Top Tuscany Wine Tasting Tours - page 43

Wine and Dine in Chianti Classico Exclusive Private Dinner

1 hour 30 minutesFree Cancellation

from $299

Picnic in vineyards with Bottle of Rosso di Montalcino

Explore the charming medieval town of San Gimignano, known for its iconic towers and rich history. After soaking in the sights, savor a delightful lunch at the Torciano estate, where you can also enjoy a guided tour of the winery and taste exquisite wines. The journey continues to Siena, a city filled with stunning architecture and vibrant culture. Ideal for travelers looking to immerse themselves in Tuscany's beauty and flavors. - Visit the enchanting town of San Gimignano, famous for its towers - Enjoy a delicious lunch and wine tasting at the Torciano estate - Experience the rich culture and stunning sights of Siena - Perfect for wine lovers and cultural enthusiasts alike

from $71

Pisa o Livorno to San Gimignano and Siena Tour &Wine Tasting

7 to 9 hoursFree Cancellation

from $657

Price varies by group size

The tour takes place in a historic company, among the first to be part of the Consorzio del Brunello di Montalcino, the company was founded in 1950 by Silvio Nardi, an Umbrian producer of agricultural machinery, who had fallen in love with the Tenuta di Casale del Bosco during his numerous visits to Montalcino. In 1958 the first bottle of Brunello under the Casale del Bosco brand was marketed, the company has maintained a long history of tradition over the years, demonstrated by the fact that for over 70 years the Nardi family has continued to manage everything. The villa is also a perfectly preserved witness to the past history of the area.

The Private Challenge of the Crus

1 hour 30 minutesFree Cancellation

from $90

Tuscany is one of the great food and wine destinations of Italy, and, indeed the world. The scenery is unbelievably beautiful with large tracts of agricultural land, including wheat fields, vineyards and olive groves, placed on rolling hills, dotted with cypress trees and criss-crossed by white gravel roads. So just imagine this: An unforgettable week in southern Tuscany, tasting some exceptional wines, learning how to cook like an Italian, visiting some spectacular medieval towns and enjoying sumptuous gourmet meals. All while staying in luxurious accommodation in the beautiful Val d'Orcia World Heritage area while in the company of other like minded people. Our Food & Wine Experiences are unique as they consist of small groups ensuring a more personalised and intimate experience.

8 Days Tuscan Food and Wine Experience Shared Tour

8 days

from $5,269

A tour where you can appreciate the beauty of the Umbrian High Tiber and its traditions. You will have at your disposal brand new e-bikes with which it will be possible to reach in the same tour the medieval villages of Citerna and Anghiari. A licensed National Guide will lead the tour in Italian or English presenting the most interesting aspects of the historical and natural heritage of the valley. We will cross the historic center of Citta' di Castello to follow the pleasant cycle path of the Tiber river until we reach Citerna. After a short visit we will resume the route to Anghiari.

Tour in and bike in Alta Umbria - Citerna and Anghiari

4 to 5 hoursFree Cancellation

from $156

Ideal for wine lovers seeking an authentic and intimate journey, the wine tour in Carmignano unveils one of Tuscany’s best-kept secrets. Far from the crowds, this experience offers a rare opportunity to explore a historic yet overlooked wine region, where winemaking dates back to the Medici era. Discover how tradition and innovation coexist in Carmignano, from artisanal biodynamic vineyards to cutting-edge cellars producing some of the most elegant wines in Tuscany. More than just a tasting tour, this experience connects you with passionate winemakers, immerses you in the region’s rich history, and showcases the true essence of Tuscany—untouched landscapes, farm-to-table hospitality, and world-class wines. Whether you’re an experienced connoisseur or simply looking for a unique, off-the-beaten-path adventure, this tour offers an unforgettable glimpse into the heart of Italian winemaking.

Carmignano Wine Tour with a Somm Small Group

(2)

7 hoursFree Cancellation

from $239

Discover the essence of Tuscany with a wine tasting and guided estate tour in Bolgheri, near Castagneto Carducci. Enjoy a warm welcome at a family-run winery surrounded by Cabernet Franc vineyards, where you’ll explore the estate, visit the cellar, and taste locally produced wines. Choose between two curated tasting experiences featuring fine Tuscan wines paired with regional specialties—perfect for both wine lovers and curious travelers seeking authenticity, tradition, and stunning vineyard views.

Wine Tasting and Estate Tour in Bolgheri

1 hourFree Cancellation

from $72

From Florence Brunello di Montalcino Wine Tour with Lunch

5 hoursFree Cancellation

from $268

Come and discover our farm in Montespertoli, where authenticity and sustainability meet. Immerse yourself in the breathtaking landscapes of Tuscany and live a unique experience, exploring our organic vineyards and participating in personalized tours and guided tastings. Discover our wine tradition and relax in a place where nature and wellness blend perfectly. An unforgettable experience awaits you!

Guided tour and tasting at Fattoria La Leccia

Painting and Wine Tasting Experience in Tuscany

from $42

3 hoursFree Cancellation

from $150

The perfect experience to immerse yourself in the most authentic Tuscany, the one made of passion, aromas and intense flavors. The visit and technical tasting of the four wines is followed by a cutting board with cold cuts and specialties from the Poggio Stenti company, a rich selection of typical Tuscan products of the highest quality. Tasting of four wines representative of the estate: Sangiovese Rosato – Maremma Toscana DOC (BIO) Vermentino – Maremma Toscana DOC (BIO) Montecucco Rosso DOC Tribulo – Montecucco Sangiovese DOCG

Wine and Specialties in Tuscany with Small Artisan Producer

Winery tour with panoramic aperitif in Chianti

from $54

2 hours 30 minutesFree Cancellation

from $42

Winery tour and tasting in the Chianti hills

3 hoursFree Cancellation

from $72

Le Bèrne Vino Nobile Wine Tour and Tasting in Montepulciano

1 hour 30 minutesFree Cancellation

from $42

Here are some aspects that make a Tuscany and Chianti wine tour unique: # Authentic Tuscan Experience - *Scenic drives*: Take in the breathtaking views of the Tuscan countryside, with its rolling hills, charming villages, and vineyards. - *Local cuisine*: Savor traditional Tuscan dishes, made with fresh, locally-sourced ingredients. - *Cultural insights*: Learn about the history, traditions, and customs of Tuscany and its people. # Expert Guidance - *Knowledgeable guides*: Enjoy the expertise of local guides who are passionate about Tuscan wine, history, and culture. - *Personalized attention*: Receive personalized attention and guidance throughout the tour. # Small-Group Tours - *Intimate group sizes*: Join a small group of like-minded travelers, ensuring a more personalized and immersive experience This unique combination of immersive wine experiences, authentic Tuscan culture, expert guidance, and unique activities makes for an unforgettable Tuscany and Chianti wine tour.

Tuscany and Chianti Wine Tasting Small Group Tour

8 hoursFree Cancellation

from $216

Immerse yourself in the culinary traditions of Tuscany with a practical lesson dedicated to the preparation of focaccia. Learn to knead the ancient 'Bico', a treasure of Tuscan bakery, under the Guide of Letizia, passionate cook and guardian of local recipes. Enjoy your freshly baked bico accompanied by a selection of Tuscan cold cuts and fine wines. This delightful journey ends with cantucci to dip in Vin Santo : the perfect ending for an unforgettable dining experience in Letizia's cozy home

Bico and Gran Tagliere the ancient Tuscan focaccia

My name is Valentina, as a local chef and sommelier I will be happy to guide you through the Italian and Tuscan flavors, in the comfort of your holiday home. I combine traditional Italian recipes, passion for local and organic ingredients and wine tasting; creating a unique fusion. You will learn the secrets and recipes to create authentic Italian dishes, see the preparations in the kitchen and learn about the ingredients, wine and territory. I will buy all the ingredients from the local producers I trust and I will get to you in advance to arrange everything and set the table. Relax with your loved ones and enjoy an exclusive experience in the privacy of your own holiday home. I will take care of you and the kitchen.

from $67

My name is Valentina and I am excited to guide you through Italian flavors with my cooking. Let me take care of you and your loved ones.

Fresh Pasta and Typical Dinner at Home

2 hours 30 minutesFree Cancellation

from $180

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

Siena Food Tour : Local Tuscan Flavors

Guided small group tasting in the countryside of San Gimignano, designed for those who want to understand Tuscan wine in a simple and authentic way. The experience is conducted by a local sommelier and combines tasting of wines representative of the territory with an accessible story about vines, landscape and traditions. Ideal for those visiting San Gimignano and looking for a relaxed, convivial and cultural moment, away from standardized tastings and crowded settings.

from $107

San Gimignano wine tasting Essence Tuscany

1 hourFree Cancellation

from $46

Discover the heart of Chianti on this private 7-hour tour filled with wine and history. Visit a family-owned winery for an insightful guided tour of the vineyard and cellar, where you’ll learn about traditional wine production methods. Enjoy a delightful wine tasting featuring the iconic Chianti Classico and a traditional Tuscan lunch made with local ingredients **Lunch is not included in the tour price, an additional €60 per person will be charged from the winery** Explore charming medieval villages like Greve,Castellina, and Panzano, each offering stunning views and rich cultural heritage. This tour is perfect for wine enthusiasts and history lovers alike, providing an intimate experience of the beautiful Chianti region. - 7-hour private tour exploring Chianti's wineries and villages - Guided tour of a family-owned winery with wine tasting and a traditional Tuscan Lunch**not included in the price** - Visit picturesque villages with rich history and incredible views

Private 7 Hour Chianti Tour Wineries and Medieval Villages

7 hoursFree Cancellation

from $718

Per group

Discover the charm, history, and flavors of Tuscany on this private full-day tour by luxury minivan, led by a licensed English-speaking driver-guide with deep local knowledge. Visit two UNESCO World Heritage sites—Siena, with its stunning Gothic cathedral and famous Piazza del Campo, and San Gimignano, known for its medieval towers and artisan shops. Enhance your experience with an optional wine tasting and full Tuscan lunch at a family-run winery (not included, but highly recommended). Enjoy a fully customizable itinerary with convenient pickup and drop-off from your accommodation in Florence. Highlights: -Private full-day tour for up to 7 travelers -Explore Siena and San Gimignano, both UNESCO World Heritage Sites -Travel in comfort with a luxury minivan with Wi-Fi and licensed English-speaking driver-guide -Optional wine tasting and lunch at a local winery (not included, but highly recommended) -Hassle-free pickup and drop-off from Florence

Private Full Day Tour Siena and San Gimignano with Wine Tasting

8 hoursFree Cancellation

from $898

Per group

Special Offer

This experience stands out because it combines, in a single activity, three authentic elements of Tuscany: a historic castle in the heart of Chianti, a gourmet tasting and a ceramics workshop. Unlike the classic wine tastings, here the participants are not only spectators, but protagonists: in addition to visiting the Castello Sonnino and tasting selected wines, they can create and decorate by hand their ceramic object with Ceramiche Corsini, a historic reality active since 1957. The value of the experience lies precisely in this exclusive combination of culture, taste and creativity, which allows you to experience Tuscany in an authentic way and bring home a unique and personal memory.

Chianti Wine Experience at Sonnino Castle Ceramics by Corsini

5 hoursFree Cancellation

from

$198

$216

Immerse yourself in the heart of Tuscany with a hands-on cooking class that brings farm-fresh ingredients directly to your table. Guided by expert instructors, you'll learn to craft handmade pasta, prepare a rich aglione sauce, and create a delightful fruit tart using homemade preserves. Each step is carefully explained, making it accessible for all skill levels. Enjoy the fruits of your labor with a lunch featuring local delicacies and a tasting of five exquisite wines. This is more than just cooking; it's about savoring the authentic flavors and traditions of Tuscany in a warm, friendly atmosphere.

Tuscany Farm to Table Cooking Class

2 hours 30 minutesFree Cancellation

from $180

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Top Attractions in Tuscany

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What are people saying about Tuscany

Pastamania 1st Pasta Class in Florence with Museum

Patricia_K, Apr 2026

We are now ‘official’ pasta makers!

A fabulous experience with Alessandra’s guidance and reaching! We love how Alesandra broke down all the steps required for our pastamania experience! Everything that we made tasted delicious! We definitely will be adding the new step of coating our pasta with butter and sage. So delicious! We bought ourselves an apron and a ravioli press so that we can continue of pasta making adventures back home with our family. We both thoroughly enjoyed this class and meeting everyone from different parts of the world. Thank you to Alesandra and everyone that we met for a wonderful dinner with some new friends.

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 .

Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

Brandon_T, Apr 2026

Two good wineries and a...

Two good wineries and a stop at a neat town to end it. Guide is good, small group oriented and a lot of fun. Does not seem like the wineries you are brought to are chosen because the guide is paid extra to bring groups in, they’re actually pretty good.

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

Miroslava_P, Mar 2026

Tuscan countryside

I loved the trip to Tuscan countryside with winetasting experience. Little villages had a charm. I loved countryside scenery watching from the minibus. So worth it. Our guide Antonio was very attentive and friendly. And I am grateful to our driver for a safe journey. Thank you both. PS. I felt like Picorino icecream in Pienza was one of the best icecreams I tried in Tuscan region. It had a strong yogurty taste and it was a bit salty. Unusual, but delicious. I had to treat myself to 2nd one.

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!!

Half day Chianti Vineyard Escape from Florence with Wine Tastings

Kathleen_C, Dec 2025

Fun day of wine tasting

The wine tour was very fun and informative! A nice bus ride through Tuscany and an experience of two different wineries. Both places were very accommodating and the wine & additional tasty treats were very good. We had a nice sunny cool day in December and the scenery was beautiful!

Half-Day Chianti Wine Tasting from Florence with Two Wineries

Lisa_B, Nov 2025

5 hour wine excursion shows you Tuscan countryside!

The bus trip TO the wineries is a valuable part of the trip! Put your phone away and gaze out the window, imagining the hundreds of years farmers harvested and artists captures the warm sunlight on the rolling hills. The wineries were charming and the tastings expertly hosted—and yet also very accessible to all wine drinkers. A great time; highly recommend!

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!