Top Siena Wine Tasting Tours - page 4

From Siena: Pisa and San Gimignano Day Trip

8 hoursFree Cancellation

4.0

This customized day trip pairs the otherworldly landscapes of southern Tuscany with the region’s frozen-in-time villages and prized flavors. Relax and take in the views from a luxury vehicle while a private guide and driver handles the country roads. Taste famed Brunello wine in Montalcino and Pecorino cheese in lovely Pienza, visit a medieval monastery, and get hand-picked recommendations for an authentic Tuscan lunch.

from $92

Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

8 hours

(11)

from $674

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

What makes this experience truly unique is the intimate atmosphere of Paradiso di Cacuci, a family winery nestled among the rolling hills of Montalcino, far from crowded commercial wine tours. Guests are welcomed into an authentic Tuscan estate where tradition, landscape and passion come together to create a genuine Brunello experience. From walking through the vineyards to exploring the ageing cellar, every moment offers a deeper connection to the craftsmanship and philosophy behind Brunello di Montalcino. The guided tasting allows travelers to discover the elegance and evolution of Sangiovese through carefully selected wines, perfectly paired with traditional Tuscan flavours. Surrounded by breathtaking vineyard views and the peaceful atmosphere of the Tuscan countryside, this experience is designed for those seeking not only a wine tasting, but a refined and memorable journey into the heart of Tuscany.

4.7

(23)

from $372

Montalcino: Brunello Wine Tasting with Tuscan Specialities

Montalcino: Brunello Wine Tasting with Tuscan Specialities

1 hourFree Cancellation

4.7

(7)

from $87

Cooking class: become an Italian lasagna master

Enjoy your handmade meal with a tasting of Poggio ai Laghi wines, set in a working vineyard and traditional kitchen. As your lasagna bakes, you’ll enjoy a guided tasting of wines, and our wine expert will teach you the basic information for a wine tasting and will explain how wine permeates the culture of this territory. Once the meal is ready, sit down for a relaxed lunch or dinner overlooking the vineyard, and enjoy your freshly made lasagna alongside wine pairings. A light Tiramisu dessert can complete the experience. 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 foodie, a wine lover, or a curious traveler, this class is a flavorful journey into Tuscan tradition.

Cooking class: become an Italian lasagna master

3 hoursFree Cancellation

Home to medieval hilltop towns and fertile vineyards, Tuscany is widely considered the jewel in Italy’s crown. On this tour, visit the beautiful Tuscan towns of Pienza and Montepulciano, and enjoy a complete immersion in authentic Italian culture and cuisine. With travel from your Chianti or Siena hotel, sample local wines in historic cellars and savor a delicious lunch in a traditional Montepulciano winery.

from $89

Cities, Cheese and Wine Tour in Pienza & Montepulciano

Cities, Cheese and Wine Tour in Pienza & Montepulciano

6 to 8 hoursFree Cancellation

4.9

(27)

from $580

Finding wineries deep in the Chianti countryside is tricky for first-timers in the region. This experience removes the guesswork, taking you on a tour of the historic Montechiaro Estate. Enjoy tasting multiple Chianti and Supertuscan wines, including rare varietals from the Arteliquida project, paired with traditional Tuscan specialties from olive oil to artisan cheese. Ideal for foodies looking for an opportunity to sample local flavors.

Montechiaro VIP Wine Experience

2 hoursFree Cancellation

4.5

(2)

from $70

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

7 hoursFree Cancellation

(4)

from $290

Private Grape stomping at Chianti Farmhouse

4.9

(11)

from $371

Take off your shoes and - literally - immerse yourself into ancient Tuscan culture on a grape stomping excursion to the Chianti hills. In addition to grinding grapes into juice with your bare feet, you’ll also get an up close look at life at a Tuscan winery. A visit to the wine cellar and tasting is also included. After you’ve stomped to your heart’s content, replenish your strength with a homemade lunch.

Private Grape stomping in Chianti from Siena

Private Grape stomping in Chianti from Siena

5 hoursFree Cancellation

from $450

Get views you can't find anywhere else on this hot-air balloon ride over Tuscany. Starting in Siena, float above the countryside and take in scenic views of the low-rolling hills, some clad in grape vines, others crowned by a rustic ancient villa. Ascend as high as 2,000 feet (609 meters) and enjoy seeing the countryside and surrounding ancient villages and towns. Upon landing, enjoy a glass of sparkling wine to celebrate your experience.

Hot Air Balloon Flight Over Tuscany from Siena

Hot Air Balloon Flight Over Tuscany from Siena

3 hoursFree Cancellation

4.8

(141)

from $360

The Chianti Hills are a must-visit for wine lovers in Tuscany—and this small-group winery tour offers an immersive introduction to the region's vinous delights. Pick a start time that's best for you, make your own way to Castellina in Chianti, and explore a wine estate whose history dates back centuries. Then, enjoy a guided tasting of four premium wines, all paired with local olive oil, focaccia, cheese, and cured meats.

Chianti Classico wine Tour and Tasting

1 hour 30 minutesFree Cancellation

3.7

(27)

from $69

Explore Val d’Orcia, a UNESCO World Heritage site known for its stunning landscapes, art, and rich food traditions on this private tour. Visit Montalcino, home of the renowned Brunello wine, where you'll enjoy a guided winery tour and lunch. Then, head to Montepulciano, a medieval city with Renaissance palaces and sweeping valley views, famous for its Vino Nobile wine. Enjoy wine tastings in both towns while taking in their historical and scenic beauty.

Private Montalcino and Montepulciano Tour from Siena

7 to 8 hoursFree Cancellation

(2)

from $604

Val D'Orcia Wine and Heritage Tour

9 hoursFree Cancellation

Chianti Classico E-Bike Tour

from $238

5 to 6 hoursFree Cancellation

(25)

from $302

Become a pilgrim of sorts and take a scenic hike on the historic Via Francigena, an old pilgrimage route that stretched from Canterbury in England to Rome. The rural route takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Best of all, once you get to the medieval village of Monteriggioni you're rewarded with a wine tasting. At the end, head back to Siena via train.

Likely to Sell Out

Tuscany Hiking Tour from Siena Including Wine Tasting

Tuscany Hiking Tour from Siena Including Wine Tasting

Experience the delight of cruising through the Tuscan countryside aboard an original Piaggio Ape Calessino. Revel in the unique charm of Chianti's landscapes as you wind along peaceful roads, surrounded by the fragrant scents of the countryside and the gentle hum of farm life. Join our daily tour and immerse yourself in the heart of Tuscany's medieval villages, guided by our knowledgeable escorts. Pass through the Chianti hills, taking in the picturesque scenery at every turn. Your journey will culminate in a visit to a renowned winery, where you'll indulge in a wine tasting and a delightful light lunch.

4.9

(122)

from $70

Likely to Sell Out

Ape Calessino Tour through Tuscan Landscapes

Ape Calessino Tour through Tuscan Landscapes

from $127

Begin your day in the magical city of Florence, the Renaissance jewel. Marvel at the panoramic masterpiece from Piazzale Michelangelo, capturing the essence of this timeless city. Stroll through the historic center, a living canvas adorned with Palazzo Pitti, Ponte Vecchio, and Piazza della Signoria. Embark on a scenic drive through Chianti, where postcard-worthy landscapes of rolling hills and cypress-lined roads unfold. Trace the paths of ancient pilgrims, venturing through vineyards that breathe life into the iconic Chianti region. Farm Lunch: Indulge in a flavorful Tuscan feast at a charming farm, where Lasagna, Pecorino, and savory Ham are paired with the finest regional wines. Let the tastes of Tuscany enchant your palate. Afternoon Charms of San Gimignano: Discover the medieval enchantment of San Gimignano, a town adorned with towering structures that echo tales of history. Sample the world's best gelato as you explore the charming streets and absorb the town's timeless allure.

PRIVATE TOUR: Florence & Chianti in one day with Lunch and Tasting in Winery

PRIVATE TOUR: Florence & Chianti in one day with Lunch and Tasting in Winery

9 hoursFree Cancellation

(2)

from $290

Experience the culinary delights of the Chianti region on a half-day tour from Florence to a Tuscan farmhouse. Go in search of truffles with an expert guide and his trained dog during a 1-hour forest walk, then enjoy a traditional lunch that features the fresh truffles accompanied by extra virgin olive oil and Chianti Classico wine. Includes tastings of wine, olive oil, and honey, and a 3-course lunch.

Private Truffle Hunting in Chianti

5 hoursFree Cancellation

(5)

from $394

Private Ebike Tour in Chianti

6 hoursFree Cancellation

(4)

from $364

Explore the landscape of Tuscany on a private, full-day cycling tour from Siena. With the full attention of your guide, follow a route along the Via Francigena, an ancient pilgrimage route that once linked Canterbury to Rome and a popular destination for photographers. Rest and refuel after a day of activity with a three-course lunch and wine pairings at a Tuscan vineyard. Hotel pickup and drop-off is included.

Private E-bike tour in Chianti from Siena

Private E-bike tour in Chianti from Siena

6 hoursFree Cancellation

4.0

from $443

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s simple use as a vehicle. Ideal both on city’s tiny alleys and on the famous country-side windy roads. We will be visiting typical medieval villages, get in touch with local wine and food producers as well as artisans, and stop along the way to take some picturesque photos that will become indelible memories. An experienced tour guide will lead you around and show you the way as only a local can. The tour ends in a local farm where we will be hosted by a family that has been living there since centuries, producing their own wine, Chianti Classico. We will have the chance to visit the property including the cellar and then relax where a traditional Tuscan lunch will be served, all accompanied by their wines. Pick up and drop off from your accomodation in Siena included.

Private Vintage Fiat 500 tour in Chianti From Siena

5 hoursFree Cancellation

from $473

Explore Siena’s historical highlights and iconic cathedral on a private walking tour of the historic center. This short but comprehensive tour is designed for curious travelers who want to maximize their limited time in this Tuscan city. As you admire Piazza San Domenico, Torre del Mangia, and other local treasures, your guide will provide illuminating commentary that takes you out of the guidebook and into medieval Tuscany.

Siena Private Walking Tour: Traditions, Streets & Cathedral

Siena Private Walking Tour: Traditions, Streets & Cathedral

2 to 3 hoursFree Cancellation

4.5

(81)

from $179

Lunch in a Tuscan vineyard with wine tasting

2 hoursFree Cancellation

Siena Underground Wine tasting in a Medieval Cave

(5)

from $65

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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

Ronald_J, Jul 2026

One of our best wine tasting experiences.

This is amazing experience in which the owners discovered the cave by accident in a shop they purchased. All temperature controlled. Francesca and her husband are a devoted and very knowledgeable couple. Don't miss this wine tasting experience and history of the Tuscan wine region specifically in Siena.

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

Jonathan_G, Jun 2026

10th Anniversary Trip

Was so pleased with this experience. The chef, Francesco (and translator) were both so patient, explaining everything and going at a pace that everyone could learn. The food was AMAZING, and the techniques taught will be able to be used back home. Highly recommend for a relaxing and delicious meal!

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

Mary_C, May 2026

Sandra was amazing! We...

Sandra was amazing! We learned so much about the city and the food and wine of the area. The places Sandra choose for the food and wine experience were all delicious and nice size portions. We enjoyed every minute of the tour and would highly recommend,

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.

Siena: Chianti Sunset Tour with Dinner & Wine Tasting

Linda_G, May 2026

Highly recommend the charming family winery.

Lovely family winery. Very knowledgeable, friendly, and accommodating staff. Amazing they produce over 100,000 bottles a year. Hope I got that right. Only 20 minutes from Siena. Their bottle labels designed by an artist are works of art. If you are in the area recommend visiting this charming winery.

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.

Private Tour: Secret Siena Walking Tour

Susan_Y, Apr 2026

The absolute best! Must do!

This was probably one of the best tours we've been on. Georgia, our guide, was so much a great guide. She was very in tune with us too, knowing when she had to slow down her talking for my older mother who was not understanding and when to speed it up. She customized our tour with us and gave us so much history and lore, we fell instantly with Siena because of her. 10/10 best thing to do in Siena. Highly recommended!

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!!

Hot Air Balloon Flight Over Tuscany from Siena

Marita_L, Oct 2025

Absolutely an experience not to miss

They do a great job in making sure that the flight will be safe, gauging the weather and letting you know if it has to be canceled or moved to a new location. While a new location can be inconvenient it is for your safety. I appreciate the care they take. The experience was extraordinary. The staff was very helpful and they treat you with kindness and respect.

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!