12 Best Tuscany Wine Tours from Florence for 2024

1. Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

⭐️ RATING: 5/5 Stars | ⏳ LENGTH: 11-12 hours | ✅ Book it!

Tuscany, Italy is a region that has it all. The Italian region is steeped in history, is full of delicious food and has a breathtaking landscape of rolling hills.

If you are visiting Italy, you must take the time to explore this area, especially to try the wine. This Chianti wine tour from Florence offers to show you the highlights as a local guide takes you around Siena, San Gimignano and Pisa. 

You will get to see the sights of Siena before heading to an organic vineyard. Here you will sample a delicious 3 course Tuscan lunch with accompanying wines. Next, you will head to San Gimignano and Pisa where you can view the famous Leaning Tower of Pisa. 

Olga says, “Everything was great including our guide Manolo and bus driver Lorenzo! Manolo is the best 👌! And very informative. Highly recommended. Money well spent.”

Your first stop for this small-group Tuscany wine tasting tour from Florence will be Siena. Enjoy a guided tour around the Italian city and admire the Gothic architecture of the Siena Cathedral. After this, you will board your coach which will take you to the rolling Tuscan hills.

Arrive in the Chianti wine region where you can take a leisurely stroll through grape lined vineyards and beautiful olive groves. You will get to enjoy a traditional Tuscan lunch with bread, cold cuts of meat, salad and pasta. All washed down with a wine tasting experience. 

Next on the itinerary is San Gimignano. Wander the cobbled streets, marvel at the medieval towers and explore the historic squares. Make sure you grab some gelato when you are here, it is delicious! The final stop of the day is Pisa, where you will venture to the Pisa Baptistry, the Pisa Duomo and the Leaning Tower of Pisa. 

Important details

• Start time: Check in at 7:45 am to depart at 8 am from Piazza della Stazione.
• Duration: 11 to 12 hours 
• Includes: Air-conditioned vehicle. Professional English speaking tour guide with you for the whole day. Guided walking tour of Siena with entrance fee to the cathedral. Hearty farmhouse lunch (veggie and gluten-free options available). Wine tasting of four varieties. Free time to explore the towns at your own pace.

2. Small-Group Wine Tasting Experience in the Tuscan Countryside

⭐️ RATING: 5/5 Stars | ⏳ LENGTH: 4 hours 45 minutes | ✅ Book it!

If you are looking for half-day wine tours from Florence, then this could be the perfect one. Have the chance to explore the Chianti Classico region, take part in a four hour wine tasting experience and visit two of the top rated wineries in the area.

You will be able to explore the wine cellars, learn how the wine is made and taste multiple wines and olive oil. The tour also includes local delicacies such as bruschetta and fresh Italian cheeses. 

Bonnie says, “We enjoyed tasting the wine and snacks and enjoyed the stories about the wine, the area, and traditions. The vineyards and villa were beautiful.”

This Chianti wine tour will take you to two different wineries in the Chianti Classico hills. At the first stop you will be able to enter the production areas and learn how to the wine is produced, wander through the picturesque vineyards and also enter the barrel room. This is then where you will get to sample the local Italian wine in a fun wine tasting of three wines. There is also a chance to try the locally made olive oil.

The next stop is the second winery where you can roam the estate and tour the production areas. Another wine tasting will take place where you can sample three more wines. These will be perfectly paired with cheeses, olive oil, cold cuts of meats and other Tuscan specialites. At the end of the trip there is a wine shop you can browse for souvenirs. 

Important details

• Start time: Check in at 8:45 am if booked for 9 am or 2:15 pm if booked for 2:30 pm from Piazzale Montelungo.
• Duration: 4 hours 45 minutes. 
• Includes: Small-group tour (max. group size 25 people.) Transport by air-conditioned vehicle with free wi-fi on board. Professional and informative English-speaking driver/guide to lead you through the experience. Guided visit to 2 different wine estates. Tasting of 3 wines and olive oil at the first winery. Tasting of 3 wines and olive oil at the second winery paired with local Tuscan specialities (cheese, salami, cured ham and bruschetta).

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

⭐️ RATING: 5/5 Stars | ⏳ LENGTH: 9 hours | ✅ Book it!

This is one of the best wine tours from Florence. Not only do you get to visit two wineries, sample wine and cheese but also enjoy a 4×4 off roading expereince. Departing from Florence, you will be taken through the Tuscan countryside by a 4×4 off-road vehicle.

When you arrive at your destinations, you will get to explore a winery, estate, historic villa and a wine cellar. Take part in wine tastings that are paired with Italian extra-virgin olive oil and cheeses. The day finishes off with a tasty 3 course Tuscan meal. The restaurant has stunning views of the surrounding countryside. 

Sarah says, “Chianti Safari is a MUST DO! We had an incredible experience. Lavie is extremely knowledgeable about the area and the wine making process. We have never done anything like this and I would 1000% do it again. This shows you Tuscany from a whole new view. You truly can’t even express the breathing taking views! Our driver Roberto was fantastic as well!”

Begin your wine tour day trip by travelling through the rolling hills of Chianti. The first stop of the day is at a highly rated winery, Villa le Corti. You will spend a few hours exploring the wine estate. Take part in an exciting guided tour that takes you through the wine cellars, underground tunnels, olive mill and beautiful gardens. After this, sit back and relax as you are treated to a wine tasting with three wines, cured meats and two olive oils. 

The next stop on the tour is another winery restaurant named Località Rignana. Here, you will receive a 3 course meal where your plate will be filled with traditional Italian pastas. Of course, the fine Chianti wine will be flowing to accompany your meal. All with stunning views as your backdrop. 

The final stop on your wine tour experience takes you to Poggio Torselli. This smaller winery boasts two award winning varieties of wine that you will be able to sample in the afternoon’s wine tasting. You will tour the grounds of the winery, gaze at the unique villa on site and soak up the surrounding countryside. 

Important details

• Start time: Meet at 9 am from Piazza dei Cavalleggeri.
• Duration: 9 hours. 
• Includes: Transport by air-conditioned 4×4 vehicle. Professional guide. 9 samples of wine. 2 samples of olive oil. Food tastings and lunch.

4. Florence Sunset Walking Tour with Wine & Food Tasting

⭐️ RATING: 5/5 Stars | ⏳ LENGTH: 3.5 hours | ✅ Book it!

Florence is a beautiful Italian city waiting to be explored. It has a rich culinary heritage and many traditions and quirks waiting to be discovered.

If you are looking for wine tasting Florence city centre, then this sunset walking tour is a fantastic option. This tour has several elements to it including exploring the streets of Florence, tasting wine and learning all about Italian food. 

Discover Florence’s Official Wine Windows, explore a centuries old wine cellar and taste some of the best Tuscan wines on offer. You will also get to dive into the food scene where a local chef will serve you delicious pasta and traditional Tuscan soup.

Learn all about Florence’s most famous cocktail and make your own Negroni before eating some delectable Gelato, a must do in Florence!

Lauren says, “This was an amazing night. Eva was a wonderful guide and provided lots of information on wines, cheeses, meats, and other dishes. There was plenty of food and wine. We made wonderful friends with others in our group and all left the night feeling full and quite tipsy. Worth every penny and one of the highlights of our trip!”

Start off your evening wine tour in Florence by heading to Piazza Santo Spirito. Here you will cheer with a prosecco in hand before you begin your tour of Oltrarno, Florence’s coolest neighbourhood. On your first stop you will get to sample locally produced Italian cheese including one Parmigiano and two Pecorino.

Next up, enjoy the experience of a wine window. Here you will learn all about this quirky tradition in Florence, drink wine and eat bruschetta. You will pass by not one by two of the wine windows. The second wine window also serves an amazing charcuterie board that pairs great with their wine. 

Fiaschetteria, a traditional Italian wine shop is awaiting your next stop. Here you get to sample traditional Tuscan soup, a wild boar stew, a famous Negroni cocktail and of course some Super Tuscan wine. Learn all about ‘cucina povera’ which is the Tuscan zero waste cuisine and culture. 

You will then wander over to a traditional trattoria that uses new innovative cooking techniques. You will get to eat some pasta, prepared by the chef in front of you, along with some Chianti Classico. Followed by a quick course in real artisan gelato, can you spot the authentic varieties? 

Important details

• Start time: Meet at your booked time slot from Piazza Santo Spirito.
• Duration: 3 hours and 30 minutes.
• Includes: 14 samples at 6 different tasting locations. Negroni cocktail demo and drinking! Taste 5 amazing wines. Local english speaking guide. Florence – A food lover’s guide.

5. Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

⭐️ RATING: 5/5 Stars | ⏳ LENGTH: 6 hours | ✅ Book it!

If you want to experience the Chianti countryside in an alternative way, consider this Tuscany bike and wine tour. You will get to cycle through the Italian countryside with a breeze in your hair.

Witness the stunning scenery, olive tree lined paths and fertile land before heading to a 12th century castle. Here you will get to sample flavours that the Tuscan region has to offer such as Chianti wine and olive oil. A delicious lunch is also included in the tour. 

Caroline says, “My husband & I had a wonderful experience—such a great day trip from Florence! The tour guide was super friendly & knowledgeable, the views were beautiful (even with things just starting to grow, with it being earlier in the season), and the lunch + wine-tasting was delicious. At the end you have the opp to buy wine & olive oil, which we definitely did.”

This bike tour will create memories to last a lifetime. You will be dropped off in the countryside where your adventures begin. From here, ride along countryside paths that are lined with beautiful olive trees, vineyards and Italian villas.

Your amazing tour guide will ensure you get the best expereince possible as you travel through the Chianti region. There will be plenty of opportunities to stop, take a break and snap some photos of the breathtaking landscapes. 

You will then stop at one of the villas, where you will enjoy a light lunch. This will be accompanied by an olive oil and wine tasting experience. You will also have the opportunity at the end to purchase souvenirs to take home with you. 

Important details

• Start time: Meet at 8:30 am from Via Ghibellina.
• Duration: 6 hours.
• Includes: Round trip transport from Florence to our starting point in the countryside. Engaging, fun and professional tour guides. Wine and extra virgin olive oil tasting with the option to purchase them. Bike and helmet. Bike orientation and safety briefing. Approximately 2 hours bike ride. Eat at a Tuscan villa: light lunch is offered with wine and extra virgin olive oil tasting.

6. Chianti Wineries Tour with Tuscan Lunch and San Gimignano

⭐️ RATING: 5/5 Stars | ⏳ LENGTH: 8 hours | ✅ Book it!

This is easily one of the best Tuscany wine tours from Florence. The tour includes round trip transportation with a knowledgeable tour guide. This means stress free day with no hassle, just memories and lots of wine tasting!

Explore the famous Chianti wine region where you will learn all about the traditions of the Italian wine making process. You will get to enjoy a fantastic wine tasting expereince all with an authentic Tuscan lunch.

Rose says, “The driver Daniel was excellent! The tastings were amazing and we had such fun with the other couples.”

Throughout the course of this full day wine tour, you will visit two different wineries in the Tuscan hills. Here you will enjoy a wine tasting experience and dine on a traditional Tuscan meal. You will get to visit and walk around the streets of San Gimignano, a medieval village located in the Chianti region.

Here you will be taken to the local museum, SanGimigano1300 where you can learn all about the history of this village. Enjoy strolling around the streets, the historic squares and eat incredible Italian gelato. Make sure to take in the wonderful panoramic views as the village is built on a hilltop. 

The final stop on the tour is a visit to Piazzale Michelangelo. In the centre of this plaza, you will find a replica of Michelangelo’s Statue of David, with a backdrop of the below Renaissance city.

Important details

• Start time: Meet at 9 am in front of Cafe’ Gamberini.
• Duration: 8 hours.
• Includes: Transport by air-conditioned comfortable minivan. Lunch. Wine tastings. A visit of two wineries. Wine cellar and vineyards tour. Live commentary on board. A guided visit of San Gimignano. A visit to Michelangelo Square.

7. Essence of Chianti Small Group Tour with Lunch and Tastings from Florence

⭐️ RATING: 5/5 Stars | ⏳ LENGTH: 8 hours | ✅ Book it!

This wine tour in Tuscany from Florence takes you to three wineries in the Chianti region. Throughout the course of the day you will explore various wine cellars, vineyards and wine estates.

Furthermore, you will satisfy your thirst with a variety of wines to taste and sip, learning the different notes and flavours in each. At midday, savour a delicious Tuscan lunch with local products including salami, cheese and bruschetta. To end the day you will have the chance to explore the medieval village of Greve. 

Paul says, “Leonardo was fantastic Knowledge and humor all rolled into one. That and the beautiful scenery made it an unforgettable trip.”

The first winery on this full day tour is Fattoria di San Michele a Torri. The estate is a whopping 370 hectares of land, built on a hilltop in the Classic Chianti and Chianti Colli Fiorentini countryside. Enjoy a lovely morning at this estate whilst you tour the vineyards and sample their wines and olive oil. 

Afterwards, head to Greve, a classic Italian countryside village. You have time at leisure to wander the streets, explore the local shops and admire the Piazza Matteotti. After a while, hop back in your transport which will take you down Chianti Road. This is the most famous Tuscan wine road. You will see miles and miles of olive trees, rows of grapes in vast vineyards and lots of green rolling hills. 

Your second winery experience is based at Casa Emma. This will be an educational visit where you will learn about the traditions of their wine making process, the history of the estate and their top tips and secrets to making their famous Chianti red wine and olive oil. Once the tour is over, sit back and enjoy a tasty lunch with a side of their Riserva, Super Tuscans and Chianti Classico wines. 

To round off the trip, you will stop at Villa Poggio Torselli. The final winery of the day. This is family owned and is surrounded by stunning landscaped Italian gardens. 

Important details

• Start time: Meet at 9 am in front of Cafe’ Gamberini.
• Duration: 8 hours.
• Includes: Small group tour: no crowds and more personalized experience. Transportation by air-conditioned and fully equipped vehicle. Free wi-fi on board. Professional and informative English speaking driver/guide to lead you through the experience. Quick stop to see Greve in Chianti, the most representative Village of the Chianti Classico area. Guided visit to 3 wineries, tasting of great wines, olive oil and more. Typical Tuscan lunch: assorted cold cuts, cured ham, salami, cheeses, bruschetta, pasta (usually handmade pasta), and dessert.

12. Half day Chianti Vineyard Escape from Florence with Wine Tastings

⭐️ RATING: 4/5 Stars | ⏳ LENGTH: 4 hours | ✅ Book it!

The Tuscan countryside is famous for its Chianti wine region and the wine that it produces. You can get a glimpse of this famous beauty with this half day wine tour from Florence.

You will visit two local wine estates where you will be taught the traditions of wine making and sample the wines that they produce. Furthermore, indulge in authentic Italian snacks such as bruschetta and cheese.

Jane says, “Driving through the Tuscan countryside and being able to taste a few wines without having to worry about driving. The guide was fabulous and friendly.”

Journey through the Chianti countryside where your tour guide will comment with interesting facts and stories of the region. Enjoy the views from Chianti Road and learn all about Gallo Nero (Black rooster).

You will visit two different wine estates on the trip. At each winery stop off for a wine tour and tasting where you will get to try the local delicacies. Try 3 to 4 different wine varieties at each winery along with some balsamic vinegar, local olive oils and cheese. During your visits, you will be taken out into the vineyards to appreciate the surrounding beauty of the Tuscan hills. 

Important details

• Start time: Meet at your booked time slot at Piazzale Montelungo.
• Duration: 5 hours.
• Includes: Journey by fully-fitted GT Coach with Free Wifi on board. English only tour leader. Visits of two charming wine estates with tour of the wine cellars and its vineyards. Sampling of up to 3-4 different types of wines at each winery and extra-virgin olive oil. Tasting of delicious regional products during the wine tastings. Panoramic stops along Chianti roads to take amazing pictures. Possibility of buying wine, oil, balsamic vinegar and other regional products.