Top Tuscany Wine Tastings

Get a taste of aperitivo, Italy’s popular happy hour tradition, on a 2.5-hour tour in Florence. Begin the evening at a typical Florentine-style wine bar to indulge in Tuscan cheeses and salami while sipping some regional vino. Then, head out to explore some of Florence's most charming neighborhoods, before stopping off at a cocktail bar for a true Italian aperitif. Numbers are limited to 12 people to ensure an intimate experience.

Discover the many delights of Tuscany’s wine country on this small-group tasting tour from Florence. Travel along beautiful hillside roads through vineyards, olive groves and cypress trees. Visit 2 top-rated wineries in the famed Chianti Classico region, tour the cellars and learn how wine is produced using traditional methods. Taste different wines, along with olive oil and Tuscan specialties like fresh cheeses and bruschetta. Group size is limited to twenty-five participants for a more personalized experience.

Experience the famous beauty and flavor of Italy’s Chianti wine region on this half-day tour from Florence. Travel through the rolling hills and vineyards of the Tuscan countryside, stopping at two estate wineries to taste authentic Chianti wines and snack on regional specialties like bruschetta and cheese.

Experience the true flavor of the Tuscan countryside on this Chianti wine tour from Florence. Led by a professional tour escort, the tour includes visits local wineries set in scenic villages. Sample the most revered Tuscan wines, learn the characteristics of each blend and hear the winemakers’ secrets. Later, stop for a look at the fortress of Castellina before your return to Florence.

Art, history, countryside, food. Tuscany has it all. If you only have one day free, book this Tuscany day trip from Florence to discover the region’s highlights with a local guide. Explore the city of Siena and the cathedral, and then take to the Chianti hills for a Tuscan lunch and wine tasting. Roam the streets of San Gimignano, and travel to Pisa to admire the architectural drama of Cathedral Square — home to the UNESCO-listed Leaning Tower of Pisa. Upgrade to include skip-the-line entry, if you wish.

Spend a day in the beautiful Tuscan countryside sipping wine and making new friends. Visit authentic wineries for tours and generous tastings of world-famous varietals like Chianti Classico and Super Tuscan. Learn about the wines’ production and flavor profiles from a sommelier guide, and round out your palate with samplings of high-quality balsamic vinegar and olive and truffle oils. Also, visit the charming medieval village of San Gimignano for free time to explore the winding streets and artisan shops.

See all that Tuscany has to offer on this day trip to Pisa, Siena, and San Gimignano from Florence. Led by an expert guide, explore the main square and Gothic cathedral in Siena, followed by a traditional, 3-course lunch with wine. Afterward, enjoy free time to stroll the medieval streets of San Gimignano independently, as well as the city of Pisa, famous for its UNESCO-listed Leaning Tower. Your full day of sightseeing concludes with transportation back to Florence.

Get a true taste of Italy's famous Chianti region on this full-day wine and food tour departing from Florence. Led by a guide, travel through the Tuscan hills by a 4x4 off-road vehicle, stopping to visit a wine estate and historic villa, and a cellar specializing in bottles of Chianti Classico. Sample the finest specialties at each stop, and save room for a 3-course meal in the Chianti countryside before making the return trip to Florence.

Combine medieval gems, fine wines, and UNESCO-listed monuments on this full-day tour of central Tuscany from Florence. Marvel over the medieval castle of Monteriggioni; explore the architectural wonders of historic Siena; and admire the striking skyline of hilltop San Gimignano. Enjoy Siena and finish your tour with a wine tasting at a local winery in the Chianti region.

Escape the hustle and bustle of Florence on a day trip to the Chianti wine region, with round-trip transport from a convenient Florence location. In addition to navigating for you, your guide provides insight into the winemaking process at vineyards often missed by visitors to Tuscany. The day’s itinerary includes wine tastings, an authentic Tuscan lunch, and frame-worthy photo opportunities along the way.

Explore the Chianti area in the heart of Tuscany and taste some superb Chianti wines and Tuscan products. Visit 2 stunning wine estates, learn about the main technicians of wine production, admire the historical cellars and finally enjoy the wine tastings. You'll have the chance to visit two different Tuscan wineries, moreover, you'll join 2 wine tastings. In this way, you'll have the chance to learn more about the history and the culture of the wine. Immerse yourself in Chianti countryside and visit a medieval village, with narrow roads and typical shops.

Experience the UNESCO-listed Cinque Terre in one day with a guided tour through the five idyllic fishing villages of old-world Italy. Following the walking trails along the cliffs of the national park, you will see glorious views of this unspoiled stretch of the Italian Riviera. Check out the highlights and learn about the area as you complete a 3.4-mile (5.5-km) route with your guide. If you choose the tour option without hiking, the train will be used instead to move between villages.

See the Tuscan gems of San Gimignano, Siena, and Chianti on a day trip from Florence. Stop first in the city the medieval hilltop town of San Gimignano. Then it's off to the village of Chianti for a tasting of local blends and delicious lunch at a winery. Top off your trip in Siena to explore its historic city center with a stop at the Duomo.

Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this day trip from Siena. Led by an expert guide, travel to the cellars to learn about the production process and meet the locals behind the delicious red wine. Then, pause at a family-run winery for an authentic Tuscan lunch before exploring the village of Montalcino and the abbey of Sant'Antimo. Stop for additional tastings along the way and conclude with transportation back to Siena. Group size is reserved to eight people for a more intimate experience.

Take a break from Florence’s museums and escape to a trio of the most charming towns in Tuscany’s UNESCO-listed Val d’Orcia region. Taste prized red wine varietals like Nobile di Montepulciano and Brunello di Montalcino, stroll through medieval squares in Pienza, and sample authentic Tuscan fare on this all-inclusive tour that takes the planning and guesswork out of a day in wine country.

Discover the long winemaking conditions of Tuscany on this half-day tasting tour from Florence. Travel to a privately owned 12th-century winery in Chianti for a tour of the estate, vineyards, and family cellars. Learn about the region's distinctive and famous varietals from expert guides, and then savor the excellence for yourself with a guided tasting of estate wines, paired with a delicious Tuscan lunch.

Discover three of Tuscany’s most iconic destinations on a full-day tour from Florence by coach. Snap photos of the famous Leaning Tower and Piazza dei Miracoli in Pisa, stroll through the UNESCO-listed hill town of San Gimignano, and step inside Siena’s cathedral. Enjoy a traditional Tuscan lunch in Piazza del Campo.

Experience Siena and the Chianti region on this evening excursion, departing from Florence. Bypass the daytime crowds and arrive in Siena in the late afternoon to explore the Piazza del Campo. From there, visit a Tuscan wine cellar in the famous region of Chianti and enjoy a 4-course meal paired with local wines. After a romantic evening in the Tuscan countryside, return to central Florence.

Explore the Tuscan countryside in true Italian style — on a Vespa! After a short van ride from Florence and a riding lesson, spend a full day zipping along scenic country roads from the seat of your own personal Vespa. Pass by historic vineyards, villas and olive groves while your guide shares insight into local history and culture. Tour an organic farm and winery in the famed Chianti Rufina region, where you’ll enjoy a traditional Tuscan lunch and wine tastings.

Discover some of the highlights of Tuscany on this day trip from Florence by coach. Visit historical hill towns Pienza, Montalcino, and Montepulciano; admire the gorgeous, vineyard-covered scenery of Orcia Valley (Val d’Orcia); and enjoy cheese and wine tastings as you stop at local wineries and other venues. It’s a great day out in the Italian countryside.

Enjoy a full-day tour into the heart of the beautiful Tuscan countryside. Visit the town of San Gimignano, the wine territory of Chianti, the medieval town of Siena, and the Monteriggioni fortress. If you choose the option with lunch, you'll have the chance to spend your lunchtime in Piazza del Campo, where every year the Palio Horse Race takes place.

Explore the Italian Riviera on this day trip to the beautiful Cinque Terre from Florence, with transport between each small town provided. Led by a tour guide, discover each fishing village by coach, train, and boat, from the beaches of Monterosso to the charming streets of Riomaggiore. Stop for a swim in the turquoise waters and upgrade to include a traditional Italian lunch. Soak up all the character of this UNESCO-listed region before heading back to Florence.

Lose yourself in the luscious scenery and flavors of Italy’s most famous wine region on this half-day sunset tour of Chianti. Travel from Florence through the rolling hills and vineyards of the Tuscan countryside, stopping at the charming medieval village of Greve-in-Chianti and a local vineyard for a cellar tour and tasting of Chianti Classico and Super Tuscan wines. Sip the wines and enjoy a typical Tuscan snack as the landscape is washed in the golden hues of sunset.

Visit a 900-year-old Tuscan castle, where you can learn how to make pasta and taste wine from the historic cellars, on this half-day tour. With a small group, eat a lunch of pasta you made by hand and taste three wines. After lunch, enjoy free time to explore the vineyards and wander the castle's grounds.

Sip some of Italy's most famous wine during a 1.5-hour visit to an organic winery in the heart of the Chianti region. Tour the vineyards and organic winery between Radda and Panzano, right in the Chianti Classico wine-producing area. Learn about how local wines are made. Take part in a wine-tasting session at the conclusion of your tour, sampling between 3-6 wines with appetizers such as bread with olive oil produced on-site.