Top Siena Wine Tasting Tours - page 3

San Gimignano, Chianti and Montalcino Tour through Tuscan wine

11 hoursFree Cancellation

Surround yourself with the unrivaled scenery of Valle de Orcia while trying some of its epicurean delights on a private tour from Siena. Begin in the hill town of Montalcino, where you'll sip on locally produced wine at a popular winery. Later, head to the historic center of UNESCO-listed Pienza, where you'll enjoy free time to explore independently. A typical Tuscan lunch, cheese tasting, and hotel pickup are included.

(8)

from $167

Private Montalcino and Pienza Tour from Siena

6 hoursFree Cancellation

4.0

(3)

from $556

Private Tour: Secret Siena Walking Tour

3 hoursFree Cancellation

⭐ Experience Highlights — What’s Included Visit to Our Historic Wine Estate- Discover an organic winery with over 300 years of heritage. ️ Chef-Prepared Three-Course Lunch - Featuring the truffles you found with fresh caprese salad, pasta, dessert, or cheese selections Truffle & Wine Pairing- Guided tasting of three organic estate wines selected by our chef & Sommelier. Free Time to Explore the Vineyards - Enjoy breathtaking views overlooking Siena.

(114)

from $333

Per group

Wine Tour & Tasting Lunch

You'll visit the winery’s production area and cellar, gaining an inside look at the winemaking process—from vine to bottle. The experience culminates with a guided tasting of the estate’s wines, right in the Poggio ai Laghi vineyard itself or at a nearby tasting spot, paired with a delicious lunch. Whether you're a wine lover or a curious traveler, this tour offers a rich and memorable experience rooted in tradition and flavor.

4.9

(11)

from $71

Lunch with Wine Tasting at Poggio ai Laghi Winery

Lunch with Wine Tasting at Poggio ai Laghi Winery

1 hour 45 minutesFree Cancellation

4.9

(8)

from $42

Cooking Class: Italian Authentic Recipes with Lunch

Want to get your hands dirty with dough? This is the cooking class experience for you! You will learn how to cook simple and delicious recipes with our Italian Chef to add a taste of Tuscany to your table while tasting our exclusive wines. After the cooking class, our wine expert will teach you the basic information for a wine tasting and will explain how wine permeates the culture of this territory. This is more than just a simple cooking class; it’s an experience that engages all your senses, leaving you with a deeper appreciation for the art of winemaking and the Tuscan cuisine. Whether you’re a wine connoisseur or a novice, this cooking class promises a memorable and enriching experience.

Cooking Class: Italian Authentic Recipes with Lunch

3 hoursFree Cancellation

4.7

(3)

from $92

Splendid Classic Siena Tour with guaranteed departure from Via di Città at 11am in English and at 12.15pm in Italian. An expert local Guide will introduce you, in an interesting and pleasant way, to the history of Siena, the Duomo, Piazza del Campo and other monuments of the city. We will talk about the Palio, the districts and visit the lesser known and quieter corners of the city. Including entrance ticket to the Duomo. In case of religious celebrations or extraordinary closures (such as Sunday morning for Mass), the visit will be moved to the Antico Ospedale di Santa Maria della Scala, still guaranteeing a complete experience.

Siena : Siena Guided Tour with Duomo or Museum

1 hourFree Cancellation

4.3

(45)

from $42

Travel off-road through the Chianti valley on this day-long Tuscan wine tour. As your guide drives a vintage SUV, you'll gaze out at the gentle green hills and grapevine groves that typify the landscape. Stop at a few wineries to sample several varietals of wine along with local products such as honey and olive oil, then relax over a traditional Tuscan picnic for lunch at your final stop.

Private Off Road Wine Tour in Chianti

6 hoursFree Cancellation

(23)

from $396

Wine Tasting with Cured Meats and Cheeses in Siena City Center

1 hourFree Cancellation

Private wine tour of Chianti

(4)

from $43

6 to 8 hoursFree Cancellation

4.6

(10)

from $476

Combine three of Italy’s most vital delights—wine, landscapes, and history—on this tour of the 15th-century Castello Tricerchi Montalcino wine estate. Exploring in a group no larger than 15, discover 600 years of history, including the chapel, the vineyards, and the cellars. Round off your visit with a tasting of three signature wines—Brunello di Montalcino, Rosso di Montalcino, and a Toscana IGP—paired with delicious local nibbles.

Historic Castle & Brunello Wine Experience in Montalcino

Historic Castle & Brunello Wine Experience in Montalcino

1 hourFree Cancellation

3.9

(36)

from $46

Private Grape stomping at Chianti Farmhouse

4 hoursFree Cancellation

4.9

(11)

from $380

PRIVATE TOUR: Full-Day Volterra & San Gimignano with Wine Tasting Experience

7 hoursFree Cancellation

(4)

from $298

- Immerse yourself in the world of Tuscan wine with our comprehensive tasting experience. - Master the art of tasting: Learn professional wine and extra virgin olive oil tasting techniques. - Discover Chianti's soul: Explore the region's rich wine culture, terroir, and the iconic Sangiovese grape. - Uncover the Super Tuscan legend: Understand the origins and evolution of this revolutionary wine style. - Savor exceptional wines: Taste our full range of organic wines, including an award-winning Super Tuscan and rare native grape varieties. - Guided by experts: Benefit from the knowledge of our certified wine guides. - Elevate your palate and expand your wine knowledge in an unforgettable wine and food experience.

MONTECHIARO Chianti & Supertuscan WINE EXPERIENCE

MONTECHIARO Chianti & Supertuscan WINE EXPERIENCE

1 hour 30 minutesFree Cancellation

Learn to cook traditional Italian dishes during this Tuscan cooking class in Siena. From homemade pastas to juicy cuts of meat, a professional chef leads you through a combination of family-favorite recipes and time-tested dishes, culminating with a shared meal and excellent wine. This class is held in a professional kitchen and limited to a small group of 15 people or fewer for a more intimate experience.

(5)

from $42

Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner

Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner

4 hoursFree Cancellation

Savor the flavors of Siena on this delightful food tour, where you’ll explore the culinary treasures of Tuscany. A local guide will lead you through the charming streets, sharing fascinating insights about the region’s food and wine culture. Enjoy tastings of sparkling wine, red wine, gelato, pecorino cheese, cured meats, pizza and traditional sweets like cantucci and panforte. This small group experience ensures an intimate atmosphere, perfect for food lovers looking to immerse themselves in authentic Tuscan cuisine. - 2 - hour walking food tour through Siena’s enchanting streets - Taste a variety of local Tuscan products - Learn about the history and culture of Siena’s culinary scene - Enjoy a small group setting for personalized attention from your guide

(352)

from $155

Siena Food Tour : Local Tuscan Flavors

Enjoy a wine experience in the heart of Val D'Orcia, surrounded by the most authentic Tuscan countryside. Together with Tatiana, the owner of Poggio del Moro, or our oenologists, you will explore the Poggio del Moro estate - from the vineyards, to the oil mill, to the cellar and the barrique cellar - and you will learn the production process of our natural wines, free from pesticides and unnecessary production interventions. Poggio del Moro is an out of the ordinary boutique winery, an extraordinary open-air art gallery. In addition to our excellent wines, here you will find contemporary art exhibitions or artistic performances, which you can observe while visiting the cellar or tasting your wine in relaxation, an absolutely original and refined experience in an intimate and exclusive setting!

(2)

from $106

2 Hours Visit and Wine Tasting with tastings in Val D'Orcia

2 Hours Visit and Wine Tasting with tastings in Val D'Orcia

What makes this experience truly unique is the opportunity to enjoy an authentic Tuscan dinner among the vineyards of Paradiso di Cacuci, surrounded by the peaceful atmosphere and timeless beauty of the Montalcino countryside. As the sun sets over the rolling hills, guests are guided by expert sommeliers through the vineyards and ageing cellar, discovering the passion and traditions behind Brunello di Montalcino. The evening continues with a curated tasting of exceptional Tuscan wines paired with traditional cuisine, creating a journey where every glass and every dish reflects the soul of Tuscany. From Brunello Riserva selections to handmade pasta and authentic Tuscan flavours, the experience combines elegance, intimacy and a true sense of place. Far from crowded restaurants and commercial tastings, this is a refined and immersive evening designed for those seeking exceptional wines, authentic food and the unforgettable atmosphere of a dinner in the vineyards under the Tuscan sky.

(55)

from $83

Montalcino: Brunello Wine Tasting & Tuscan Dinner

Montalcino: Brunello Wine Tasting & Tuscan Dinner

3 hoursFree Cancellation

The Chianti hills in Tuscany are known for their traditional Chianti Classico and modern Super Tuscan wines. Sample both in a single tasting and learn about their production and history with this winery tour and tasting. Visit a historic, family-run cellar just outside of Siena and sample the most recent vintage directly from the barrel, plus four Chianti and Super Tuscan wines during a guided sit-down tasting.

(5)

from $196

1 hour 30 minutesFree Cancellation

Wine & Cheese Experience

Spend a memorable day exploring Tuscany’s most famous landmarks and landscapes on a relaxed and well-balanced itinerary from Siena. Your journey begins with a comfortable transfer by air-conditioned coach through the rolling hills of the Tuscan countryside. Reach Pisa, where you will have free time to explore the stunning Piazza dei Miracoli, a UNESCO World Heritage Site. Admire the world-famous Leaning Tower, the Cathedral, and the Baptistery from the outside, and take your time capturing unforgettable photos. Continue your experience with a stop in the heart of Chianti, where you will enjoy a traditional Tuscan lunch paired with a guided wine tasting at a local winery. In the afternoon, arrive in San Gimignano, one of Tuscany’s best-preserved medieval towns. On the way back from Pisa, you’ll pass through Florence before returning to Siena. This allows for a smooth and well-organized route across Tuscany.

(3)

from $71

Likely to Sell Out

From Siena: Pisa and San Gimignano Day Trip

From Siena: Pisa and San Gimignano Day Trip

8 hoursFree Cancellation

4.0

(1)

from $94

Dinner with wine tasting at Poggio ai Laghi winery

A wine expert who will guide you through the tasting journey. Wine tasting that includes 2 Spumante and 3 Red Wines. Olive Oil tasting that includes Truffle, Chili Pepper, and Extra Virgin Olive oil. Aceto Balsamico tasting that includes Onion and Modena vinegars. Tuscan appetizers: Salame toscano, finocchiona, prosciutto crudo toscano, pecorino, bruschetta with fresh tomato and basil, cialda di pane tostato with Extra Virgin Olive Oil. First course: Penne al ragù or Penne al pomodoro. Second course: Arista with roasted potatoes. Dessert: Cantuccini and Vinsanto

Dinner with wine tasting at Poggio ai Laghi winery

See the top sights in Siena without the hassle of a guidebook or map with this small-group walking tour through the medieval old town. Join your local guide for a stroll along picturesque historic lanes to take in landmarks like the Piazza del Campo, Basilica of San Domenico, and Sanctuary of St. Catherine of Siena. Opt to add on a visit to the city’s magnificent Cathedral, rich in artworks by Renaissance masters.

(6)

from $67

Discover the Medieval Charm of Siena on a Private Walking Tour

2 to 3 hoursFree Cancellation

(262)

from $185

Inject a bit of adventure into your wine tasting experience with this ATV tour through the vineyard-covered countryside surrounding Siena. Take in views of the UNESCO-listed Crete Senesi landscape as you zip over the hills behind your guide, following unpaved trails through woods and fields. End at a family-run cellar to sample Tuscan wines paired with local gourmet specialties and snacks.

Wine Tasting ATV tour in Tuscan countryside

Wine Tasting ATV tour in Tuscan countryside

4 hoursFree Cancellation

4.7

(23)

from $381

Siena walking tour with lunch & Chianti wine

Take a tour of Siena with a local, and get the lowdown on the city that the guidebooks can’t give. In a small group, explore Siena by foot to discover the history behind the UNESCO-listed Piazza del Campo, the oldest bank in the world, and other monuments. You also have a chance to sample classic food and drinks from Tuscany such as Pecorino cheese, homemade pasta known as pici, the famous Chianti wine, and more.

Siena walking tour with lunch & Chianti wine

2 hours 30 minutesFree Cancellation

Siena’s Ultimate Food Tour: Full Tuscan Meal by Do Eat Better

(101)

from $101

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Top Attractions in Siena

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The magnificent Gothic and Romanesque structure of Siena Cathedral (Duomo).

Attractions

What are people saying about Siena

Melissa_A, Aug 2026

Highly recommended

Hands down one of the highlights of our trip! My dad and I took a food tour in Siena with Jacopo, and he was incredible. Jacopo is amazingly knowledgeable, sharing fascinating local history and culinary stories alongside delicious tastings. Be prepared for a bit of a walk—which was a great way to explore the town and burn off some of the food! I can't recommend Jacopo and this tour highly enough

Guided Winery Tour and Wine Tasting in Siena

WH_E, Aug 2026

This is Tuscany/Siena

Picture yourself in the heart of the Tuscany wine world and with this tour, you are there. Learned about how the grapes are nurtured in the vineyard, how they are processed in the cellar and most importantly how they can be enjoyed (5 tastings) when paired with great fresh food.

Siena: Chianti Sunset Tour with Dinner & Wine Tasting

Natalie_M, Jun 2026

A sensational evening to be had!

This experience was a highlight of our trip to Siena. Helene hosted our vineyard tour and chef-prepared, delicious 4 course dinner with generous paired wine tastings in excellent English, making the experience easy and very relaxed. The vineyard was easy to find and such a stunning and picturesque location, we felt we got great value for money and highly recommend.

Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner

Diana_S, Jun 2026

Excellent and highly recommended!

The class was very well organized, easy step-by-step processes for an outstanding 4 course meal (made by us)! We used all simple ingredients that are available everywhere so we can reproduce the recipes. Chef Francesco answered all questions with patience and great knowledge! It was one of the highlights of our trip! Highly recommended!

Siena Underground Wine tasting in a Medieval Cave

Kelley_D, Jun 2026

Must see cave and wine tasting in Siena !

Excellent wine tasting experience in a cave dating back to 700 BC. Federico is a knowledgeable and experienced sommelier and provided a comprehensive overview of brunellos and chiantis. We joined his wine club and are looking forward to enjoying Italian wine at home that you cannot get in the US!

Small-Group Montepulciano and Pienza Day Trip from Siena

Kim_H, May 2026

Great small group Day Tour

Great trip from the minute we started. Our driver/tour guide Juliana greeted us with a smile and off we went. Her knowledge of the area and her enthusiasm for all the locations we visited was outstanding. Perfect combination of sightseeing with frequent stops along the way. The “Farm to Table lunch was a highlight for sure. Highly recommend, you will not be disappointed.

Tuscany Hiking Tour from Siena Including Wine Tasting

Lynda_R, May 2026

Loved it!

A fantastic walk with a really lovely informative guide. Very easy hiking about 10km. Would suggest hiking boots/shoes has it has many stones on the trail. Wine tasting after was great, gorgeous place and the wine was spec. Ended up having lunch at the same place which was really yummy! Highly recommend, such a great way to see the rolling hills of Tuscany and get out of the crowds!

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

Robin_H, Apr 2026

Fabulous!!

Stunning drive to this beautiful, sun-soaked castle in Montalcino. Our hostess was so lovely and shared just the right amount of information. We enjoyed an amazing lunch paired with delicious wine—and couldn’t resist taking a couple bottles with us. Highly recommend this tour…we absolutely loved it.

Montalcino: Brunello Wine Tasting Experience

Lesa_H, Mar 2026

Great time!!!

Alice was very personable and took good care of us. She led us through the beautiful property giving us the historical background of the fortress, family and area, as well teaching us about Brunello wine and the winery. The tasting room was filled with old world antiques and decor. I felt I was in a castle! The wine and cheese were delicious, the other couple who joined us were lovely. We had a great time. Thank you Alice!!

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

Kevin_L, Feb 2026

The Perfect Tuscan experience!

Exactly what we were looking for! A unique experience-. Mattea was a colorful guide, fun and knowledgeable of the area and wines. A small self sustaining cheese farm with olive oil and wine. Pienza is a must see and finally a private wine tasting in montalcino.! Thanks Mattea for a great day!

Private Tour: Secret Siena Walking Tour

Jay_S, Oct 2025

Wonderful Tour, Great Guide!

Our tour guide, Giorgia, was very personable and knowledgeable. We learned a great deal about Siena and a short amount of time. A highlight was Giorgia's expertise regarding the Duomo pavement art. Truly fascinating. The pace of the tour was perfect and Giorgia walked the streets discussing it's history and views with patience.

Siena walking tour with lunch & Chianti wine

Chris_C, Oct 2025

Our tour guide Mohad was...

Our tour guide Mohad was incredibly knowledgeable, not only about Siena’s history but also about all the food, wine and gelato places. Some of them truly hidden gems! Perfect mix of walking tour and tasting of local specialties, all within 3 hours and away from the big tourist areas. I would highly recommend this tour!