Which restaurant on this list holds a Wine Spectator award?

Taverna del Grappolo Blu in Montalcino is the only restaurant on this list with a Wine Spectator award. The award is a Wine Spectator Award of Excellence for 2025. Its wine list runs to around 1,085 selections weighted toward Brunello.

Which restaurants on this list serve a tasting menu?

Tasting menus on this list are at Campo del Drago in Castiglion del Bosco and Boccon DiVino in Montalcino. Campo del Drago serves a tasting menu and a la carte of contemporary cooking from the estate organic kitchen garden, with a sommelier-led list. Boccon DiVino serves a tasting menu and a la carte of truffle-centric Tuscan food in a farmhouse.

Which neighborhoods are these wine restaurants in?

The restaurants on this list are in Montalcino, Castiglion del Bosco and Castelnuovo dell'Abate. Montalcino has Taverna del Grappolo Blu, Boccon DiVino and Osteria di Porta al Cassero. Castiglion del Bosco has Campo del Drago, the modern Tuscan fine-dining restaurant. Castelnuovo dell'Abate has Vineria Aperta, the Tuscan wine bar.

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Best Restaurants for Wine Lovers in Montalcino

Five restaurants in our Montalcino guide have exceptional wine programs. Taverna del Grappolo Blu, Boccon DiVino and Osteria di Porta al Cassero are in Montalcino. Campo del Drago is in Castiglion del Bosco, and Vineria Aperta is in Castelnuovo dell'Abate.

Taverna del Grappolo Blu holds this list's only Wine Spectator award, an Award of Excellence for 2025, with around 1,085 selections weighted toward Brunello.

Campo del Drago holds two Michelin stars for 2026, with over 700 labels weighted toward Brunello di Montalcino.

Vineria Aperta has over 3,000 wine labels focusing on Brunello di Montalcino, including natural wine, and Star Wine List recognition for 2026. Boccon DiVino serves a tasting menu and a la carte.

Osteria di Porta al Cassero is a family-owned osteria serving Tuscan peasant cuisine paired with Brunello wines.

How this list is chosen: Restaurants with a Wine Spectator Restaurant Award or a deep wine list, listed alphabetically. Updated October 8, 2026.

Boccon DiVino
Deep wine list
A Michelin Plate-recognised farmhouse restaurant on the outskirts of Montalcino, Boccon DiVino occupies the mid-tier of the town's dining scene with authentic Tuscan cooking at accessible prices. The rustic interior gives way to a summer terrace with open countryside views, making it a reliable address for regional dishes rooted in local ingredients.
Campo del Drago
2 Michelin stars · Deep wine list
A two-Michelin-star restaurant within the Rosewood Castiglion del Bosco estate in Montalcino, Campo del Drago reaches the table via a dirt track through Val d'Orcia and a medieval hilltop village. Chef Matteo Temperini builds his contemporary menus around produce from the estate's own kitchen garden, backed by a wine list of over 700 labels weighted toward Brunello di Montalcino.
Osteria di Porta al Cassero
Deep wine list
Among Montalcino's osterie, Porta al Cassero occupies the mid-range bracket where Tuscan regional cooking meets the town's defining wine identity.4 across nearly 1,200 Google reviews, it offers a reliable point of entry into the pairing tradition that has made this hilltop comune one of Italy's most food-serious destinations.
Taverna del Grappolo Blu
Wine Spectator Award of Excellence · Deep wine list
Reached by a steep flight of stone steps off one of Montalcino's narrow lanes, Taverna del Grappolo Blu has held Michelin Bib Gourmand recognition in both 2024 and 2025 for its direct Tuscan cooking and a wine list of around 1,085 selections weighted toward Brunello. Pici with ragù and tripe anchor the menu; the atmosphere is informal, the service attentive, and the pricing stays at the accessible end of the town's dining spectrum.
Vineria Aperta
Deep wine list
The setting places it outside the main tourist circuit, which shapes both the crowd and the pace. For visitors already covering the Brunello zone, it offers a grounded alternative to the hilltop town's busier enoteca options.

Planning restaurants for wine lovers in Montalcino

Which restaurant on this list holds a Wine Spectator award?: Taverna del Grappolo Blu in Montalcino is the only restaurant on this list with a Wine Spectator award. The award is a Wine Spectator Award of Excellence for 2025. Its wine list runs to around 1,085 selections weighted toward Brunello.
Which restaurants on this list serve a tasting menu?: Tasting menus on this list are at Campo del Drago in Castiglion del Bosco and Boccon DiVino in Montalcino. Campo del Drago serves a tasting menu and a la carte of contemporary cooking from the estate organic kitchen garden, with a sommelier-led list. Boccon DiVino serves a tasting menu and a la carte of truffle-centric Tuscan food in a farmhouse.
Which neighborhoods are these wine restaurants in?: The restaurants on this list are in Montalcino, Castiglion del Bosco and Castelnuovo dell'Abate. Montalcino has Taverna del Grappolo Blu, Boccon DiVino and Osteria di Porta al Cassero. Castiglion del Bosco has Campo del Drago, the modern Tuscan fine-dining restaurant. Castelnuovo dell'Abate has Vineria Aperta, the Tuscan wine bar.