Chianti is located just a short drive away from Florence, making it an easy and accessible day trip for visitors. More than dozens of tour companies offer guided tours of the region. Here are some of our favorite ones.

Best Half-Day Wine Tours from Florence

This is one of our top half-day tours in Florence (and it’s not just us who love it! Check out the reviews from other visitors who have booked the experience!).

Chianti Half-Day Wine Tour from Florence

• Duration: 5 hours 30 minutes (approx.)
• Price: From $55
• Operated by: myTour in Italy
• Why It’s Great: This tour is perfect for those who want a quick getaway from Florence but don’t have a full day to spare. You’ll visit two boutique wineries (Agricola Poggio Ai Laghi and Castellina In Chianti) and taste amazing wines. Your tour will end at the medieval town Monteriggioni. The tour includes transportation in an air-conditioned coach, so you don’t have to worry about drinking and driving. We loved how laid-back this tour was—perfect if you just want to sip wine and soak in the views without any rush.
• Pro Tip: Try out the local red and white wines, and also taste some balsamic vinegar and extra-virgin olive oil while taking in the beautiful views of the Chianti countryside.

Best Full-Day Wine Tours from Florence

When looking for full-day tours, we highly recommend considering reputable wine tour agencies. Be sure to check the next ones out!

Tuscany Day Trip: Siena, San Gimignano, Pisa, and Lunch at a Winery

• Duration: 11-12 hours (approx.)
• Price: From $119
• Operated by: Walkabout Florence Tours
• Why It’s Great: You get a full-day experience exploring some of Tuscany’s most famous towns, plus an amazing lunch and wine tasting at an organic winery, Fattoria Poggio Alloro. I did this tour on my first visit to Tuscany, and it was an incredible way to see the region’s highlights. The lunch at the winery was the cherry on top—fresh organic farm food of homemade pasta, cured meats (homemade prosciutto and salami), local cheeses, a home garden salad, and Tuscan biscotti.
• Pro Tip: Wear comfortable shoes! You’ll be doing a fair bit of walking in Siena, San Gimignano and and Pisa.

Full-Day Tuscany Castles Tour with Wine Tasting

• Duration: 7 hours (approx.)
• Price: From $318
• Operated by: Italy and Tour Sas
• Why It’s Great: This tour feels like you’re stepping back in time. You’ll visit two wineries, Castello del Trebbio and Tenuta di Bossi in the Chianti region, tour their cellars, and enjoy tastings of their exclusive wines. The tour includes a 2-course lunch at a traditional Tuscan restaurant. The castles are not just beautiful—they’re steeped in history, and the guides are fantastic at weaving in stories about the region’s past.
• Pro Tip: Tenuta Bossi is an impressive Renaissance villa with origins dating back to the 15th century. It is proudly owned by the prestigious Gondi family of Florence. Don’t miss the opportunity to taste their renowned Vinsanto “Cardinal de Retz.”

Siena, San Gimignano & Chianti Private Tour

• Duration: 8 hours (approx.)
• Price: From $850 (for up to 7 people)
• Operated by: Bespoke Italian Tours
• Why It’s Great: If you want something a little more intimate, this private tour is a wonderful option. You’ll have your own driver who will tailor the day to your preferences. Visit Siena’s famous Piazza del Campo, enjoy a wine-tasting lunch at a Castellina In Chianti winery, and finish off the day with a gelato in San Gimignano. We took this tour with a small group of friends, and it was hands down one of the best days we had in Tuscany. There’s nothing like having your own schedule and private guide!
• Pro Tip: If you’re traveling with a group, this tour is great value, especially for the personalized experience.

Best Multi-Day Wine Tours

We have picked a fantastic multi-day wine tour that provides an excellent opportunity to thoroughly explore the area and is especially perfect for those who love Brunello and Chianti wines.

2-Days of Tuscany discovering the Nobile, Brunello, Chianti area

• Duration: 2-days
• Price: From $1,042
• Operated by: Tuscansafari Srl
• Why It’s Great: This two-day tour takes you through the scenic landscapes of Montalcino, Montepulciano, San Gimignano, and Siena, with stops at renowned local wineries to taste iconic wines such as Brunello di Montalcino, Chianti Classico, and Vino Nobile.
  • Day One: Montalcino, Val d’Orcia, and Montepulciano: Your adventure begins in the picturesque Val d’Orcia, a UNESCO World Heritage site. The next stop is Montalcino, the heart of Brunello production. Here, you’ll visit Piombaia Winery, where you’ll taste Brunello di Montalcino, Rosso di Montalcino, and the rare Rosso of Sant’Antimo. Next, you’ll head to Montepulciano, famous for its Vino Nobile wines. A visit to the historic Contucci Cellars offers the chance to taste Vino Nobile di Montepulciano, along with Rosso di Montepulciano.
  • Day Two: Siena, San Gimignano, and Chianti: On the second day, you’ll head to Siena, a city steeped in history, before venturing to San Gimignano, where you’ll sample the crisp and refreshing Vernaccia, a white wine that’s unique to the area. Afterwards, you’ll head to Chianti. At Casa Emma, you’ll taste Chianti Classico and Supertuscan wines. Here, you’ll also have the opportunity to try locally-produced olive oil and balsamic vinegar, while learning about the Sangiovese grape’s significance in Tuscan winemaking. The day ends in Castellina in Chianti, a historic town known for its medieval streets and ancient architecture, like the charming Via delle Volte and the imposing fortress.
• Pro Tip: Don’t miss a stop at the world-renowned Gelateria Dondoli in San Gimignano, where you can treat yourself to the “World Champion” gelato.

Best Tours for First-Time Visitors

If you’re a first-time visitor to Chianti, we’ve got a great wine tour recommendation for you. It’s an awesome adventure with really cool transportation, and you can book it as a private tour too!

Chianti Safari: Tuscan Villas with vineyards, Cheese, Wine & Lunch from Florence

 

• Duration: 9 hours (approx.)
• Price: From $255
• Operated by: Walkabout Florence Tours
• Why It’s Great: If you’re new to Tuscany and Chianti wines, this is a great introductory tour. You’ll spend a full day exploring the Chianti countryside, cruising around in a 4×4 minibus, all while enjoying local food. Your adventure kicks off with a visit to a prestigious Villa le Corti winery, owned by one of Italy’s most renowned families. You’ll get to sample a range of wines paired with local cured meats and olive oils. Next, it’s time to refuel with a hearty Tuscan 3-course meal featuring regional favorites like freshly made pasta and, of course, a glass (or two) of Chianti wine. You’ll hop back on the minibus and head deeper into the Tuscan countryside. Your final stop is another gorgeous Poggio Torselli winery and sample the renowned Chianti Classico wine. After wandering around and learning more about the region’s rich wine history, you’ll finish off the day with a tasting of three exceptional wines, paired with local cheeses. PS. Check our article that covers the dos and don’ts of pairing Italian cheese and wine for a better understanding.
• Pro Tip: Don’t forget to explore the beautiful gardens of Villa le Corti. Be sure to wear comfortable shoes, especially if you plan to explore the vineyards and estates. And remember to bring your camera – you’ll want to capture the amazing scenery! P.S. If you prefer a private tour, a Private Chianti Safari tour is also available.

Best Tours for Wine Enthusiasts

If you’re really into wine, you’ll love this private wine tour. It’s a full-day experience where you can taste some truly amazing wines.

Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour

• Duration: 9 hours (approx.)
• Price: From $521
• Operated by: Prestige Rent
• Why It’s Great: If you consider yourself a wine enthusiast, this private tour is a dream come true. After meeting your driver at Livorno Port, you’ll enjoy a 90-minute scenic drive to Greve in Chianti, the heart of the Chianti Classico region. Once in Greve, explore the charming Piazza Matteotti, known for its local shops, wine stores, and the renowned Falorni. Next, drive through the stunning SS 222 Chiantigiana, a road lined with vineyards and olive trees, on your way to Panzano in Chianti. Admire the hilltop village’s church and castle tower before heading to Fattoria di Montecchio winery. Here, you’ll tour the wine cellars, learn about wine and olive oil production, and taste Chianti wines like Chianti Classico and Super Tuscans. If Montecchio is unavailable, Casa Emma winery offers a similar experience. Optionally, stop at La Locanda di Pietracupa for an authentic Tuscan meal, or continue exploring the countryside’s picturesque villages before returning to Livorno Port.
• Pro Tip: Take some time to visit Enoteca Le Cantine, one of Tuscany’s largest wine shops

Why Take a Wine Tour from Florence?

Florence is not just a hub of art, culture, and Renaissance beauty—it’s also the perfect launching point to explore Tuscany’s famed wine regions. You could rent a car and drive yourself, but honestly, why deal with the hassle of navigating winding roads when you could sit back, relax, and focus on wine tasting?

 

Wine tours take the stress out of the equation. They’ll shuttle you to some of the best vineyards, arrange tastings, and give you the inside look on Chianti’s history, winemaking traditions, and what makes the wines here so special. And yes, you’ll taste a lot of wine—but that’s the whole point, right?

Where to Stay in Florence and Chianti

Finding the right place to stay can make or break your trip. We extensively covered the topic of Tuscany cozy villas near wineries for a dream getaway in our article. But, here are our personal picks for where to stay if booking some of the recommended wine tours from Florence.

In Florence

• Hotel Lungarno: Stylish hotel with stunning views of the Ponte Vecchio.
• Villa Cora: A luxurious escape just outside the city center, with a beautiful pool.
• Hotel Brunelleschi: Located right in the heart of Florence, with incredible views of the Duomo.
• Palazzo Vecchietti: Boutique hotel with personalized service and an intimate feel.
• The St. Regis Florence: Historic luxury right on the Arno River.
• Four Seasons Florence: An oasis in the city with an impressive private park.
• Il Salviatino: Gorgeous villa with incredible views over Florence.
• Portrait Firenze: Stylish and modern, offering spacious suites.
• Hotel Savoy: A classic Florentine hotel with a chic atmosphere.
• NH Collection Firenze Porta Rossa: For a touch of history, this hotel is housed in a 13th-century building.

In Chianti

• Castello di Spaltenna: A stunning castle turned hotel, right in the middle of the vineyards.
• Borgo San Felice: A charming vineyard village with luxurious accommodations.
• Villa Bordoni: Cozy, family-run with great food and lovely rooms.
• Relais Vignale: Located in Radda in Chianti, with beautiful views and a relaxed vibe.
• Le Fontanelle: A luxury retreat nestled among the hills.
• Castello di Verrazzano: Stay at this historic castle and immerse yourself in the winemaking process.
• Villa Le Barone: Romantic and serene, surrounded by olive groves and vineyards.
• Locanda Le Piazze: A small, boutique hotel with chic rooms and a lovely pool.
• La Petraia: A farm stay with an emphasis on sustainability and organic living.
• Il Borgo di Vescine: A medieval hamlet turned luxurious retreat.

Where to Eat in Florence and Chianti

You can’t experience Tuscany without indulging in its food. These are my top restaurant picks that showcase the best local flavors.

In Florence

• Osteria del Cinghiale Bianco: Rustic and authentic, with hearty Tuscan dishes.
• Trattoria Mario: A lively spot with amazing bistecca alla fiorentina.
• Il Santo Bevitore: Contemporary and creative, but rooted in tradition.
• Cibrèo: For traditional Florentine fare with a gourmet twist.
• La Giostra: Romantic atmosphere and incredible pastas.
• Trattoria Sostanza: Famous for its butter chicken and cozy ambiance.
• Ora d’Aria: Michelin-starred restaurant with modern Tuscan cuisine.
• Enoteca Pinchiorri: For a splurge-worthy dining experience and an outstanding wine list.
• Il Palagio: Fine dining in a luxurious setting at the Four Seasons Hotel.
• Trattoria 4 Leoni: A classic spot for traditional Tuscan fare.

In Chianti

• Ristoro di Lamole: Perched on a hill with breathtaking views and delicious food.
• La Bottega del 30: A Michelin-starred restaurant with impeccable flavors.
• Osteria Le Panzanelle: A cozy spot for authentic Tuscan dishes.
• La Cantinetta di Rignana: Rustic charm and a lovely terrace.
• Il Ristoro di Ama: Located at Castello di Ama, offering exquisite food and wine pairings.
• Osteria di Passignano: Michelin-starred with a focus on local ingredients.
• Ristorante Malborghetto: Family-run, with a warm atmosphere and traditional dishes.
• Enoteca Falorni: Great wine selection and tasty local specialties.
• La Torre at Castello di Spaltenna: Fine dining with a view.
• Dario Cecchini: For an unforgettable steak experience from the famous butcher of Panzano.

Wineries to Visit in Chianti

 

The Chianti region is home to some of the most prestigious wineries near Florence, and some of the best wineries to visit in Tuscany (in our humble opinion!). But, here is our take on the top ten famous wineries that offer tours and tastings that you might want to visit while you’re in Florence.

 

• Castello di Ama: Known for its art installations and exceptional Chianti Classico wines.
• Antinori nel Chianti Classico: Stunning modern winery producing world-class Supertuscans.
• Castello di Brolio: One of the oldest estates in Chianti with historic cellars.
• Fèlsina: A top producer of Chianti Classico and olive oil.
• Isole e Olena: Famous for its flagship wine, Cepparello, a cult favorite.
• Castello di Volpaia: A medieval village turned into a winemaking haven.
• Fonterutoli: Produces bold and expressive Chianti Classico wines.
• Castello di Verrazzano: Offers a full experience with wine, food, and incredible views.
• Fontodi: Organic wines with a focus on sustainability and quality.
• Badia a Coltibuono: A historic estate with a serene atmosphere and delicious wines.

What to Do in Florence and Chianti

Aside from wine and food, there’s so much to see and do in the region. Here are our top recommendations for making the most of your time:

In Florence

• Uffizi Gallery: A must for art lovers, home to works by Botticelli, Michelangelo, and more.
• Duomo di Firenze: Climb to the top for breathtaking views over the city.
• Ponte Vecchio: Wander across this iconic bridge lined with jewelry shops.
• Piazzale Michelangelo: The best spot to take in panoramic views of Florence.
• Bargello Museum: A hidden gem with an impressive collection of sculptures.
• Boboli Gardens: A peaceful escape with lush greenery and Renaissance statues.
• Accademia Gallery: Visit Michelangelo’s David in person.
• Santa Croce Basilica: Burial place of famous figures like Michelangelo and Galileo.
• San Lorenzo Market: Browse local produce, meats, cheeses, and more.
• Fiesole: Take a quick trip to this hillside town for ancient ruins and incredible views.

In Chianti

• Greve in Chianti: Wander the charming streets and visit the weekly market.
• Castellina in Chianti: Explore this medieval town with its picturesque center.
• Panzano: Visit the famous butcher Dario Cecchini and sample his legendary steaks.
• Radda in Chianti: Enjoy the laid-back vibe of this hilltop town and its beautiful views.
• Monteriggioni: A tiny walled town with a rich history.
• Abbazia di San Galgano: Visit this stunning, roofless abbey in the countryside.
• Volpaia: A picturesque village known for its wine and olive oil production.
• Brolio Castle: Tour the castle and learn about the history of the Chianti Classico region.
• Gaiole in Chianti: Another charming town with access to several top wineries.
• Wine Tastings and Cooking Classes: Spend a day learning to cook traditional Tuscan dishes and pairing them with local wines.

Final Thoughts

Going on a Chianti wine tour from Florence is an awesome way to witness first-hand the beauty and flavors of Tuscany. For more tips, you can check out our article on the best cooking classes and wine pairing in Tuscany. If you need a guide to the Tuscan wine region, we’ve got you covered in another article. We’ve also written about the best wine shops and wine bars in Tuscany if you plan to visit and purchase or taste some wines there. Plus, we’ve got all the info on the best vineyards and wineries to stay in Tuscany.

 

We hope our recommendations help you plan the perfect trip, filled with incredible wine, unforgettable meals, and stunning countryside views.

 

Cheers!