The Best Of Bolgheri: 10 Wineries You Can’t Miss

The birthplace of Super Tuscans, Bolgheri is home to Italy’s fabled Sassicaia red wine.
The entrance to a Bolgheri vineyard on a sunny day, with two large pine trees marking the entryway.

Located along the wild southern coastline of Tuscany, Bolgheri is the birthplace of Super Tuscans and home to Italy’s fabled Sassicaia red wine. Although its history is shorter than that of Chianti, it has become a coveted destination for enophiles and produces full-bodied reds with international grape varietals like Cabernet Sauvignon, Cabernet Franc, and Merlot (rather than Tuscany’s local Sangiovese grape). Intrigued? Read on to discover our favorite wineries in Bolgheri.

From Florence, the drive will take you about 1 hour and 40 minutes. You can also take the train to the “Castagnetto Carducci” train station which is about a 12-minute car ride from the town of Bolgheri itself. That being said, you’ll probably want access to a car if you’re visiting this area so you can check out a few wineries! I’d suggest visiting the town of Bolgheri and two wineries for a well-rounded day of wine tasting.

The Castle of Gherardesca in Bolgheri,  a medieval building with a crenelated roof and arched windows and doors.

The Town of Bolgheri

Boasting the longest cypress-lined road in Italy–with over 2,500 trees lining the 5-kilometer road–the drive into the town of Bolgheri will make you feel like you’re crossing over into the magical world of Italian wine. Once you park and walk through the gothic archway of the Castello di Gherardesca, you’ll find yourself in the heart of the hamlet. There are numerous wine bars in Bolgheri but my favorite is Enoteca Tognoni where you can get tasty food in a cozy atmosphere surrounded by walls of wine bottles. During busy months, you can even try a glass of the famous Sassicaia here for about €25.

The Best Super Tuscan Wineries In Bolgheri

These higher-end wineries offer tastings that range from €80-€120 per person.

Tenuta San Guido

First founded in 1944, Tenuta San Guido‘s Mario Incisa della Rocchetta is the name that spearheaded the Bolgheri region to international fame. This year, the estate celebrates the 50th anniversary of Sassicaia, a Bordeaux-style red wine made with Cabernet Sauvignon and Cabernet Franc. Tenuta San Guido also produces Guidalberto, a Cabernet Sauvignon and Merlot blend, and Le Difese, a Cabernet Sauvignon and Sangiovese blend.


Located just around the corner from the town of Bolgheri, Ornellaia is one of the area’s most renowned wineries. Along with Sassicaia, this was one of the first producers of Bolgheri Super Tuscans offering a Cabernet Sauvignon, Merlot, and Cabernet Franc blend. They also offer a 100% Merlot. Each year, Ornellaia invites an international artist to create a series of limited-edition wine labels as part of its Vendemmia d’Artista project.


Founded in 1977 by Maurizio Castelli, Grattamacco was one of the first Super Tuscan pioneers with a red that blends Cabernet Sauvignon, Merlot, and Sangiovese. The estate is set upon two hills that face the sea, granting a high altitude for the area, and features a single vineyard trained in the alberello style. Grattamacco was also the first estate to plant Vermentino in Bolgheri, a mineral-rich white wine.

Guado al Tasso at Tenuta Belvedere

Just off the parallel Via Aurelia, this wine is produced by the famed Tuscan winemaker Antinori. Ludovico Antinori founded the winery of Ornellaia and his brother, Piero Antinori, is another early Super Tuscan winemaker. Home to the beautiful “Bolgheri Amphitheater,” a plain encircled with rolling hills, the Guado al Tasso estate cultivates Cabernet Sauvignon, Merlot, Syrah, Cabernet Franc, Petit Verdot and Vermentino Nero and Bianco vines.

Tenuta Argentiera

Further south on the Via Aurelia, you’ll find Tenuta Argentiera. Named for the silver mines of the Etruscan era (argento means silver in Italian) this is the winery that is closest to the sea. You can taste wines down by the entrance or take the jeep tour around the vineyards and up the steep hill to a kind of wine fortress at the top with a clear view of the sea.

These more affordable wineries offer tastings that range from €20-€50 per person.

Castello di Bolgheri

With vineyards located on the historic Gherardesca lands surrounding the Castello di Bolgheri, you can enjoy a wine tasting while stepping back into history without ever leaving the town. The Gherardesca family ruled most of the region since the middle ages and without their land holdings, Super Tuscan wine may have never existed. Remember Mario Incisa della Rocchetta? He married Clarice Gherardesca, which is why he was given the plot of land that would eventually become the birthplace of Sassicaia.

Caccia al Piano

Right next door to Ornellaia on Strada Provinciale Bolgherese, Tenuta Caccia al Piano was first established in 1868 but their wine-making production began in 2003. While they may be a newer estate, their wines are affordable and noteworthy. Their olive oil farm, begun in 1987, is right across the street from the winery where you can enjoy a delicious Tuscan lunch outside in their olive grove.

Podere Sapaio

The cellars of Podere Sapaio are closer to the Castagneto Carducci train station in Donoratico and offer €10 tastings but you can also do more picturesque tours of the vineyard on request for €50. The characteristic crown on their label is a tribute to the nobility of wine, and while they are also new to the wine region (production started in 2000), their two Bolgheri DOC wines are garnering warranted attention.


30 minutes north of Bolgheri in Riparbella, Duemani is a biodynamic winery founded in 2000 by Elena Celli and Luca D’Attoma. In addition to fruity reds aged in barrels, the estate produces a 100% Syrah Rosé and 100% Grenache wine aged in amphora.


Another winery located in Riparbella, Caiarossa wine-making follows the principles of Feng Shui. With carefully constructed cellars, they follow choices of color, placement, and materials. Who can say if the wines appreciate it, but guests certainly do!

Many bunches of different grapes in crates with the vineyard in the background.

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