Top Tuscany Wine Tasting Tours - page 42

Tuscany & Umbria-food and wine tour: flavors of Italy’s heartland

5.0

(1)

10 hoursFree Cancellation

from $383

Get ready to discover a unique romantic Dolce Vita experience! Begin your unforgettable journey in the heart of Tuscany with the elegance and performance of a Maserati Ghibli. Enjoy a smooth ride through the picturesque Tuscan countryside with your private driver, starting from Florence. Visit a panoramic viewpoint in Impruneta, the Abbazia di Colti Buono winery for an exclusive wine tasting, and have a sumptuous lunch at the historic Castello di Vicchiomaggio. On the return trip, travel along the scenic Via Chiantigiana, offering picturesque views of rolling hills, vineyards, olive groves, and charming medieval villages. This tour blends luxury, culture, and culinary delights for a truly memorable experience in Tuscany.

Exclusive Dolce Vita Maserati Tour

931

6 hours 30 minutesFree Cancellation

from $764

Discover Tuscany like never before. Reach Chianti Rufina in the Florentine countryside in a simple and sustainable way by taking the train to Sieci, where you’ll be welcomed and transferred directly to the estate—no car needed, just a seamless and eco-friendly journey into the heart of Tuscany. Upon arrival, the adventure begins. Hop on your Trotter and glide through vineyard rows and the countryside, surrounded by the authentic scents of Tuscany. This fun and immersive experience blends nature, wine, and breathtaking views—perfect for travelers who love the outdoors and want to explore it in a unique way. The experience ends with a relaxing lunch featuring traditional Tuscan dishes, paired with a wine tasting where you can savor the true magic of Chianti Rufina and the authentic character of this remarkable land.

Sustainable Tuscany E-Scooter Ride, Wine Tasting & Lunch

442

5 hours

from $144

Special Offer

We are a small family-run winery, in the heart of Tuscany, certified organic. Every bottle we produce comes exclusively from grapes, cultivated with deep respect for the land and for those who live there. We welcome you for a private tasting of 3 or 5 wines, accompanied by a visit to the barrique and wine cellar : a sensory journey through the scents of wood, the silence of the barrels and the secrets of the production process In tasting you can discover the IGT in purity, authentic expression of the great international vines interpreted with Tuscan soul : Merlot — enveloping, elegant, with notes of ripe red fruit and a long, silky finish Cabernet Sauvignon — structured and complex, with hints of cassis, spices and noble tannins Syrah — intense and enveloping, with spicy character, notes of black pepper and dark fruits All accompanied by a rich platter of cold cuts and cheeses and a basket of bread.

Super Tuscan Wine Tour by Carus Vini

1 hourFree Cancellation

from

$24

$30

Discover Montepulciano and Chianti areas by tasting various vintages and have lunch with a breathtaking view with transfer from Florence. You will visit a historic cellar in the very heart of Montepulciano old centre, taking a guided tour of an underground cellar, where you will encounter oak barrels of various sizes, small fountains, some authentic Etruscan tombs, various workshops and ancient wells. After a brief photo stop in Bagno Vignoni, you will proceed to the Chianti wine area, admiring the real Tuscan atmosphere of olive groves, vineyards and rolling hills in the countryside. You will visit a family-run winery in the very heart of Chianti Classico, after the tour you'll have lunch to enjoy local cuisine with dishes prepared only with high-quality products that tell the story of the flavors and aromas of Tuscan tradition. Visit of a second winery on the way back to Florence. Private transfer is available from Florence.

Florence: Montepulciano and Chianti in 1 day + lunch&transfer

8 hours 30 minutesFree Cancellation

from $847

Step into the rustic charm of Orcia Valley during a guided tour of a local dairy farm. Immerse yourself in the daily life of a modern-day peasant as you meet animals, from donkeys to sheep, each playing a vital role on the farm. Then, journey into the heart of cheese-making as we unveil the secrets behind our artisanal cheeses. Indulge your taste buds with a delightful cheese tasting, perfectly paired with local wine. But the adventure doesn't end there! Dive into the culinary delights of Tuscany with a hands-on cooking class at a traditional Tuscan farm. Under the guidance of our expert chef, learn the art of preparing classic Italian dishes from scratch. After, savor your creations, accompanied by local wine. Next, embark on a journey to the renowned Chianti Classico wine region, where history and legend await at a prestigious historic cellar. Explore the ancient rock-carved winery, where tradition meets innovation, and indulge in a wine tasting featuring their finest vintages.

Florence: Chianti Wine, Cheese Farm Day Tour &Pasta Cooking class

8 hours 30 minutes

from $913

Explore and Savor 3 Exquisite Wines at Tenuta Bossi

Welcome to our private and exclusive tour to discover Tuscany aboard a Fiat 500, the iconic Italian car! You will explore hidden medieval villages, where time seems to have stopped, and we will leave you free time to stroll through the cobbled streets and discover authentic local traditions. The tour begins with the reservation of your vintage Fiat 500, an iconic Italian car, which will make you feel like protagonists of a period film as you travel through the evocative Tuscan landscapes. You will make a stop in a historic cellar, where you can taste some of the best Tuscan wines produced in the region. After the tasting, you will continue to San Gimignano, a charming medieval village famous for its well-preserved medieval towers. You can walk through the cobbled streets and admire the historic architecture of this unique place in the world.

from $32

Chianti - Fresh Pasta, Sauces & Tiramisu Class only Small Groups

4 hours

from $144

Embark on a unique day-long journey with our "Exploration of Bolgheri Wines from Livorno" tour, immersing you in the world-renowned wine region of Bolgheri, famous for its exquisite Supertuscan wines. Starting from the port of Livorno, this exclusive tour combines world-class wine tastings with breathtaking landscapes and rich vinicultural history. Your adventure begins comfortably in a private minivan, departing Livorno for the rolling Tuscan countryside. Bolgheri, with its lush vineyards bathed in Tuscan sunlight, welcomes you into a world where winemaking is an art perfected over centuries. Spend your morning at a prestigious local winery, indulging in a selection of local wines, including the famed Supertuscan. These wines, a masterful blend of local and international grapes, are known for their robust and rich flavors, delighting the palate. Enjoy free time for lunch, choosing from various local restaurants to taste traditional Tuscan dishes paired with local wines.

Day of Tastings in the Land of Super Tuscans from Lucca

from $901

Your adventure begins comfortably in a private minivan, departing Livorno port. Bolgheri, with its lush vineyards bathed in Tuscan sunlight, welcomes you into a world where winemaking is an art perfected over centuries. Spend your morning at a prestigious local winery, indulging in a selection of local wines, including the famed Supertuscan. These wines, a masterful blend of local and international grapes, are known for their robust and rich flavors, delighting the palate. After the tasting, visit Bolgheri, a village enchanting with its cobblestone streets and ancient stone houses. Enjoy free time for lunch, choosing from various local restaurants to taste traditional Tuscan dishes paired with local wines. In the afternoon, another renowned Bolgheri winery visit awaits, enriching your wine tasting experience and aging processes that make Bolgheri wines so special. Your flavorful journey through Bolgheri's tastes and traditions concludes with a return to Livorno by 5:00 PM.

Day of Tastings in the Land of Super Tuscans from Livorno

Take a real sip of Tuscany's chill and calm countryside and escape the busy pace of Rome. Come and savor the very best of the Tuscan countryside—its flavors, stories, and breathtaking views. Exclusive & Intimate: Small-group experiences (max 7 per guide) ensure personalized attention and genuine local interactions. Unforgettable eBike Rides: Explore ancient paths, scenic vineyards, and breathtaking landscapes on high-performance pedal-assist bikes. Culinary Immersion: Savor authentic Tuscan flavors through unique dining experiences—from a hillside cheese house picnic to a hands-on cooking class and intimate restaurant dinners. Cultural Insights: Engage with local experts who unveil the hidden stories and history of this iconic destination. Book now for a once-in-a-lifetime adventure through Tuscany—a journey that delights your senses and nourishes your soul! Contact Us: For more detailed information or to receive a discount code for your booking, please contact us before booking.

from $1,538

Per group

Tuscany Multi day eBike tour Wine and Pasta

186

4 daysFree Cancellation

from $2,956

Take a real sip of Tuscany's chill and calm countryside and escape the busy pace of Florence. Come and savor the very best of the Tuscan countryside—its flavors, stories, and breathtaking views. Exclusive & Intimate: Small-group experiences (max 7 per guide) ensure personalized attention and genuine local interactions. Unforgettable eBike Rides: Explore ancient paths, scenic vineyards, and breathtaking landscapes on high-performance pedal-assist bikes. Culinary Immersion: Savor authentic Tuscan flavors through unique dining experiences—from a hillside cheese house picnic to a hands-on cooking class and intimate restaurant dinners. Cultural Insights: Engage with local experts who unveil the hidden stories and history of this iconic destination. Book now for a once-in-a-lifetime adventure through Tuscany—a journey that delights your senses and nourishes your soul! Contact Us: For more detailed info or to receive a discount code for your booking, please contact us before booking.

Escape from Florence to Cortona: 5-Star Hotel, Tours, Activities

186

4 daysFree Cancellation

from $2,956

Explore the stunning Carrara mountains, renowned for their exquisite marble quarries on a private tour. Discover the fascinating history and artistry behind marble excavation while touching real marble blocks. Afterward, relax in the charming village of Colonnata, where quarrymen have lived for over 2000 years. Enjoy a delightful aperitivo featuring cold cuts and wine, all while taking in breathtaking views of the quarries at sunset.

Private Tour of Carrara Marble Quarries with Aperitivo at Sunset

2 hours 30 minutesFree Cancellation

from $348

Per group

Explore the picturesque landscapes of Tuscany on a captivating day trip from Florence. This intimate journey invites you to savor the rich flavors of Brunello wine at a historic Montalcino estate, enjoy a delightful farm-to-table lunch with stunning views over Val d'Orcia, and stroll through the Renaissance gem of Pienza. With opportunities to taste award-winning pecorino cheese and extra virgin olive oil, this tour offers a deep dive into the heart of Tuscany's culinary traditions and breathtaking scenery. - Private wine tasting at a historic vineyard in Montalcino - Seasonal Tuscan lunch with panoramic views - Visit the UNESCO-listed town of Pienza for local flavors - Expert guide and private transportation included

Tuscany Private Guided Wine Tasting Tour by Car

10 hoursFree Cancellation

from $1,911

Per group

Likely to Sell Out

Indulge your sweet tooth with a hands-on dessert cooking class in the heart of Tuscany with our Italian Chef to add a taste of Tuscany while tasting our exclusive wines. You'll whip, layer, and taste your way through the traditional recipe using fresh, local ingredients—eggs, mascarpone, espresso, and more. Whether you're a beginner, this class is easy, fun, and perfect for all ages. While your dessert sets, relax with a glass while tasting our exclusive wines. This experience is all about sweet memories and delicious bites. You'll leave with a full heart, full belly, and the recipe to recreate your tiramisu anytime. 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.

Cooking Class: Dessert & Tuscan Wine Tasting

5.0

(1)

3 hoursFree Cancellation

from $76

3.7

(3)

Tuscan Wine Tasting and Local Cheeses

A deeper and more refined tasting in the heart of San Gimignano. Surrounded by vineyards and just minutes from the historic center, this experience offers an immersive journey into the most prestigious expressions of Poggio ai Laghi. What makes it special: Elegant setting among the Tuscan hills Guided tasting of 5 wines, including Chianti Classico and Supertuscan Exclusive selection featuring 100% Sangiovese and Merlot wines Premium olive oils and balsamic vinegars Traditional Tuscan food pairing with local specialties Dessert with Vin Santo for a complete experience A richer and more structured tasting, perfect for those who want to explore the depth and character of Tuscan wines.

from $43

Likely to Sell Out

The Noble Cellar Wine tasting in San Gimignano

108

A hands-on cooking class in the heart of San Gimignano. Step into the kitchen and experience Tuscany through its most authentic tradition: cooking, sharing, and tasting what you create. What makes it special: Interactive cooking class where you prepare the full menu Learn authentic Tuscan recipes and techniques step by step Guided tasting of 6 wines, including Chianti Classico and Riserva Selection of olive oils and balsamic vinegars Enjoy the dishes you’ve prepared in a relaxed, convivial setting A fully immersive experience, perfect for those who want to live Tuscany with their own hands, from preparation to tasting.

from $72

Likely to Sell Out

San Gimignano From Hands to Table Cooking class

108

3 hoursFree Cancellation

from $168

The winetasting is included in the price. Exclusivity: exclusive service in top-of-the-range Mercedes-Benz Business Van. This type of excursion is ONLY present in our catalog as we believe in the capabilities of our land away from the chaos of cities, where everything is still moving slowly. Here you will have the certainty of living the TRUE Italian life. Pasta, bread, wine and more cheeses, oil and cold cuts and the stop at the bar for a coffee will make sure that your taste buds will go crazy! Local: English-speaking driver, with deep knowledge of the territory. Our strength: maximum punctuality and absolute safety to respect the ship's schedules. Flexibility: Possibility to customize the excursion (country-side, winery, Florence). Experience: previous experience in the sector, present on the market since 2016. The chosen wineries are out of sightseeing.

Private Tour Pisa, countryside with wine tasting

5.0

(1)

from $467

Exclusivity: exclusive service in a top of the range Mercedes-Benz Business Van and transport with UTV as passengers. This type of excursion is ONLY present in our catalog because we believe in the capabilities of our land far from the chaos of the cities, where everything still moves slowly. Here you will have the certainty of living the REAL Italian life. Pasta, bread, wine and even cheeses, oil and cured meats and the stop at the bar for a coffee will make sure that your taste buds will go crazy! Local: English speaking driver, with deep knowledge of the territory. Our strong point: maximum punctuality and absolute certainty of returning on time. Flexibility: Possibility to customize the excursion (do the entire tour with a Van and air conditioning, avoiding dirt roads). Experience: previous experience in the sector, present on the market since 2016. The chosen wineries and the places are outside the classic tourist tours. The cost of the wine-tasting, is not included, varies from €35 to €50 per person.

Pisa E winery through the Pisan hills aboard a UTV

from $360

Guess the wine: Taste and have fun with whoever you want!

Wines according to an Expert

from $180

1 hourFree Cancellation

from $71

Who we are: Enoteca Alessi since 1952 "Entering Enoteca Alessi means crossing the threshold of wine history in Florence. Since 1952, our family has passionately guarded the secrets of the best Tuscan terroirs. We are not only a wine shop, but a historic shop where time seems to have stopped to leave room for the scents of good wine and authentic food. Here, among our wooden shelves and underground cellars, we select every day the best of Tuscan 'companatico', treating every bottle and every cheese shape with the respect that is due to a work of art. Come and visit us to live an experience that smells of home, tradition and 70 years of pursuit of excellence."

Tuscany Authentic Wine Bread and Companatico

1 hour 45 minutesFree Cancellation

from $82

You will be welcome in a familiar, informal and warm ambience of an historical building from the 17th century with all the modern comforts. The location is peaceful and perfect for recharging your batteries and for making your creative aspect come out. You are in an unspoiled area perfect for every activity in nature in your free time. Learn how to cook from scratch: the food used in the cooking course is outstanding, always fresh, local and high quality ingredients. Italian dishes are characterized by its simplicity and this makes the course ideal for entry level to more expert students. Besides all of this your teacher is not only passionate about Italian cuisine but also a wine expert and he will always match the food with the most appropriate wine.

3 Days Wine and Cooking Class in Tuscany

3 days

from $709

Full Day Tour to Val d'Orcia and Gladiator's Fields with Wines

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Top Attractions in Tuscany

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What are people saying about Tuscany

MICHELLE_T, May 2026

Exceptional Experience

Excellent tour! Exceeded our expectations!!! Cecilia was a wonderful guide, provided lots of background information and did it in three languages!!! The scenery is amazing and the villages are each unique. Our lunch took too long in Pienza, so I’d say go with something simple so that you don’t spend all of your time eating (but the food was delicioso!!!). There’s quite a bit of walking and the last tour has a steep climb up from the parking area to the village square and then down many steps to the winery (but it’s very cool!). The Tuscan countryside doesn’t disappoint although it’s hard to do it justice with a phone camera. Tour is great value for the money! So very happy we did it!!!

Half-Day Chianti Wine Tasting from Florence with Two Wineries

madalyn_h, Apr 2026

You’ll love this tour !

Visits to 2 different vineyards, and though different, each is beautiful and special. The tours are interesting and informative. The wines are gorgeous and each place provides Tod bits to eat with the wine. Perfect pairings! Our guide, Maria Louisa was off the charts knowledgeable and also very generous with her time, answering questions and helpful

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.

Lucca: Wine Tasting Experience - Tenuta Adamo Winery

Jenny_W, Apr 2026

Great experience! just plan your transport carefully.

Great wine tasting experience in a beautiful setting. David our host was very friendly and knowledgable. The only down side it was over €30 in a taxi to get there from Lucca because of this we planned to get a bus back but the next one was a 40min wait so we ended up getting a taxi back too. Possibly our fault for not planning better but something to bear in mind .

Half day Chianti Vineyard Escape from Florence with Wine Tastings

Lori_Q, Apr 2026

Wine tour

It was very nice. The tour guide told stories about the area while driving. It was an hour and a half ride out but she only talked at the beginning giving people time to enjoy a quiet ride. The wine locations were very nice. The host at Grace winery did a fantastic job telling about the vineyards and wine business. And I loved the set up in both locations where they did the tastings.

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!!

Chianti Vespa Tour with Tuscan Lunch or Dinner from Florence

Christina_H, Jan 2026

Our favorite day of the whole trip!

My boyfriend and I booked the Topolino for what ended up being a rainy November day. It also ended up being just us two, so Francesco alone led our tour and it was phenomenal, even in the rain! Francesco is so kind and engaging and showed us some really amazing spots but also left time for us to explore on our own! After dropping off our vehicles, we ended the tour with the wine & olive oil tasting (and bought some for home) and lunch was a delicious pasta and dessert pastry. All in all, the sights were gorgeous, the driving was fun, and the food was great. Cannot recommend enough!

Hidden Castles & Chianti Wine Experience– Small Group

Christina_P, Nov 2025

Great guided experience with Luca

Our guide Luca was very knowledgeable and gave great information all day throughout the tour. He had good recommendations for restaurants in the cities we visited, and explained the different wines and products very well. The tour itself was nice, with visits to two wineries and some cities with impressive views over the hillside in Tuscany.

Wine Experience In Chianti Hills from Florence

Andy_N, Nov 2025

Lovely wine tour!

We had a fab time tasting wines and Balsamic in the hills of Tuscany! Our tour guide was helpful and knowledgeable about the areas we visited and the wines etc we had were very good too. The Balsamic we tried on our first stop was the best I’ve ever had and bought a couple of bottles!! Would definitely recommend this tour although my one criticism would be to be a little more descriptive about the meeting point please… if you’re not from Florence, finding the actual ticket counter was a pain and we thought we were going to miss our trip… it’s right in the centre of the train station in a ticket hall around a corner so we found that difficult to find with the instructions online..

Tasting Tour in One of The Most Beautiful Cellars in the World

Jekaterina_S, Sep 2025

Great wine tasting in the heart of Montepulciano!

It was super interesting, the guide was great, the wine tasting was lovely, and it was definitely worth going! Keep in mind there are quite a few stairs, but nothing too extreme. You will also be on your feet almost the whole time, apart from the tasting.

Montepulciano: Winery Tour & Tasting Experience

Ken_S, Jul 2025

Great wine... interesting...

Great wine... interesting tour and loved walking into the caves... Guide was very informative and answered lots of questions from the group! Be prepared for a lot of stairs but it's well worth it!! Make sure to take pictures in the beginning and in the cave as you end up in a wine tasting room that is not very photo friendly!