Tuscany Wine Tour Itinerary

Exploring Tuscany: The Ultimate Wine Tour Itinerary for Wine Lovers

Tuscany, with its rolling hills, picturesque vineyards, and world-renowned wines, is a dream destination for wine lovers. This region of Italy offers a perfect blend of stunning landscapes, historic towns, and culinary delights. If you’re planning a trip to Tuscany, this ultimate wine tour itinerary will guide you through the best wine regions, must-visit wineries, and unforgettable experiences.


Imagine sipping a glass of full-bodied Chianti while overlooking the sun-drenched vineyards of Tuscany. The region’s diverse wine offerings, combined with its rich cultural heritage and breathtaking scenery, make it a paradise for wine enthusiasts. This itinerary is designed to provide you with a comprehensive and immersive wine experience, from exploring charming villages to tasting some of the finest wines in the world.

What is a Wine Tour?

Day 1: Arrival in Florence

Morning: Arrival and Accommodation

Arrive in Florence, the capital of Tuscany and a city steeped in art and history. Settle into your accommodation, whether you choose a luxurious hotel or a cosy B&B.

Afternoon: Explore Florence’s Wine Bars

Start your Tuscan wine adventure by exploring Florence’s vibrant wine bar scene. Visit Enoteca Pitti Gola e Cantina, a renowned wine bar near the Pitti Palace, offering an extensive selection of Tuscan wines. Sample a few glasses to get an introduction to the region’s diverse wine styles.

Evening: Dinner with Wine Pairings

Enjoy dinner at a local restaurant that focuses on regional cuisine and wine pairings. Osteria del Cinghiale Bianco is an excellent choice, known for its traditional Tuscan dishes and curated wine list. Savor dishes like pappardelle with wild boar ragu, paired with a robust Chianti Classico.

Day 2: Chianti Classico Region

Morning: Castello di Verrazzano Winery

Drive to the heart of the Chianti Classico region. Your first stop is Castello di Verrazzano, a historic winery with stunning views and a rich heritage. Take a guided tour of the vineyards and cellars, followed by a wine-tasting session where you can sample their acclaimed Chianti Classico.

Afternoon: Antinori nel Chianti Classico

After lunch at a traditional Tuscan trattoria, visit Antinori nel Chianti Classico, an architectural masterpiece and modern winery. Explore the innovative structure and enjoy a guided tasting of their exceptional wines, including the famous Tignanello.

Evening: Stay at an Agriturismo

Check into a charming agriturismo (a farm stay) in the Chianti region. These rustic accommodations offer an authentic Tuscan experience, with opportunities to taste home-cooked meals and local wines.

Day 3: Montalcino and Brunello Wines

Morning: Biondi Santi Winery

Travel to Montalcino, home to the prestigious Brunello di Montalcino wine. Start your day at Biondi Santi Winery, the birthplace of Brunello. Tour the vineyards and cellars, and enjoy a tasting of their renowned wines.

Afternoon: Poggio Antico Winery

After a leisurely lunch in Montalcino, head to Poggio Antico Winery. This winery is known for its picturesque setting and high-quality Brunello. Take a vineyard tour and participate in a tasting session to experience the depth and complexity of Brunello wines.

Evening: Sunset at the Fortress of Montalcino

End your day with a visit to the Fortress of Montalcino. Enjoy panoramic views of the surrounding countryside as the sun sets, casting a golden glow over the vineyards.

The Best Luxury Wineries to Visit in the World
A Traditional Winery

Day 4: Montepulciano and Vino Nobile

Morning: Avignonesi Winery

Head to Montepulciano, famous for its Vino Nobile di Montepulciano. Begin your visit at Avignonesi Winery, where you can tour the vineyards and cellars. Sample their Vino Nobile and learn about the winery’s commitment to sustainable practices.

Afternoon: Cantina Contucci

After lunch in Montepulciano, visit Cantina Contucci, one of the oldest wineries in the region. Explore their historic cellars and enjoy a tasting of their esteemed Vino Nobile di Montepulciano.

Evening: Stroll Through Montepulciano

Spend the evening strolling through Montepulciano’s historic streets. Visit local shops, enjoy a gelato, and soak in the charming atmosphere of this medieval town.

Day 5: San Gimignano and Vernaccia

Morning: Azienda Agricola San Quirico

Travel to San Gimignano, known for its medieval towers and Vernaccia di San Gimignano wine. Start your day at Azienda Agricola San Quirico, where you can taste their crisp and refreshing Vernaccia.

Afternoon: Tenuta Torciano

After a delightful lunch with views of San Gimignano’s iconic towers, visit Tenuta Torciano. Participate in a cooking class to learn how to prepare traditional Tuscan dishes, followed by a wine pairing session with their excellent Vernaccia and other wines.

Evening: Explore San Gimignano

Spend the evening exploring San Gimignano’s historic centre. Wander through its narrow streets, visit local artisans, and enjoy the ambience of this enchanting town.

Day 6: Bolgheri and Super Tuscans

Morning: Ornellaia Winery

Drive to Bolgheri, home to the famous Super Tuscan wines. Begin your day at Ornellaia Winery, known for its exceptional wines and stunning estate. Take a guided tour and enjoy a tasting of their acclaimed Super Tuscans.

Afternoon: Tenuta San Guido (Sassicaia)

After lunch at a local enoteca, visit Tenuta San Guido, the birthplace of Sassicaia. Explore the vineyards and cellars, and savour a tasting of their legendary Super Tuscan wines.

Evening: Return to Accommodation

Return to your accommodation for a relaxing evening. Reflect on the day’s experiences and enjoy a quiet night in the Tuscan countryside.

Fine Wines
Fine Wine

Day 7: Return to Florence

Morning: Leisurely Breakfast and Departure

Enjoy a leisurely breakfast at your agriturismo. Take some time to relax and soak in the tranquil surroundings before departing.

Afternoon: Return to Florence

Drive back to Florence for some last-minute sightseeing or shopping. Visit the local markets, pick up some souvenirs, or simply enjoy a stroll through the city.

Evening: Farewell Dinner

End your Tuscan adventure with a farewell dinner at a renowned Florence restaurant. Il Palagio at the Four Seasons Hotel offers a sophisticated dining experience with an impressive wine list, making it the perfect place to toast your journey.

Travel Tips


Renting a car is the best way to explore Tuscany at your own pace. If you prefer not to drive, consider hiring a private driver or joining a guided wine tour.


Consider staying in boutique hotels or historic villas for a touch of luxury.

Wine Shipping

Many wineries offer shipping services so you can send your favourite wines home. Check with each winery for details on shipping options and costs.

Local Customs

When visiting wineries, it’s customary to make a reservation in advance. Tasting fees are common but often waived with a purchase. Be sure to enjoy the wine responsibly and take time to savour each sip.


Tuscany’s wine regions offer an unparalleled experience for wine lovers. From the rolling vineyards of Chianti Classico to the historic cellars of Montepulciano and the iconic Super Tuscans of Bolgheri, this ultimate wine tour itinerary provides a comprehensive guide to exploring the best of Tuscan wines. Whether you’re a seasoned oenophile or a casual wine enthusiast, Tuscany promises an unforgettable journey filled with exquisite wines, breathtaking landscapes, and warm hospitality.

Embark on your Tuscan wine adventure and discover the magic of this enchanting region. Share your experiences and favourite Tuscan wines in the comments below, and let’s celebrate the rich flavours of Tuscany together!

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