Tough Tuscany wine Tours

Tough Tuscany wine Tours


Spotlight on Brunello & Bolgheri’s Super Tuscans


Tour Overview:


Enjoy private, sit-down tastings at Tenuta San Guido (Sassicaia), 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

If you’re really, really passionate about wine and want an educational focus to your vacation, this tour is for you. XTREME TUSCANY was designed as a parallel to XTREME PIEDMONT, which came about when the Society of Wine Educators asked us to organize a tour in Piedmont. “Something that really focused on the wine,” they said, skipping incidentals like cooking lessons, truffle hunts, and food fairs. Something for people who wanted to learn as much as possible about the region’s most important wines. We liked XTREME PIEDMONT so much that we’ve kept it on our calendar ever since and started XTREME TUSCANY the very next year. Both XTREME tours include an extra tasting or more per day, and both include some hard-to-get-into estates that we visit only on these tours.


XTREME TUSCANY starts in an area of Tuscany that most Americans never see: the Etruscan coast, also called the Maremma. For centuries, this was swamp land, and malaria kept settlers away or high up in the Apennine mountains, which skirt the coast. It wasn’t until Mussolini drained the swamps that it opened up to farmland. Gradually, the fields of strawberries and horse farms were supplanted by vineyards. And very good vineyards at that, which gave rise to the Super Tuscan juggernaut.


The story begins with the Marquis Mario Incisa della Rocchetta, whose wife inherited Tenuta San Guido and a tract of land called Sassicaia, named after the rocks, or sassi, pulled from the soil. He wanted to make an Italian cabernet, using French grapes under a Tuscan sun. The gravely soil on the Marquis’s properties reminded him of Grave, Bordeaux, another alluvial region close to the sea. In creating Sassicaia—an Italian wine using French varietals, nurtured in barrique, and intended for long aging—he created a revolution, not only in sleepy Bolgheri, but across the peninsula.


Although Super Tuscans are now widespread, Bolgheri is where these wines truly excel. We’ll visit pioneers like Sassicaia, Ornellaia, Grattamacco, and Michele Satta, as well as newcomers like Petra, whose stunning architecture alone is worth a visit (by Swiss architecture Mario Botta).


The tour’s second part moves inland to a much older region: Montalcino, noted since the time of Charlemagne for its excellent reds. Here, too, we’ll visit pioneers and iconoclasts. We’ll do a barrel tasting at a boutique producer who will discuss the evolution of Brunello in botte. We’ll stop at Banfi, an American-owned estate whose clonal research in the 1980s and ’90s helped Brunello leap to the next level. We’ll visit Biondi Santi, where Brunello began in the 1880s; Casanova di Neri, whose Brunello cru have attained cult status; and Castello di Romitorio, populated with wonderful artwork by owner Sandro Chia, a leading figure in the international Neoexpressionist movement of the 1980s.





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 brand-new, state-of-the-art cellar, completed at the beginning of 2008. 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



Pisa or Florence (continental) or Rome (intercontinental). To land in Pisa or Florence, you’ll need to connect somewhere in Europe. From Florence to Pisa by train, it takes only 1 hour, and trains leave twice an hour (see 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, such as TripAdvisor or Venere.


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.)


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.


Trip extensions

Since 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. And it’s just a hop and a skip to Rome on the EuroStar express train (1 hr 35 min).


Travel insurance

This is recommended to protect you from needless loss caused by last-minute cancellations, lost luggage, and more. One source is Travelex Insurance:, (800) 228-9792 (please use our compay code: 21-0043 LDV).



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.

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