Top 9 Wine Tours in Siena

1.San Gimignano, Siena, and Chianti Wine Tour

★★★★★★★★★★4.5 · 3,762 reviews · from $164Our pick

Travel from Florence to Siena, a Chianti winery, and San Gimignano in about nine hours. Expect an air-conditioned minibus or coach, multilingual guidance, five wine tastings, Tuscan specialties, and free time in both medieval towns. Guides such as Marco, Lyla, Marta, and Enrieta are praised for keeping the day clear, friendly, and on schedule.

“The experience couldn’t get any better. Marco is an excellent guide and a person! Highly recommended. I went by myself, but made very good friends along the way 💫 Italy is mesmerizing and do not hesitate to take this tour 🥰🌟 p.s. I would recommend to get lunch at the winery. Grazie”

Check availability →Read our full review

2.Montepulciano: Wine Tasting and Cellar Tour

★★★★★★★★★★4.8 · 545 reviews · 1 hour · from $38Best value

In Montepulciano’s car-free center, a guide such as Mirko, Debi, Emilio, or Ron leads you through historic underground cellars, explains Nobile di Montepulciano and local tufa soil, then serves five DOC and DOCG wines with pecorino, crostini, and bruschetta.

“We loved our tour, we have been on many wine tours and this was up there with the best.”

Check availability →Read our full review

3.Total Immersion Wine Tour in Chianti

★★★★★★★★★★4.9 · 430 reviews · 2 hours · from $47

At Fattoria di Montemaggio, high in the Chianti hills, Francesco, Ilaria, or another member of the family team leads you through the vineyard, cellar, and wine-tasting room. You’ll learn about organic farming, Chianti Classico’s Black Rooster, wine tasting, grappa, and five estate products served with local snacks.

“the guide was very freindly and he really created an experience we will not forget.”

Check availability →Read our full review

4.Brunello di Montalcino Guided Wine Tour W/ Lunch

★★★★★★★★★★4.9 · 357 reviews · from $203

Travel from Siena in a small minivan with an English-speaking guide to three Brunello wineries, Montalcino, and Sant’Antimo Abbey. Expect cellar visits, tastings, a family-run winery lunch, and plenty of Tuscan scenery. Guides have included Marco, Georgia, Paolo, Daniele, and Giulia.

“All around a terrific day. Thought the tour might be too long, but time flew, wine was amazing, lunch delicious and Mattieo, a former vintner, was extremely knowledgeable and passionate about Tuscany and the wine and olive oil that it produces. Highly recommend!”

Check availability →Read our full review

5.Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

★★★★★★★★★★4.6 · 324 reviews · 1.5 hours · from $69

Meet your English- or Italian-speaking sommelier at Castello Tricerchi for a vineyard walk, castle and cellar tour, three local wine tastings, Tuscan snacks, and a three-course lunch. Guides such as Alice, Alessio, and Alessandro explain the estate, Brunello production, and food pairings. Arrive 15 minutes early, since latecomers are not accepted.

“Very educational, the wine history and description of the areas and the Brunello and Rossi di Montalcino were very good. Our meal was quite substantial with cold meats and cheeses as well as a small bowl of pasta followed by coffee and small cake. Very historic building with beautiful views. I think it was well done and the young gentleman spoke very good English and was extremely knowledgeable. Steve from Australia”

Check availability →Read our full review

6.Tuscany Hills Wine Tour

★★★★★★★★★★4.1 · 323 reviews · from $146

Set out from Siena for a full day through Chianti and Val d’Orcia. Taste wines with local snacks at two wineries, then enjoy free time in Pienza and Montepulciano. Guides such as Marta, Vincenzo, Lucia, and Alberto have earned praise for their warm, informative commentary. Lunch is not included, and moderate walking is required.

“One of the best Italian trips I’ve ever been to. To be honest I’m not a fan of wine but the wine provided is good and the cheeses/olive oil/salami are some of the best. Talking about the main travel, you’ll have time to take enough panaromic pictures of this fantastic place. Oh and I must say the lady guide of my group is one of the bests I’ve ever seen.”

Check availability →Read our full review

7.Educational Wine Tour & Tasting

★★★★★★★★★★5.0 · 203 reviews · 3 hours · from $100Top rated

Spend three hours at Azienda Agricola La Lastra, 2 kilometers from Siena, learning how organic grapes move from soil to bottle. Guides including Christian, Renato, Maya, and Gianluigi explain vineyard work and cellar production in clear terms. Taste four local organic wines with seasonal Tuscan food, including vegetarian and gluten-free options when requested.

“This was the best winery tour we had. Maya was great explaining everything to us and the wine and lunch were amazing”

Check availability →Read our full review

8.Montalcino: Guided Winery Tour and Wine Tasting

★★★★★★★★★★4.8 · 200 reviews · 1h 45m · from $53

Spend 105 minutes at Corte Pavone Winery near Montalcino with an English or Italian guide. Walk through the vineyards, visit the cross-vaulted cellar, learn about biodynamic wine-making, and taste six wines. Choose from Brunello, Corte Pavone, Maremma and Montalcino, or Valdifalco tasting themes.

“Amazing experience! The area is absolutely beautiful, and the tour offers incredible insight into Brunello wine. Everyone was so friendly, and the wines were truly exceptional. 100/100 — I’d recommend this to anyone!”

Check availability →Read our full review

9.Montepulciano: Winery Tour and Tasting

★★★★★★★★★★4.6 · 187 reviews · 1.5 hours · from $41

Meet at Talosa Cantina Storica for a 1.5-hour visit below Montepulciano’s streets. You’ll walk through old vaults and tunnels, hear about the cellar’s past, and taste four Tuscan wines with a sommelier such as Luigi, Flavio, or Hector. Bread, water, and traditional appetizers are included.

“Better than expected! The tour isn´t that big but it was really okay!”

Check availability →Read our full review