent gardens and on the castle’s crenulated walls, we’ll hear about the Iron Baron’s winemaking—and the legend of his ghost. Then we’ll taste their highly regarded Chiantis and Super Tuscan, and continue sampling over lunch at the winery’s Osteria del Castello.
The afternoon is devoted to the Baron’s cousin at Rocca di Montegrossi. Here Marco Ricasoli-Firidolfi diligently handcrafts some of the most elegant, refined Chiantis you’ll ever find.
Dinner is in a tiny hamlet called Volpaia, meaning “place of foxes.” Here we’ll have family-style servings of homemade pasta, wild boar stew, and fabulous torta della nonna (cream tort with pinenuts).
B, D • Hotel Radda
DAY 5 – CHIANTI CLASSICO & THE BLACK ROOSTER
Today's first winery is a gorgeous old property, the family-run Vecchie Terre di Montefili. Here we'll hear the legend of the black rooster as well as the history of this particular estate, once tended to by medieval monks.
Lunch follows in Greve in Chianti, birthplace of the explorer Verrazzano, and, if time allows, a visit to the Greve Enoteca, where 200+ wines are available to taste.
We'll follow that with a quick afternoon tasting at Fontodi, Caparsa, or Castello di Radda before rolling up our sleeves for a hands-on cooking lesson at a Chianti farmhouse. We'll dine on our brilliant labors and toast new friends with a glass of vin santo, the golden dessert wine—served, naturally, with almond biscotti.
B, D • Hotel Radda
DAY 6 – BUON VIAGGIO!
A shuttle to Florence, arriving by noon, and assistance with your travel plans. B
Florence or Pisa (continental), or Rome (intercontinental nonstop). To land in Florence or Pisa, you’ll need to connect somewhere in Europe. From the Florence airport to the city center, it’s a 20-minute taxi ride. If arriving in Pisa, the airport has its own train stop and is only an hour from Florence. Rome is the closest intercontinental airport, with direct flights to the US. If arriving in Rome, you’ll need to take a train from the airport to town (30 min.). Then from Rome’s main train station, it’s only 95 minutes to Florence on the fast train (EuroStar); the latter requires reservations.
Italian train schedule
Here's the English-language version of TrenItalia. Be aware that the schedule is posted only several months in advance, so if you're looking for long-range dates, try something sooner, just to get an idea of departure frequency and trip length.
Plan to land in Italy at least a day before the tour begins; that’s necessary to be at our starting point on time. Most people spend the preceding night in Florence. For hotel suggestions, email us or consult a good hotel search engine, such as TripAdvisor or Venere. If you’re spending just one night, we recommend staying near the main train station, Stazione Santa Maria Novella, since that is our meeting point. Otherwise, take your pick of neighborhoods. Florence is not a huge city, and it’s very walkable. In fact, we encourage you to get out and walk around; the streets are a living museum!
Our meeting point is Florence, at the main train station, Santa Maria Novella (details will be indicated in your information packet). From here, we shuttle to Chianti (about 1 hour), where the tour gets underway. (We cannot pick up from individual hotels because only taxis and permanent residents are allowed in Florence's city center.)
On our final day, we’ll have you back at the Florence train station by noon.
Because Tuscan Wine Treasures does not include any time in Florence, we recommend spending a few days in this fabulous art city, either before or after our tour. Florence is easy to navigate on your own. But there are also excellent thematic walking tours offered by our friends at ContextTravel. If you’d like to explore other small-sized cities in Tuscany, Florence is well connected with Lucca (1 hr, 20 min) and Arezzo (1 hr) by train. And it’s just a hop and a skip to Rome on the EuroStar express train (1 hr 35 min).
This is recommended to protect you from needless loss caused by last-minute cancellations, lost luggage, and more. Three sources are Travelex Insurance, (800) 228-9792; CSA Travel Protection, (800) 348-9505; and Travel Guard, (800) 826-1300.
When packing, check www.weather.com. Go to “Radda in Chianti, Italy” and “Montalcino, Italy” to get a general idea of temperatures and forecast.
For cancellation policy & more, see our General Information page.
For private, custom groups only
Minimum group size: 2
Contact us to pick dates
Single supplement: $350
Price based on this 6-day itinerary for 2 pax; discounts for larger groups. Modifications are possible, including the number of days, level of accommodations, amount of wine tastings, and inclusion of meals.
Meet & Depart
Florence train station
- 5 nights accommodations (double room) in 4-star hotel (Chianti) and 3-star (Montalcino) hotels, with breakfast buffet
- 3 gourmet dinners (three courses with wine)
- 1 hands-on cooking lesson, with dinner & wine included
- 1 welcome lunch
- All wine tastings mentioned
- Admission to Castello di Brolio
- Shuttle at beginning/end of tour, as described
What's not included
- Air travel
- 1 dinner on your own & most lunches
- After-dinner drinks, or special wines at tastings that are not part of what is provided to the group
- Items of a personal nature
- Anything not specified as included