Spotlighting Brunello di Montalcino & Bolgheri’s Super Tuscans

  • Visit two wine zones of Tuscany: coastal Bolgheri, birthplace of Super Tuscans; and Brunello di Montalcino, the best of sangiovese
  • Enjoy private, sit-down tastings at Ornellaia, Biondi Santi, Casanova di Neri and more
  • Visit the medieval towns of Montalcino, Bolgheri, and Castagneto Carducci 
  • Explore food and wine pairings during nightly wine dinners


After a pick-up at the Pisa train station, we’ll shuttle down the coast to the Maremma, Tuscany’s Wild West. Our first stop is Castello del Terriccio, founded by a thoroughbred horse breeder (another business for which the Maremma is famous). Its vast property resembles the farms of yore more than any other winery on this tour, but their wines suit modern tastes, with mouth-watering Super Tuscan blends at various price points. 

Next is Ornellaia, founded by Ludovico Antinori. Visiting the vineyards, we’ll come to understand why the geography of Bolgheri is so well suited to cabernet sauvignon, cabernet franc, merlot, and syrah. And in the cellar, we’ll hear about a level of meticulous care that helps explain why Ornellaia has become such a prized cult wine.

Finally, we visit one of Bolgheri’s pioneers: Michele Satta, a mid-sized, family-owned winery founded in the 1980s. Here you’ll find both blended and pure sangiovese (including a fantastic rosé), plus an excellent example of vermentino, the heat-loving white grape of coastal Tuscany. After settling into our countryside hotel, we head to dinner in Castagneto Carducci, a medieval town tucked into the Apennine hills. Up in the mountains, the menu focuses on woodland cuisine, with wild boar (cinghiale) and polenta, a regional favorite.
D • Podere Conte Gherardo

Petra, the newest winery on this portion of the tour, is just outside the Bolgheri DOC zone. It’s an architecturally stunning cellar designed by Swiss architect Mario Botta and is indicative of the sizable new investments flowing into Tuscany’s youngest wine zone—and it makes stunning wine.

After the winery tour and lunch, we’ll visit another newish property on the main wine road of Bolgheri, Via Bolgherese: Poggio al Tesoro, founded by the Allegrini family, who are best known for Amarone in the Veneto region. Here you’ll find both hot-weather wines—a vermentino and a rosé—as well as luscious Super Tuscans. Dinner is at the hotel’s cozy restaurant. 
B, D • Podere Conte Gherardo

Today again focuses on Bolgheri, the area that put Super Tuscans on the map. Before World War II, this region produced only light-bodied, farmhouse reds meant for local consumption. After the war, Niccoló Antinori (father of Ludovico and Piero Antinori) began making a rosé at Gualdo al Tasso. Marketed with billboards along the Aurelia Way, the ancient Roman road that runs along the Tyrrhenian coast, this became Bolgheri’s first commercially successful wine.

But its fame was eventually overshadowed by Sassicaia, a powerful Bordeaux-style red that became the benchmark wine of Bolgheri. Today we’ll travel down a cypress-lined road known to every Italian school kid (from a poem by Giosuè Carducci) to Tenuta San Guido, where we’ll hear the history of Sassicaia, the first Super Tuscan, created by a piemontese transplant, the Marquis Mario Incisa della Rocchetta. 

Our last coastal winery is Le Macchiole, among the first to put down stakes in the Maremma. Uniquely, their focus is on pure varietals (cab franc and syrah) rather than blends. Transfer to Montalcino, where we will arrive late afternoon. Dinner in town at a lively, family-run restaurant.
B, D • Hotel Dei Capitani

History comes alive during our visit to Casato Prime Donne (aka Donatella Cinelli Colombini), on the cooler northern fringe of Montalcino. Donatella Cinelli Colombini is a powerhouse among female winery owners. She invented Italy’s Open Cantine Day, served as president of Donne del Vino (Women in Wine), and was the first Italian to hire an all-female winery staff. Her cellar is arrayed with paintings depicting historical turning points in Montalcino, so our hostess will provide an entertaining history as we tour the cellars. (And their wines are terrific!) 

Following lunch in town, we encounter some living history at Biondi Santi. Brunello’s beginnings in the 19th century go back to the agricultural experiments of Clementi Santi, a pharmacist and agronomist who is credited with isolating the Brunello clone. The family went on to transform rustic sangiovese into a long-lived powerhouse that gave Bordeaux a run for its money at the Paris and London Worlds Fairs in 1888 and 1891. Today it continues to set the benchmark for age-worthy Brunellos.

Our third winery visit is Poggio San Polo, another winery that makes exceptional classic-style Brunellos. Dinner is on your own in town. Buon appetito and pass the biscotti and vin santo!  
B • Hotel Dei Capitani

Art lovers will remember Sandro Chia as being part of the Neoexpressionist movement of the 1980s (along with Julian Schnabel, David Salle, Francesco Clementi, et al.). This Florentine native has also thrown himself into the art of wine, purchasing an ancient fortress near Montalcino, Castello Romitorio, and turning it into an exceptional winery. His Brunellos and Maremma-area wines are as impressive as the winery is unique, being populated with Chia’s sculptures, paintings, and eclectic antiques. 

After lunch, our afternoon tasting is at Casanova di Neri, whose single-vineyard Tenuta Nuova Brunello was Wine Spectator’s No. 1 of its Top 100 wines of 2007. Specializing in single vineyard Brunellos, they make several cru as well as an excellent base Brunello. You’ll see a new, state-of-the-art cellar tucked under a beautiful stone farmstead. 

Our farewell dinner back in Montalcino features Brunello-worthy Tuscan fare, such as gnocchi with wild herbs and beef braised in Brunello. 
B, D • Hotel Dei Capitani

A shuttle to Florence by noon and assistance with your travel plans. B

Want another Tuscan wine tour option? Check out our classic Tuscan Wine Treasures, a wine tour in Chianti, Montalcino, and Montepulciano. Or if you'd like some exercise along with your wine, see our Tuscan Trek wine & walking tour.

N.B.: We've had some issues with plagiarism this past year. So if you see something out there that looks really, really similar to Xtreme Tuscany and Tuscan Wine Treasures combined, remember this: We're the originals! Come to us.


Pisa or Florence (continental) or Rome (intercontinental). From Florence to Pisa by train, it takes only 1 hour, and trains leave twice an hour (see train schedule below). 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 about 3 hours to Pisa on the fast train (EuroStar); the latter requires reservations. 

Plan to land in Italy at least a day before the tour begins; that’s necessary to be at our starting point on time. We recommend spending the preceding night in Pisa. For hotel suggestions, consult a good hotel search engine or contact us for suggestions. 

Meeting point
Our meeting point is the Pisa train station, in front of the station. Please let us know if you are arriving by train that morning. 

Departure day
On our final day, we’ll have you back at the Florence train station by noon. (Drive time from Montalcino is approximately 2-1/2 hours.)

Trip extensions
ince our meeting place is Pisa, most people arrive a day early to spend the day sightseeing. One day is sufficient to cover the main sights. These include th Leaning Tower of Pisa, of course, but don’t ignore the Cathedral and Baptistry, the latter being noted for its remarkable acoustics (a guard demonstrates every half-hour) and its pulpit by Nicolo Pisano, an important precursor to the Renaissance. Pisa also has an excellent art museum filled with treasures by Simone Martini, Fra Angelico, Benozzo Gozzoli, and other medieval stars. Because Xtreme Tuscany does not include any time in Florence, we also recommend spending a few days there after our tour. The city 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. 


Italian train schedule
Click here for an 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.

Travel insurance
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 Go to “Pisa, Italy” and “Montalcino, Italy” to get a general idea of temperatures and forecast. In June, the weather should be spectacular, with daytime temperatures in the low 80s and nighttime temps cooling off to around 65º.

For cancellation policy & more, see our General Information page.

2018 dates
May 28–June 2

Single supplement: $350

Pisa train station

Florence train station

What's included
- 5 nights accommodations (double room) in two 3-star hotels, with breakfast buffet
- 4 gourmet dinners (three courses with wine)
- All wine tastings mentioned
- 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

Fabulous attention to detail in choosing hotels and restaurants, and an excellent, varied selection of wines and foods. Pat and Claudio were very knowledgable about the wines, landscape, and history. You two are perfect for this!
— Mary Beth Wyss, Dayton, OH