DAY 1 – TOUR ORNELLAIA & THE MAREMMA’s PIONEERS

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

After lunch we go one one of Bolgheri’s brightest stars: Ornellaia, founded by Ludovico Antinori. A visit to their vineyards will show why the geography of Bolgheri is so well suited to cabernet sauvignon, cabernet franc, merlot, and syrah—French grapes that triggered the Super Tuscan phenomenon. In the cellar, we’ll hear about the meticulous care that helps explain why Ornellaia has become such a prized cult wine.

If there’s time and interest, we’ll do an impromptu stop at Michele Satta, one of Bolgheri’s pioneers in the 1980s. At thismid-sized, family-owned winery, you’ll find both blended and pure sangiovese (including a fantastic rosé), plus an excellent vermentino, the heat-loving white grape of coastal Tuscany. Then, after settling into our seaside 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 • Hotel Alta Vista

DAY 2 – BOLGHERI’s NEW KIDS ON THE BLOCK 

We begin the day on the Via Bolgherese,the wine road in Bolgheri that’s lined with boldface names. Here we’ll visit a relative newcomer: Poggio al Tesoro, founded by the Allegrini family, who are best known for their Amarone wine in the Veneto region. Here in Tuscany they make both hot-weather wines—a vermentino and a rosé—as well as luscious Super Tuscans. 

Lunch is in the village of Bolgheri, where restaurants pour Sassicaia and other cult wines by the glass. Our next coastal winery is Le Macchiole, among the first to put down stakes in the Maremma. Uniquely, their focus is on pure varietal wines (most notably cab franc and syrah) rather than blends typical of Bolgheri. Capping off the afternoon is a visit to Campo alla Sughera, another young enterprise (f.1998) built from scratch by a German family, the Knaufs, who preside over a building-materials multinational. Their love of technology blends with tradition in this gravity-fed winery. Dinner is at the hotel’s fine restaurant. B, D • Hotel Alta Vista

DAY 3 – BEYOND BOLGHERI

Our last coastal winery is Petra. It’s also the newest on this portion of the tour, located just outside the Bolgheri DOC zone. Petra is 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, which we’ll try over lunch at the winery. Then we transferto Montalcino (90 min.), the highest wine zone in Tuscany. As we ascend its southern slope, we’ll stop en route at the storied Col d’Orcia for our first sip of Brunello di Montalcino. Despite being the third largest winery in the DOCG zone, it owners run it like a small family farm, with scrupulous attention to detail. Dinner is in town. B, D • Hotel Dei Capitani

DAY 4 – MASTERING MONTALCINO WINE

The big, earthy Brunellos of Uccelliera have a cult following. Named after the many birds (uccelli) in the area, Uccelliera was started in 1986 when a native son had the chance to buy an old farmhouse on the Ciacci Piccolomini property. After visiting this small boutique winery, we’ll go to the mother ship: Ciacci Piccolomini di Aragona, a southside estate with great wines—and a great Cinderella story to match, involving aristocrats, a vineyard manager, and the Church. After lunch in town, history comes alive at 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. Dinner is on your own in town. B • Dei Capitani

DAY 5 – XTREME BRUNELLO

By universal acclaim, Illy is Italy’s best espresso. In 1997, Francesco Illy—company VP, grandson of the founder, and the artistic one in the Trieste-based family—bought land from a shepherd in Montalcino. He went on to plant the densest vineyard in all of Italy at his Le Ripi winery. We’ll find out why, taste his biodynamic wines (including that from the “bonsai” cru), and see his cellar, whose design (by his architect son) is based on the ancient “golden ratio.” 

After lunch, our afternoon tasting is at Casanova di Neri. Specializing in single vineyard Brunellos, they make several cru as well as an excellent base Brunello. (Theirsingle-vineyard Tenuta Nuova Brunello was Wine Spectator’s No. 1 in the Top 100 wines of 2007.)You’ll see a state-of-the-art cellar tucked under a beautiful stone farmstead.  Our farewell dinner in Montalcino features Brunello-worthy Tuscan fare. B, D • Hotel Dei Capitani

DAY 6 – ARRIVEDERCI! 

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