Winery Tours in Siena: the 6 We Rate

1.A Brunello Cooking Class with Vineyards View Winery

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

Spend four hours at Castello Tricerchi near Montalcino making filled pasta, pici, and a Tuscan dessert with a chef such as Alexandra, Gaia, or Jacomo. Tour the castle and cellar, then eat your meal with Rosso and Brunello on a terrace above the vineyards. Siena and Florence pickup can be arranged for an added fee.

“Our cooking instructor was wonderful, and very patient! The view for cooking and the meal was amazing.”

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2.Vespa Tour with Lunch&Chianti Winery from Siena

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

Ride a Vespa convoy through Chianti’s vineyards, olive groves, and hill towns on a 6.5-hour outing from Siena. You can drive your own scooter or ride with an escort, then visit Casale dello Sparviero for wine tasting and a light lunch. An international driving permit and real scooter experience are required.

“We had a very fun and knowledgeable tour guide who made the trip such a great time! It was such a beautiful ride and the wine was amazing! We would definitely do it again!”

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3.Organic Winery Tour and Wine Tasting

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

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 and winemaking before five wine tastings paired with seasonal Tuscan food. Plan on taking a taxi from central Siena.

“We absolutely loved our experience. Gianluigi was very well informed, explicative and such a pleasant speaker, we could listen to him talking about wine for hours. The winery is beautiful, we tasted several wines together with delicious food. We are very glad we chose this activity during our stay in Siena.”

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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 small group of up to eight, with an English-speaking driver-guide, to two boutique Brunello wineries. Tour historic cellars, taste local wines, pause in Montalcino, and enjoy a three-course wine-pairing lunch. Guides such as Niccolò, Stefano, and Patrizio are praised for their local wine knowledge.

“The only issue was the original description I signed up for makes you think we would go to winery in Montalcino then lunch somwhere with tastings then also to Montepulciano for another tasting. I really wanted to go to BOTH and actually we only went to 2 places (not 3) and never went to Montepulciano so I thought the price I paid $577.92 fo 2 people was way overpriced for this experience.”

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5.winery tour, wine tasting and lunch

★★★★★★★★★★5.0 · 70 reviews · 2.5 hours · from $77Best value

Walk through Chianti vineyards to the 1100s church of San Giorgio a Lapi, see frescoes by Nasini, tour the cellar, then enjoy a wine-paired Tuscan lunch on a panoramic terrace. Guides may include Jesse, Gabriele, or Giuseppe. The small group is limited to 10 people.

“Beautiful setting and excellent tour. Food and wine pairings were really good and no hard sell at the end.”

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6.Day Tour in a Vintage Fiat 500 with Winery

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

Drive a manual vintage Fiat 500 from Siena or Badesse through the Chianti hills, stopping in Castellina in Chianti and at a private winery for wine and local snacks. Guides such as Lorenzo, Francesco, Gabriele, and Sam lead small groups of up to eight. Bring a license, credit card, and confidence with stick-shift driving.

“My wife and I had one of the best days of our lives driving a 1968 Fiat 500. Lorenzo is an amazing guide and a wonderful person. He took us through spectacular countryside and was very concerned for everyone’s safety. Advise to customers: Do NOT overestimate your driving ability, especially on a Vespa. Either ride with someone who has experience, or partner up with someone who can drive a stick and take a Fiat. (The Vespas and Fiats travel together in one large group.) The lunch/wine tasting was a fantastic experience. Ivan was a superb host who gave an enjoyable and informative tour of the winery. We stopped for gelato…”

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