6 Siena Vineyard Tours to Build a Day Around

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, handmade pici or tagliatelle, and a Tuscan dessert with a chef such as Alexandra or Jacomo. Tour the winery and cellar, then eat your meal with Rosso and Brunello pairings. Transport from Siena or Florence costs extra.

“This was an unbelievable experience - the views over the vineyard, the quality of the food, the amazing instruction, and the wonderful teacher. It could not have been a more enjoyable and worth it experience. Thank you!!”

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2.Vespa Tour with Lunch&Chianti Winery from Siena

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

Ride a Vespa through Chianti’s vineyard roads, stopping in Castellina, Radda, and Monteriggioni before a winery visit with wine tasting and a light lunch. You may drive your own scooter, but you must pass a safety test, hold an international driving permit, and have real Vespa experience.

“They didn’t show up even though I had a confirmation with our hotel as pick up point and didn’t refund our 600.00!”

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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. Walk the vines, visit the cellar, taste five wines, and share a seasonal Tuscan meal. Guides including Maia, Mya, and Gianluigi bring clear explanations and plenty of personality.

“It was amazing, the guide, location, food everything was awesome! I would 100% recommend it!”

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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

Spend about eight hours in Brunello country with an English-speaking driver-guide, visiting two boutique wineries, tasting cellar wines, enjoying a pairing lunch, and exploring Montalcino. Pickup, return transport, bottled water, Wi-Fi, and an air-conditioned vehicle are included.

“Patrizio was great. Very informative. Each of the wineries was unique and beautiful. And of course the wine was also excellent.”

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5.From Siena/Chianti: Dinner & Drinks in the Chianti Vineyards

★★★★★★★★★★4.0 · 95 reviews · from $123

Meet at Siena train station at 6:00 PM for a five-hour evening in Chianti. A driver-guide takes you to a Tuscan farm for wine tasting, a winery walk, chapel visit, sunset aperitivo, and a four-course dinner with roast meats, vegetables, dessert, wine, and water. Guides may speak English, Italian, or Spanish.

“amazing, would really recommend this if you want good food, amazing wine and excellent staff who will teach you alot about the wine and how to taste it. thank you so much for the wonderful evening”

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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 through the Chianti Hills, with stops in Castellina in Chianti and an exclusive winery. Guides such as Lorenzo, Francesco, Gabriele, and Sam lead the small-group outing, which includes wine tasting and dry snacks. Bring a license and credit card if driving.

“Fantastic is an understatement. Gabriele was a great guide. Very knowledgeable and passionate about Tuscany and the region. Highly recommend.”

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