How to Have a ‘Sideways’ Visit in Tuscany

We may earn a commission from links on this page. Learn more

Sideways, the 2004 film about wine and so much more, celebrates its 20th anniversary in 2024. Starring Paul Giamatti (Miles), Thomas Haden Church (Jack), Virginia Madsen (Maya), and Sandra Oh (Stephanie), Sideways is a favorite film of wine lovers as it features a drive through California wine country and several discussions—some hilarious—on wine, wine-tasting, vineyards, and vintages.

Rewatching recently, one discussion caught my ear. It’s when Miles ends up at Maya’s house and they discuss what particular vintage got them into wine. For Miles, it was a French Cheval Blanc (ironically, a wine made from Merlot grapes). But for Maya, it was an Italian wine.

An ’88 Sassicaia:

                     How long have you been into wine?

                     I started to get serious about seven 
                     years ago.

                     What was the bottle that did it?

                     Eighty-eight Sassicaia.

In a movie filled with delectable California wines, I was of course drawn to the mention of an Italian one.

What is Sassicaia?

According to the San Francisco Wine School, Sassicaia is

a wine known and loved the world over. From a beautiful coastal hamlet in Tuscany, this Super Tuscan blend is hands down Italy’s most famous wine. It is also the world’s second most counterfeited wine after Chateau Petrus.

Italy’s first Super Tuscan, Sassicaia is a blend of 85% Cabernet Sauvignon, 15% Cabernet Franc. “Marchese Mario Incisa della Rocchetta began a revolution in Tuscan winemaking,” continues SFWS, “and not in the traditional wine region of Tuscany, Chianti Classico, but at a large farm in the village of Bolgheri located close to Tuscany’s Mediterranean coastline in the southwestern part of the province.”

Where Is Sassicaia Produced?

The “most famous Tuscan wine” comes from one family-owned vineyard located in the province of Livorno, not far from Pisa. “Mario Incisa’s love of good wine made him plant Cabernet vines in 1942 [at Tenuta San Guido] for what was to become Sassicaia,” explains the Tenuta San Guido website. “So exceptional [are the Sassicaia wines] that they deserve a DOC of their own (DOC Bolgheri Sassicaia) which is the only DOC in Italy to be included entirely in a property.

“From 1948 to 1967, Sassicaia remained a strictly private domain and was drunk only on the estate. The 1968 vintage was the first to be put on the market, with a welcome worthy of a Bordeaux Premier Cru.”

In addition to the Sassicaia vintage, Tenuta San Guido produces the much more affordable Le Difese and Guidalberto Tuscan red wines, respectively a Cabernet and a Cabernet-Merlot blend.

Can You Stay at Tenuta San Guido and/or Tour Vineyards?

Alas, no. You can not stay at Tenuta San Guido, nor can you tour its vineyards. The family makes it clear on their website that they are tired of getting asked this question, answering thus:

Ladies and Gentlemen,

We inform you that Tenuta San Guido does not organize guided tours of the cellar or the vineyards.

Furthermore, Tenuta San Guido does not market its products directly but through historical and consolidated partners.

But, You Can Wine and Dine at Enoteca San Guido

I suppose the family maintains their privacy and wine-growing secrets by keeping their vineyards closed to visitors. But they do provide a venue where you can dine on local fare while sipping a Sassicaia.

Osteria Enoteca San Guido is in Località San Guido in the medieval Tuscan village of Castagneto Carducci. That’s about one hour south of Pisa, two hours southwest of Florence, and three hours north of Rome (should you be going by car). A favorite place to stay in these parts is the coastal town of Castiglioncello, which is about half an hour north of Castagneto Carducci.

Tour the Wildlife Refuge Near the Vineyards

You can also visit—with a reservation, on Saturdays and Sundays—the wildlife refuge near the Sassicaia winery.

The Marchese was at the forefront of conservation, transforming his old hunting lodge into a bird refuge. The Padule di Bolgheri “extends for about 513 hectares and is entirely included in the territory of the Municipality of Castagneto Carducci,” explains another page of the Tenuta’s website.

“In 1977 the Padule di Bolgheri Wildlife Refuge was among the first Italian wetlands to be awarded the recognition of ‘Zona Ramsar’ (Wetland of International Importance) precisely for its peculiarity of guaranteeing numerous species of water birds the presence of suitable environments to the winter break and to the spring transit.”

The Padule di Bolgheri is open with reservations required ( ), on Saturdays and Sundays, with two visits, at 09:30 and 14:00.

They are kind enough to include a map of the property:

DOC Bolgheri Sassicaia map

Follow the Wine and Olive Oil Trail

Tuscany’s tourism board also recommends the Etruscan Coast Wine and Olive Oil Trail. In addition to Bolgheri DOC, this wine trail passes through several DOC territories including Terratico di Bibbona, Montescudaio DOC, and Val di Cornia DOC.

What better way to have a Sideways adventure through Tuscany than to follow a wine route?

Go On A Private Super Tuscan Tour

These folks who offer a private Bolgheri and the Super Tuscans tour. They organize lunches at Osteria Enoteca San Guido and take guests around to sample Ornellaia and Le Macchiole Super Tuscan wines. There are also several private and small group tours of the Bolgheri area that include Super Tuscan tastings and walkabouts in the villages where these vintages were created.

How Else Can You Try Sassicaia?

You can actually buy Sassicaia online these days. I guess Italian Amazon and online wine sellers like, Total Wine, and Vivino are the “consolidated partners” that Tenuta San Guido mentioned on their website.

Anyhow, if you’re willing to invest in a Sassicaia or simply want to drink it with a cheeseburger (or whatever it is that Maya eats with her wines), it is apparently the most popular Italian wine to buy online.

Watch Sideways (Again)

Sideways is currently streaming on Hulu, Amazon Prime Video, and HBO Max.

Last updated on July 25th, 2023

Post first published on September 9, 2022

Similar Posts