The 5 Best Day Trips and Wine Tours from Florence

Wine Tours from Florence: Discover Tuscany Beyond the City

Florence is not only a city of art and culture, it’s also the perfect starting point for exploring the Tuscan countryside and its wine regions. Just beyond the city, rolling hills, vineyards and historic estates offer a very different rhythm, shaped by wine, food and long standing traditions.

Our selection of wine tours from Florence is designed to offer more than simple tastings. Each experience is a chance to step into authentic wine growing areas, meet the people behind the bottles, and enjoy Tuscany at a human pace, whether you’re a first-time visitor or a returning wine lover.

Looking for more than a classic wine tour from Florence?

Many travelers are not just looking to taste wine, but to enjoy a complete day in the Tuscan countryside something relaxed, meaningful and easy to enjoy.

Some prefer a slower, more immersive experience, while others enjoy comparing different wineries and styles in one day. Choosing the right wine tour depends on how you like to travel, not just on how many stops you make.

Below you’ll find our curated selection of wine tours and day trips from Florence, designed around different travel styles and interests, not just itineraries.

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1. Exploring the Chianti Region: A Year-Round Wine Lover’s Paradise

Located just outside Florence, the Chianti region is one of Tuscany’s most iconic wine areas, known for its rolling hills, historic vineyards and family-run wineries. It’s a destination that appeals to both curious beginners and experienced wine lovers, offering beauty, culture and great wines throughout the year.

From the fresh greens of spring to the warm colors of the autumn harvest, every season adds a different atmosphere to the Chianti countryside, making it an ideal destination at any time.

Chianti wine tours offer a deeper understanding of Tuscany’s wine heritage, combining tastings with insights into local traditions, winemaking practices and the diversity of Chianti wines — all within a short drive from Florence.

Short on Time? The Perfect 2-Winery Wine Tour from Florence

Perfect for a relaxed, slow-paced day focused on wine, food and people.

Not everyone has the time, or the desire, for a full day wine tour with multiple stops.
If you’re looking for a more relaxed, focused and elegant wine experience, our 2 winery wine tour from Florence is often the perfect choice.

This experience is ideal for travelers who want to enjoy outstanding Tuscan wines without feeling rushed, while still escaping the city and immersing themselves in the countryside. You’ll visit two carefully selected, family run wineries, meet the producers, walk through the vineyards and cellars, and enjoy guided tastings that highlight the character of each estate and its wines.

Compared to longer itineraries, the 2 winery tour offers a slower pace and more personal interaction, making it especially popular with couples, first-time visitors to Tuscany, and travelers with limited time. It’s also a great option if you’re planning other activities in Florence on the same day but still want an authentic wine experience.

Despite being shorter, this tour never compromises on quality. We focus on organic and boutique wineries, avoiding large commercial stops, and ensuring that every tasting feels meaningful rather than repetitive. In just a few hours, you’ll gain a genuine understanding of Tuscan wine culture without turning your day into a marathon.

If you’re ready to go deeper and explore more wineries and wine styles in one day, our 3 winery wine tours from Florence are a natural next step.

Classic Chianti Wine Tour: Three Wineries

Ideal if you want a complete introduction to Chianti and enjoy comparing different wines

This tour is ideal for those seeking an introduction to Chianti’s rich wine culture. With visits to three esteemed wineries, you’ll be guided by local experts who offer a wealth of knowledge on Chianti’s winemaking techniques, terroir, and the distinctive characteristics of each varietal. Between tastings of Chianti’s famous reds and, in warmer months, refreshing whites and rosés, visitors can explore vineyard grounds, capture breathtaking photos of the landscape, and take in the historic atmosphere of each estate.

Extended Chianti wine Tour: Four Chianti Wineries with Lunch

For true wine lovers with a full day to dedicate to Chianti

For a more immersive experience, this tour extends to four wineries, each offering a unique take on Chianti winemaking. Begin with a tour of the vineyards and learn about Chianti’s signature grape, Sangiovese, which brings bright acidity and flavors of red fruits and earth to many of the region’s wines. The tour includes a farm-to-table lunch at one of the wineries, featuring traditional Tuscan dishes like pasta, cured meats, and cheeses that perfectly complement the wines. This experience offers an in-depth look at wine aging and tasting, guided by sommeliers who bring the art of wine to life.

Special Wine tour and Culture Tour: Exclusive tuscan Wineries and Local Heritage

For those seeking a blend of luxury and tradition, this curated tour takes you to three exclusive wineries, each celebrated for its unique winemaking techniques. You’ll enjoy a gourmet Tuscan lunch prepared by a renowned chef at the second winery, accompanied by wine pairings crafted to enhance each flavor profile. This experience often includes visits to local historical sites such as ancient castles or monasteries, providing a taste of Tuscany’s rich cultural heritage along with its wines.

Special Extras: Olive Oil Tasting

Many Chianti tours also feature tastings of cold-pressed Tuscan olive oil, a regional specialty that showcases the richness of Tuscany’s land. Sampling this fresh olive oil is a perfect complement to the wine tastings, offering visitors a well-rounded taste of Chianti’s agricultural treasures.

Whether you’re a wine novice or a connoisseur, the Chianti region offers an unforgettable journey through the flavors, history, and scenic landscapes of Tuscany.

2. Indulge in Flavors: Truffle, Wine, and Cheese Tour

Tuscany’s rich culinary heritage comes to life on the Truffle, Wine, and Cheese Tour, a must-do experience for food and wine lovers alike. This unique journey takes you deep into the region’s gastronomic traditions, blending the earthy elegance of truffles, the bold flavors of Tuscan wines, and the creamy richness of local cheeses. Whether you’re a seasoned foodie or just beginning to explore the art of pairing flavors, this tour offers something for everyone.

Highlights of the Truffle, Wine, and Cheese Tour

Guided Wine Tastings and Pairings

Begin your adventure at one of Tuscany’s renowned wineries, where you’ll enjoy a guided tasting of their finest wines. From full-bodied reds to delicate whites, each glass is thoughtfully paired with local cheeses. As you sip and savor, expert sommeliers provide fascinating insights into Tuscany’s unique terroir, grape varietals, and winemaking traditions.

A Truffle-Infused Culinary Delight

A highlight of this tour is the truffle-inspired lunch, featuring handmade pasta and local dishes. This meal is an opportunity to savor the earthy, aromatic qualities of Tuscany’s black truffles, paired perfectly with the region’s wines for a harmonious balance of flavors.

Explore Tuscan Craftsmanship

As the tour continues, visit charming wineries and historic cellars, where you’ll not only taste exceptional wines but also enjoy artisan delicacies.

This tour is more than just a tasting experience—it’s an exploration of Tuscany’s cultural roots. For centuries, truffle hunting, winemaking, and cheesemaking have been central to the region’s identity. Through stories and interactions with local experts, you’ll gain a deeper appreciation for the dedication and artistry behind these traditions.

Fun Fact: Tuscany’s Truffle Scene

Tuscany is one of Italy’s most prolific truffle-producing regions, with its forests yielding both prized black truffles and rare white truffles. Truffle hunting has been practiced here for centuries, often involving specially trained dogs or pigs to uncover these hidden culinary treasures.

This tour is perfect for anyone who wants to indulge in Tuscany’s most iconic flavors while learning about the history and craftsmanship that go into each bite and sip. From the thrill of truffle-infused dishes to the joy of savoring wine and cheese pairings, every moment offers a chance to celebrate the region’s culinary excellence.

Whether you’re a curious traveler or a dedicated epicurean, the Truffle, Wine, and Cheese Tour promises a delightful and enriching journey through Tuscany’s flavors. Raise your glass and toast to a day of unforgettable experiences!

3. Brunello di Montalcino: A Celebration of Tuscany’s Red Wine Majesty

Known for its world-class wines and stunning landscapes, Montalcino offers wine lovers an extraordinary opportunity to explore the essence of Tuscany. The Brunello di Montalcino Wine Tour is an unforgettable journey into the heart of this historic hilltop town, where exceptional winemaking and rich traditions blend seamlessly.

A Year-Round Destination for Wine Enthusiasts

Montalcino is celebrated year-round for its timeless charm and breathtaking views. In spring, the vineyards come alive with fresh greenery, while summer bathes the hills in golden light. Autumn transforms the landscape with warm harvest tones, and winter offers a quieter, cozier atmosphere for cellar tastings and intimate vineyard tours. No matter the season, the Brunello di Montalcino experience is a must for anyone passionate about great wine.

This tour combines education, tastings, and cultural immersion, making it perfect for both wine aficionados and those new to Tuscany’s winemaking traditions.

Highlights of the Brunello di Montalcino Tour

Discover Brunello’s Excellence

Begin your day with visits to two or three of Montalcino’s most esteemed wineries. Here, you’ll uncover the secrets of Brunello di Montalcino, a wine crafted exclusively from 100% Sangiovese grapes and aged for at least five years to develop its renowned complexity. Learn about the region’s unique terroir, the strict DOCG production regulations, and the meticulous art of barrel aging. Guided tastings will allow you to savor the rich layers of flavor—ripe dark fruits, earthy notes, and subtle spices—that define each vintage.

Explore Montalcino’s Historic Charm

In addition to its wines, Montalcino captivates visitors with its medieval allure. Stroll through the town’s cobblestone streets, visit artisan shops, and soak in the panoramic views of vineyards and olive groves from its iconic fortress. Montalcino’s timeless beauty is a reflection of its deep-rooted traditions, making it a destination that perfectly complements the Brunello experience.

A Gourmet Culinary Experience

No visit to Montalcino is complete without indulging in Tuscany’s signature flavors. Brunello’s bold and structured profile pairs wonderfully with rich regional dishes. Many tours include a gourmet lunch at a local winery or trattoria, where you’ll enjoy a selection of Tuscan specialties made with fresh, seasonal ingredients. Each dish is thoughtfully paired with Brunello wines, creating a symphony of flavors that elevate the tasting experience.

Tuscany’s Red Wine Majesty

Brunello di Montalcino stands as one of Italy’s most prestigious wines, a masterpiece of craftsmanship and tradition. Its aging process, lasting years in oak barrels and bottles, produces a wine that is both powerful and elegant—a true reflection of the region’s dedication to excellence.

Why Choose a Brunello Tour from Florence?

Starting your journey in Florence, this tour offers a seamless blend of wine education, cultural exploration, and scenic beauty. Whether you’re marveling at the vineyards, savoring expertly paired food and wine, or exploring Montalcino’s rich history, every moment is designed to delight the senses and deepen your appreciation for Tuscany’s winemaking heritage.

Raise your glass to Brunello di Montalcino and experience the best of Tuscany on this unforgettable adventure!

4. A Day in Medieval San Gimignano: White Wine and Timeless Charm

Step back in time with a visit to San Gimignano, a hilltop town steeped in history and famed for its stunning medieval towers and exceptional wines. A San Gimignano wine tour offers the perfect blend of cultural exploration and wine discovery, making it a must for anyone seeking to experience Tuscany’s unique treasures.

San Gimignano, a UNESCO World Heritage Site, welcomes visitors throughout the year, with each season adding its own special touch to the experience. In spring, the town is surrounded by blooming fields and lush greenery, while summer offers vibrant energy as sunlight bathes the medieval architecture. Autumn’s warm hues and the grape harvest season enhance the allure of the vineyards, while winter brings a quieter, romantic atmosphere to the cobblestone streets and intimate wine cellars.

Whether you’re a seasoned wine enthusiast or simply eager to explore Tuscany’s cultural heritage, a day in San Gimignano is sure to captivate your senses.

Highlights of the San Gimignano Wine Tour

Discover the Historic Town

Begin your journey with a leisurely stroll through San Gimignano’s charming streets, lined with medieval towers, historic buildings, and artisan shops. Known as the “Town of Fine Towers,” San Gimignano boasts 13 surviving towers that once symbolized the wealth and influence of its noble families. Visit landmarks like Piazza della Cisterna, the town’s main square, or Piazza del Duomo, home to the beautiful Collegiate Church of San Gimignano. From every corner, enjoy breathtaking views of the Tuscan countryside stretching into the horizon.

Taste the Unique Vernaccia di San Gimignano

San Gimignano is home to Vernaccia di San Gimignano, a white wine celebrated for its crisp, floral, and slightly mineral notes. Produced exclusively in this region, Vernaccia is one of Tuscany’s most prized wines and the first white wine in Italy to receive DOCG status. Visit two or three local wineries where you’ll meet passionate winemakers and learn about Vernaccia’s history, production process, and unique terroir. Guided tastings allow you to savor the wine’s refreshing character while enjoying the stories behind each bottle.

A Delightful Tuscan Lunch

No trip to Tuscany is complete without indulging in its culinary delights. Many San Gimignano wine tours include a gourmet lunch at a local winery or trattoria. Here, you’ll enjoy traditional dishes crafted with fresh, seasonal ingredients, perfectly paired with Vernaccia wines. From handmade pastas to locally sourced vegetables and cheeses, each bite complements the wine, creating a memorable dining experience.

Panoramic Views and Photo Opportunities

Beyond its wine and history, San Gimignano offers some of the most picturesque views in Tuscany. Take time to enjoy panoramic vistas of the surrounding vineyards, olive groves, and rolling hills. Whether you’re capturing photos of the medieval skyline or the peaceful countryside, the beauty of San Gimignano will leave a lasting impression.

Why Choose a San Gimignano Wine Tour from Florence?

Starting your journey in Florence, this tour is the perfect escape from the bustling city, allowing you to immerse yourself in the tranquil charm of the Tuscan countryside. With its combination of history, wine, and scenic beauty, San Gimignano offers an experience that appeals to both cultural explorers and wine lovers.

This tour also provides an excellent opportunity to learn about Vernaccia’s unique qualities, including how it pairs beautifully with Tuscan cheeses and dishes. A wine and food pairing session is highly recommended to fully appreciate the harmonious flavors of the region.

Vernaccia di San Gimignano: A Wine with History

Vernaccia di San Gimignano is more than just a wine—it’s a symbol of Tuscany’s winemaking heritage. Its origins date back to the 13th century, and it has been praised by poets and nobility for centuries. Its crisp, refreshing profile, with notes of citrus, almond, and minerality, makes it a versatile wine that pairs well with everything from seafood to Tuscan pecorino cheese.

A Day to Remember

A San Gimignano wine tour is more than just a tasting—it’s a journey into the heart of Tuscany’s history, culture, and natural beauty. From the medieval charm of the town’s towers to the crisp elegance of Vernaccia wines, every moment is designed to delight your senses.

Whether you’re exploring ancient streets, savoring Tuscan dishes, or raising a glass of Vernaccia to the stunning countryside views, your day in San Gimignano promises to be unforgettable.

Raise your glass and toast to the timeless beauty of San Gimignano and its exceptional wines!

5. Nobile di Montepulciano Wine Tour: A Journey into Tuscany’s Wine Heritage

Embark on an unforgettable journey from Florence to Montepulciano, a medieval hilltop town renowned for its exceptional Vino Nobile di Montepulciano. This full-day tour invites wine lovers to explore Tuscany’s rich viticultural heritage, indulge in traditional flavors, and soak in the breathtaking landscapes that define this iconic region.

Discover Montepulciano: A Wine Lover’s Paradise

Montepulciano, located in southern Tuscany, is celebrated for its rolling vineyards, historic charm, and one of Italy’s most prestigious wines—Vino Nobile di Montepulciano. This DOCG wine, crafted primarily from Prugnolo Gentile (a Sangiovese clone), is known for its balance, elegance, and depth. Unlike Montepulciano d’Abruzzo, which hails from central Italy, Vino Nobile is produced exclusively in the Montepulciano region and reflects centuries of winemaking tradition.

Whether you’re a seasoned oenophile or a wine-tasting novice, this tour is tailored to provide a comprehensive introduction to Montepulciano’s wine culture.

Tour Highlights

Winery Visits and Tastings

Your day begins with visits to some of the most esteemed wineries in Montepulciano. Guided by passionate winemakers, you’ll learn about the unique terroir, traditional production methods, and meticulous aging process that make Vino Nobile so extraordinary. Tastings typically include a selection of Vino Nobile di Montepulciano, its younger sibling Rosso di Montepulciano, and Riserva vintages for a deeper appreciation of the wine’s complexity and aging potential.

Explore the Vineyards and Cellars

As you tour the vineyards, you’ll discover how Montepulciano’s location—perched on a tufa hill and surrounded by rolling hills—contributes to the wine’s character. Delve into the cool, stone-lined aging cellars where barrels of wine rest, developing the rich flavors that make Vino Nobile a masterpiece.

Traditional Tuscan Lunch

No Tuscan wine tour is complete without savoring the region’s cuisine. Many tours include a gourmet lunch at a local winery or trattoria, where you’ll enjoy traditional dishes crafted from fresh, seasonal ingredients. Paired with the wines of Montepulciano, this culinary experience highlights the harmonious relationship between Tuscan food and wine.

Medieval Charm of Montepulciano

In addition to wine, Montepulciano offers a feast for the eyes. You’ll have time to wander the cobblestone streets of this historic town, visiting landmarks such as Piazza Grande, the Cathedral of Santa Maria Assunta, and the 16th-century Palazzo Comunale. The panoramic views of the Val d’Orcia and Val di Chiana from Montepulciano are nothing short of spectacular.

Why Choose a Nobile Wine Tour from Florence?

This tour is perfect for anyone seeking to explore Tuscany beyond Florence’s cityscape. It provides a seamless blend of wine education, cultural immersion, and scenic beauty, making it an ideal day trip. The convenience of starting and ending your journey in Florence ensures a stress-free experience, allowing you to focus on enjoying the wine, food, and scenery.

Book Your Nobile Wine Tour

Whether you’re a wine enthusiast or simply looking to immerse yourself in the beauty of Tuscany, a Nobile di Montepulciano wine tour from Florence is a must. With guided tastings, traditional food, and the timeless charm of Montepulciano, this tour promises to leave you with a deeper appreciation for Tuscany’s winemaking traditions and its exceptional Vino Nobile.

Raise your glass and toast to a day of discovery, flavor, and unforgettable memories in the heart of Tuscany!

Your Perfect Tuscan Escape

From the rolling hills of Chianti to the medieval towers of San Gimignano, and from the rich reds of Brunello to the elegant Vernaccia and Vino Nobile, Tuscany offers an unparalleled array of wine and cultural experiences. These top five wine tours from Florence are carefully curated to showcase the region’s iconic flavors, breathtaking scenery, and centuries-old traditions, ensuring every moment is as enriching as it is delightful.

Many guests choose Florence as their base while exploring Tuscany’s wine regions. For those looking for a refined and central stay, we also offer a private designer loft in the heart of the city — an ideal place to relax after a day of tastings and countryside discoveries.
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Whether you’re savoring a bold Brunello with a gourmet lunch, discovering the art of truffle hunting, or wandering through the cobblestone streets of Montepulciano, each tour invites you to immerse yourself in the heart of Tuscany’s wine heritage. The journey doesn’t just end with the wine—it’s complemented by authentic Tuscan cuisine, artisan craftsmanship, and the kind of views that stay etched in your memory.

With Florence as your gateway, these wine tours are perfect for beginners exploring their first vintages and seasoned enthusiasts looking for their next favorite bottle. Each season adds its own charm to the Tuscan countryside, making every trip uniquely magical.

So, raise your glass, toast to the flavors of Tuscany, and let these unforgettable wine tours become the highlight of your Italian adventure! Whether you choose to dive into the history of Chianti, the culinary treasures of San Gimignano, or the prestige of Brunello and Vino Nobile, you’re guaranteed a day filled with discovery, indulgence, and inspiration. Cheers to Tuscany!

Not sure which wine tour fits your travel style?
Our team is happy to help you choose the experience that feels right for you.