5 Winery Tours in Siena to Build an Afternoon Around

1.A Brunello Cooking Class with Vineyards View Winery

★★★★★★★★★★5.0 · 221 reviews · 4 hours (approx.) · from $313Our pick

Spend about four hours at Castello Tricerchi near Montalcino, making filled pasta, pici, and a Tuscan dessert with a chef such as Alexandra or Jacomo. Tour the winery and cellar, then eat your meal with Brunello and Rosso di Montalcino on a terrace above the vines.

“Amazing Experience! There was so much food and wine that we left uncomfortably full but happy. The recipes were simple to make and delicious. The chef was very friendly, knowledgeable, welcoming and fun to cook with.”

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2.Vespa Tour with Lunch&Chianti Winery from Siena

★★★★★★★★★★4.0 · 126 reviews · from $168

Ride a Vespa in convoy from Siena through Chianti, with stops in Castellina, Radda, and Monteriggioni. You can drive if you have real scooter experience and an international license, or ride as a passenger. The day includes a winery visit, wine tasting, and a light Tuscan lunch.

“It was great fun for our kids and us! Super way to see the country side. Lunch was very light just a meat and cheese board. Very young guides.”

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3.Organic Winery Tour and Wine Tasting

★★★★★★★★★★5.0 · 111 reviews · 2.5 hours · from $88Best value

Spend 2.5 hours at Azienda Agricola La Lastra, an organic winery about 2 kilometers from Siena. Guides such as Maia, Mya, and Gianluigi explain vineyard care, cellar work, and wine tasting before pairing five wines with seasonal Tuscan food and garden vegetables.

“The tour provided by Maia was incredible. She is both knowledgeable and professional, while being simultaneously engaging. Her passion for organic viniculture was contagious, and we cannot wait to taste more of this fine Tuscan wine. Thank you so very much.”

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4.Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch

★★★★★★★★★★5.0 · 103 reviews · 8 hours (approx.) · from $276

Travel from Siena in a luxury air-conditioned vehicle to two boutique Brunello wineries, with cellar visits, tastings, a three-course pairing lunch, and time in Montalcino. Guides such as Niccolò, Stefano, and Luigi add local wine knowledge, though the exact stops can vary.

“Thank you very much Nicolo for the best wine tour ever. We enjoyed both vignards, the food was excellent.”

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5.Day Tour in a Vintage Fiat 500 with Winery

★★★★★★★★★★4.4 · 41 reviews · from $146

Drive an original manual Fiat 500 from Siena through the Chianti hills, stopping at Castellina and a countryside winery for wine and dry snacks. Guides such as Lorenzo, Francesco, Gabriele, and Sam add local stories. Drivers need a license and credit card for the rental deposit.

“It was really wonderful, sam was the perfect guide for showing us around the beautiful toskana”

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