Best Wine Tours in Tuscany

Enjoy a saffron-based meal with a tasting of four organic and biodynamic wines and six extra virgin olive oils at a farm facing one of San Gimignano’s oldest vineyards — bruschetta and crostini, saffron pasta, cheeses, smoked beef or egg, and homemade cake.

Enjoy a guided tasting in front of one of San Gimignano’s oldest Vernaccia vineyards — four organic and biodynamic wines, including Vernaccia di San Gimignano and Chianti Colli Senesi, six extra virgin olive oils and balsamic vinegar, paired with homemade snacks and bruschette.

Visit a historic villa and its museum near Florence, tour the working winery and the traditional Vinsantaia, then taste four estate wines, including a white or rosé, two Chianti wines and the estate’s Vin Santo, with local cheeses and extra virgin olive oil.

Enjoy a four-course truffle lunch at a San Gimignano farm facing one of the town’s oldest vineyards — bruschetta and crostini with fresh truffle, organic pasta, smoked beef or eggs with truffle and a dessert — paired with four organic and biodynamic wines and six extra virgin olive oils.

Explore a historic estate archive, its aging cellars and the Vinsantaia where Vin Santo ages in traditional caratelli barrels, then taste five estate wines — three reserves, a Vin Santo and a signature Vermouth — with local cheeses and extra virgin olive oil.

Experience the timeless beauty of a historic castle at sunset — a guided evening tour of the grounds, historic gardens and wine collection, illuminated by golden Tuscan light, followed by a seasonal Tuscan dinner with traditional and contemporary dishes, expertly paired with Chianti Classico wines.

Join an exclusive vertical tasting of five historic vintages at a Chianti estate in Barberino Tavarnelle, guided by an expert winemaker or sommelier through how time, terroir and technique shaped each wine — choose between a Chianti Classico Riserva vertical or a Supertuscan vertical.

Tour a historic villa and its museum near Florence, explore the working winery and the traditional Vinsantaia where Vin Santo ages, then learn professional tasting technique and compare three wines in a private small-group tasting.

Taste eight wines among historic vineyards in Mercatale Val di Pesa, 30 minutes from Florence — start with a wine and olive oil class, visit the medieval wine cellars, walk the vineyards and olive groves, then label your own bottle to take home.

Spend 4.5 hours at a Tuscan estate in Mercatale Val di Pesa — a wine and olive oil class, a walk through vineyards and olive groves, a visit to medieval wine cellars, and a six-course Tuscan meal paired with a tasting of 10 selected wines.

Enjoy a Chianti Winery Lunch Experience in Radda in Chianti, Tuscany, featuring a traditional 4-course meal paired with local Chianti wines!

A rare, 2-hour guided tasting in San Gimignano where guests taste Tuscan wines directly from the oak barrels — discovering the future of celebrated vintages before they reach the bottle.

Vine, wine and dine in the birthplace of Chianti Classico — a guided tour of a historic 11th-century castle, its role in Italian political and winemaking history, a walk through the vineyards, a private tasting of top-tier Gran Cru wines, finishing with a gourmet three-course lunch at the estate’s own restaurant.

Discover a Chianti Classico wine & olive oil experience with blind tastings, sensory rooms, expert sommeliers, and the history of the Black Rooster

A 90-minute guided tour of a Tuscan winery estate near San Gimignano — walk the vineyards, visit the wine cellar and barrel room, then taste Tuscan wines, olive oils, and balsamic vinegar paired with local cheeses, salami, and bruschetta.

Enjoy a refined 30-minute guided tasting in Barberino Tavarnelle, in the Chianti hills — three distinguished wines, from an elegant Chianti Classico DOCG to a complex Riserva and a bold IGT red, each explained with expert commentary, paired with traditional Tuscan bread and the estate’s own extra virgin olive oil.

A 4-hour adventure through the Tuscan vineyards and olive groves by 4×4 Jeep, followed by a panoramic aperitif and a full Tuscan lunch with a guided wine school covering 10 wines, three olive oils, and balsamic vinegar.

Enjoy a full Chianti wine & olive oil tasting experience with guided sensory pathway, Chianti Classico wines, PDO olive oil, and local food pairings

Join an exclusive tasting at one of Italy’s most storied wine estates in Gaiole in Chianti — five premium wines from the Gran Selezione and Supertuscan collections, guided by knowledgeable staff through the estate’s commitment to sustainability, biodiversity and innovation.

An exclusive 2.5-hour journey into one of Tuscany’s most treasured wine traditions — visit a working vinsantaia near San Gimignano and taste four sweet and late harvest wines paired with traditional Tuscan dessert bites.

A 3-hour guided tour of two Tuscan wineries near San Gimignano — explore vineyards and cellars at the first estate, then transfer by shuttle to a second winery for a tasting with panoramic views of the medieval towers.

Explore Chianti Classico vineyards on a guided trek with a premium wine tasting, cellar visit, and Riserva and Gran Selezione wines in Tuscany

A focused 60-minute guided tasting in San Gimignano dedicated entirely to Tuscan white and sparkling wines — from Vernaccia di San Gimignano DOCG to Prosecco, Vermentino, and Chardonnay — paired with Tuscan cheeses, salami, and bruschetta.

Take a break in a garden or private tasting room overlooking San Gimignano’s medieval towers — taste four organic and biodynamic wines, six extra virgin olive oils from the farm’s own production and a selection of organic Pecorino Toscano cheeses, with homemade Km 0 bruschetta.

Craft your own custom wine blend in an exclusive private masterclass, working with up to four grape varieties drawn directly from oak barrels — learn expert tasting techniques, experiment with combinations, finish with a Tuscan light lunch and take home three personalized bottles with your own label.

Step into a castle’s private medieval halls, once the backdrop of the Pazzi Conspiracy, rarely open to the public — then explore the historic aging cellars before a professionally led tasting of four premium estate wines, paired with artisanal biodynamic products and an introduction to tasting technique.

A guided 60-minute tasting in San Gimignano, pairing 12 Tuscan wines — from Brunello di Montalcino to three Super Tuscans — with a curated selection of Italian artisan cheeses, olive oils, and balsamic vinegar.

A 60-minute wine school experience in San Gimignano, tasting a curated selection of Tuscan red and white wines, three olive oils, and balsamic vinegar, paired with local cheeses, salami, and bruschetta.

A 3-hour off-road adventure through the olive groves near San Gimignano, followed by a guided tasting of 10 extra virgin olive oils — from Chianti Classico DOP to truffle and lemon infusions — paired with Tuscan cheeses, salami, and bruschetta.

Step into a 200-year-old Tuscan winery and discover where Tuscany was born. Enjoy a guided historic tour followed by a premium wine and food pairing using seasonal farm products and local specialties.

Spend a morning at an 11th-century castle in the heart of Chianti Classico, the historic seat of a family of winemaking pioneers — tour the state-of-the-art winemaking facilities and aging cellars, finishing with a guided tasting in an elegant private tasting room.

Enjoy a curated 30-minute tasting of signature Chianti wines, guided by a knowledgeable member of the team — complemented by the estate’s own extra virgin olive oil, paired with artisan Tuscan bread, local salame and regional cheeses. This tasting does not include a winery tour.

Join an immersive tour at a Chianti winery, gaining firsthand insight into proud winemaking traditions from vineyard to bottle — a tasting of three signature wines paired with the estate’s own extra virgin olive oil, Tuscan bread, local salame and artisan cheese.

Walk the vineyards, olive groves and wine cellar of a Chianti Classico estate in Barberino Tavarnelle — learn the full winemaking process, taste three estate wines paired with a light Tuscan lunch of bruschetta, pasta and a platter of Pecorino, prosciutto and salami, finishing with Vin Santo and cantucci.

An exclusive 90-minute private guided tour of a Tuscan winery estate near San Gimignano — walk the vineyards, visit the cellar, and enjoy a private tasting of Tuscan wines, olive oils, and balsamic vinegar, just for your group.

Walk the vineyards, olive groves and wine cellar of a Chianti Classico estate in Barberino Tavarnelle — learn the full winemaking process from grape to bottle, taste three estate wines paired with local cheeses, cured meats and Tuscan bread with olive oil, finishing with Vin Santo and cantucci.

Step into the medieval wine cellars of a historic castle in Pontassieve — a guided journey through centuries of winemaking tradition, with storytelling about the castle’s heritage and an itinerant tasting of three estate wines, including biodynamic options and snacks produced on the property.

Immerse yourself in an exclusive wine tasting at a historic castle in the heart of Chianti Classico — three premium wines in an elegantly restored historic room, followed by a self-guided visit through the estate’s scenic gardens and grounds at your own pace.

Learn about wine, olive oil and balsamic vinegar at a Tuscan estate in Mercatale Val di Pesa, tour a cellar dating back to the 1620s and the vineyards with a white wine aperitif, then enjoy a light Tuscan lunch of cheeses, cured meats and nine selected wines.

Cook a complete Tuscan meal with local chefs in a charming traditional estate kitchen near Florence — fresh handmade pasta, a seasonal main course and a classic dessert — then share it on the estate’s scenic terrace with estate wines, water and coffee.

Hike around 14 km through the forests, vineyards, olive groves and historic landmarks of an estate near Florence with environmental guides, learning about its geology, flora, fauna and heritage, with possible stops to meet local cheesemakers, beekeepers and iris growers.

Tour the castle’s medieval wine cellars with an itinerant tasting of three estate wines, then join a comprehensive hands-on cooking class — fresh handmade pasta, chicken thighs braised in Vin Santo, olive paté and traditional Schiacciata alla Fiorentina — finishing with a shared meal paired with the estate’s wines.

Enjoy a Tuscan Picnic Experience with local food, regional wines and scenic countryside views in the heart of Tuscany. A relaxing and authentic escape!