Beginning as early as the 1960s, a small group of vineyards broke with the Italian laws governing Chianti production, particularly the blending of non-traditional grapes. The result was a superior class of wines from the Bolgheri and Chianti Classico regions we now call Super Tuscans, including (arguably) the four most prestigious wines in Italy. Any oenophile’s vacation in Tuscany would be incomplete without an outing to one if not all of these sites.

Sassicaia, first sold commercially in 1968, fathered the Super Tuscan category of wines. Very much in the French tradition, Sassicaias slanted heavily toward Cabernet Sauvignon, with Cabernet Franc as the secondary grape. To taste them on site, head to the producer Tenuta San Guido’s prime Italian real estate in Bolgheri. All visits and tastings are hosted by Consorzio La Strada del Vino Costa degli Etruschi. Contact them at 0565 749705 or turismo@lastradadelvino.com to make an appointment. As an aside, Castello di Casole shares a connection to Sassicaia and its creator and proprietor, Mario Incisa Della Rochetta, through his grandson Piero Incisa della Rocchetta. A third-generation winemaker, Piero oversaw the production of Castello di Casole’s prized vintage, Dodici, meaning “Twelve” in Italian. Piero’s participation at Castello began when he created a test production of wine to determine if the terroir – the various components on an estate such as soil, climate, and conditions that contribute to its unique character – could produce wines of consequence. His first experiment yielded 12 barrels, or barriques, as they are called in French. As anticipated, these 12 barriques yielded a surprisingly elegant yet complex wine, combining the quintessential Tuscan characteristics.

Tenuta dell’Ornellaia, the producer of Ornellaia can also be found in Bolgheri and although the vineyard is much newer, opening in 1981, its reputation is equally excellent. The flagship wine is roughly half Cabernet Sauvignon with Merlot, Cabernet Franc and just a touch of Petit Verdot rounding out the blend. To arrange a tasting, tour the estate and even have dinner on site, request a reservation on the vineyard’s website. Be sure to taste Ornellaia’s spectacular Merlot Masseto while you’re there.

To check out Solaia, dating back to 1978, and Tignanello, dating back to 1971, head from Bolgheri to the Chianti Classico region between the little villages of Monteridolfi and Santa Maria, where the two are close together. Both are produced by Antinori at Tenuta Tignanello, although the wines are quite opposite.

Tignanello is roughly 80% local Sangiovese grapes rounded out with Cabernet Sauvignon, while Solaia is 75% Cabernet Sauvignon finished off with Sangiovese (both are rounded off with a touch of Cabernet Franc). Visits are normally reserved for experts and professionals but private tours are not unheard of. Chat with the concierge at Castello di Casole about wrangling a tour guide with the right connections.

Of course, you don’t have to go far to taste Italy’s best Super Tuscans. Castello di Casole’s Ristorante Tosca is home to hundreds of vintages from leading wineries in Tuscany, and in this case the guide, (i.e. Castello di Casole’s immensely knowledgeable sommeliers), come right to you.