🍷 The 7 Best Chianti Wine Tours From Florence [2024 Reviews]

Whether you’re a fan of Chianti wine or simply know of it due to its notoriety in a certain film, if you’re in Florence we highly recommend you check out where it originates from.

The famous dry, red wine can only be produced in this region of central Tuscany, with its cool hills and rich soil. While you could definitely rent a car and explore it on your own, if you want to maximize the experience we recommend a tour.

We’ve done the research for you, bringing you tours that are worth your time and money yet are varied enough that you have a nice selection to choose from.

If that sounds like fun to you, then check out these awesome Chianti wine tours!

Best Chianti Wine Tours From Florence

Chianti Safari: Tuscan Villas, Cheese, Wine & LunchPrivate Half-Day Chianti Tour & Wine Tasting From FlorenceSmall Group Chianti at Sunset Wine Tasting Tour from Florence

Best Adventure Tour

Best Half-Day Tour

Best Small Group Tour

editors choice
Chianti Safari: Tuscan Villas, Cheese, Wine and Lunch from FlorencePrivate Half-Day Chianti Tour & Wine Tasting From Florence
Small Group Chianti at Sunset Wine Tasting Tour from Florence
Departure:Piazza dei Cavalleggeri, 50122 FirenzeHotel pickup and drop-off includedPiazza dei Cavalleggeri, 50122 Firenze FI
Start:9:00 AM2:45 PM4:00 PM
Duration:9 hours4 hours4.5 hours
Includes:Transport by air-conditioned 4x4 vehicle, professional guide, 9 samples of wine, 2 samples of olive oil, food tastings, lunchGuide, private vehicle at your disposal for a maximum of 4 hours, historical Chianti winery visit with wine tasting of five fine wines w/ local snacksCar or minivan - max 8 persons, expert guide, visit to a typical wine estate and wine tasting, 4 wines, oil, cheese with marmalade, chocolate vineyard tour

Tour Information & Booking

Tour Information & Booking

Tour Information & Booking


Quick Answer: The 7 Best Rated Chianti Wine Tours For 2024

  1. Best Adventure Tour: Chianti Safari – Tuscan Villas, Cheese, Wine and Lunch from Florence
  2. Best Half-Day Tour: Private Half-Day Chianti Tour & Wine Tasting From Florence
  3. Best Small Group Tour: Small Group Chianti at Sunset Wine Tasting Tour from Florence
  4. Best Private Tour: Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence
  5. Best Value Tour: Chianti Wine Tour with Lunch, Visit S.Gimignano, Organic Wineries and Much More
  6. Best Luxury Tour: Private Chianti Wine Tour Leaving from Florence
  7. Best Budget Tour: Chianti Vineyards Escape from Florence with Two Wine Tastings

Chianti Wine Tour Reviews

1. Best Adventure Tour: Chianti Safari: Tuscan Villas, Cheese, Wine and Lunch from Florence

Chianti Safari: Tuscan Villas, Cheese, Wine and Lunch from Florence

Tour Highlights:

  • Duration: 9 hours
  • Departure: Piazza dei Cavalleggeri, 50122 Firenze FI, Italy or hotel pickup and drop-off
  • Departure Time: 9:00 AM
  • Includes: Transport by air-conditioned 4×4 vehicle, professional guide, 9 samples of wine, 2 samples of olive oil, food tastings, lunch

Let’s start things off on the right foot with the Chianti Safari: Tuscan Villas, Cheese, Wine and Lunch from Florence. Who thought that safaris and off-roading would work so perfectly with cheese and wine?

This tour is so seamlessly-organized and melds adventure with relaxation and appreciation for the finer things in life wonderfully.

Start out by meeting your guide and the rest of your group at 9:00 am in the center of Firenze in the Piazzi dei Cavalleggeri. You’ll then be escorted onto the awesome 4×4 minibus that’s impossible to miss!

This bus is made for fun, yet ensures you’re comfortable with air conditioning, spacious seats, and large windows.

Why use a 4×4 vehicle?

Because you’re going to go off-roading, meaning you’ll get to see parts of Chianti that the vast majority of visitors don’t.

Stop first at Villa le Corti, owned by one of the most prominent Italian families. This gorgeous estate is located over a hillside and offers incredible views, but the real star of the show is the wine tasting!

Taste 3 of their wines meticulously paired with cured meats and 2 types of olive oils after taking a guided tour of their legendary wine cellars and olive mill by means of underground tunnels.

Next up it’s time to really buckle up and get ready for 4×4 fun over ancient woodland and those iconic Tuscan hills until arriving at LocalitĂ  Rignana where you’ll try even more tasty food and wine!

With your personable, knowledgeable tour you’ll be able to learn a lot in a way that’s unpretentious and welcoming.

Travel further into the hills and enjoy the vast countryside as you head to a smaller, more quaint winery called “Poggio Torselli”. By new means is this breathtaking place tiny, however!

These premium Tuscan ateliers will teach you all about their ancient traditions combined with innovation result in their award-winning wines.

More Information & Tour Booking

100% refund for cancellations within 24 hours of tour experience


Other Florence Experiences You May Enjoy:


2. Best Half-Day Tour: Private Half-Day Chianti Tour & Wine Tasting From Florence

Private Half-Day Chianti Tour & Wine Tasting From Florence

Tour Highlights:

  • Duration: 4 hours
  • Departure: Hotel pickup and drop-off included
  • Departure Time: 2:45 PM
  • Includes: English speaking driver, private vehicle at your disposal for a maximum of 4 hours, historical Chianti winery visit with wine tasting of five fine wines accompanied by local snacks

There are plenty of fantastic tours available on our guide, but not everyone has the availability for a full-day option. If that sounds like your situation, then check this next tour out.

The From Florence: Private Half-Day Chianti Tour & Wine Tasting is a 4-hour adventure that will take you through the beautiful Tuscan countryside and into some of the most respected vineyards in the world.

Limited to just 7 participants, this is a very small group tour where you’ll get plenty of one-on-one time with the guides and be able to ask any questions you may have.

This tour starts off by your guide/driver picking you up at your hotel in a private vehicle. The vehicles are always comfortable, with air-conditioning and plenty of room to stretch.

As you head along your journey, your driver will offer an introduction and educational commentary about each location and attraction that you pass.

The Montecchio winery is your first stop, where you’ll learn about their delicious Chianti Classico red wines. This historic estate is beautiful on its own, but you’ll get to try 5 amazing wines, including one first made back in the 13th century as a white wine!

Aside from your tour of the winery, you’ll also get to see plenty of thick woods, olive groves, medieval villages, Roman churches, classic farmhouses, and much more.

It’s hard to believe that so much majesty can be fit into a 4-hour tour, but thanks to supreme organization and obvious care for their customers, they manage to pull it off.

More Information & Tour Booking

100% refund for cancellations within 24 hours of tour experience


Search For Other Top Rated Florence Experiences You May Enjoy:


3. Best Small Group Tour: Small Group Chianti at Sunset Wine Tasting Tour from Florence

Small Group Chianti at Sunset Wine Tasting Tour from Florence

Tour Highlights:

  • Duration: 4.5 hours
  • Departure: Piazza dei Cavalleggeri, 50122 Firenze FI
  • Departure Time: 4:00 PM
  • Includes: Comfortable air-conditioned car or minivan – max 8 persons, expert English-speaking driver, visit to a typical wine estate and wine tasting, 4 wines, oil, cheese with marmalade, chocolate vineyard tour, dinner in restaurant is an available option

Next, we have the Small Group Chianti at Sunset Wine Tasting Tour from Florence. If you have a busy schedule during the daytime or are looking for another shorter tour, this is one to keep on your list.

Lasting 4.5 hours, you’ll try and learn about plenty of top-rated wines and tour through the Tuscan countryside.

In the afternoon, you’ll meet your driver/guide at the Piazza dei Cavalleggeri in the heart of Firenze which is easily accessible from anywhere in the city.

Set off in a comfortable vehicle and head along one of the most beautiful routes in the world: the Via Chiantigiana scenic route lined with cypress trees, extensive vineyards, medieval villages, and more. The first stop along the way is one of those medieval villages called Greve-in-Chianti.

Known for its triangular-shaped square, it was used as a meeting spot and location of their Saturday market for literally hundreds of years.

Stroll around these classic streets and marvel at the lovely construction, and local boutique shops. Head towards the main destination, taking a photo stop at Montefioralle.

Once you arrive to the vineyard, you’ll learn about their traditional techniques in their cellars, trying 4 of their top wines including the Chianti Classico and other “Super Tuscans”.

These tastings are so that they line up perfectly with the golden hour right before sunset, so you can snack on some delicious bruschetta and cheese while watching the light set over the vineyards.

After you get back in the vehicle, you’ll have time to stop in the charming village of Badia a Passignano for more photo ops, and learn all about its interesting history.

More Information & Tour Booking

100% refund for cancellations within 24 hours of tour experience


4. Best Private Tour: Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence

Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence

Tour Highlights:

  • Duration: 8 hours
  • Departure: Hotel pickup and drop-off included
  • Departure Time: 9:30 AM
  • Includes: Private luxury minivan, bottled water, onboard Wi-Fi (on request at reservation)

Next, we have another crowd favorite: the Private Tour in Siena, San Gimagnano and Chianti Day Trip from Florence.

This 8-hour tour is one of the most comprehensive of its kind, where you’ll see some of the most beautiful highlights of Tuscany.

This private tour allows for you to see more than the average traveler, and have your guide to yourself to ask questions and focus on what interests you most.

Start the tour off by meeting your guide at your hotel lobby around 9:30 am. You’ll then be escorted into the air-conditioned vehicle for the day, which will vary depending on the size of your group.

If you’re just going with a significant other or a couple family members, you may just go in a car or SUV while larger groups may go in a minivan.

Your first destination of the day is Siena, which is ever-popular due to its stunningly well-preserved medieval architecture which has earned it a UNESCO World Heritage title.

Rich in history and art, you’ll get to see some of its most famous landmarks such as the conch-shaped Piazza del Campo and 13th-century cathedral. Aside from that, take time to browse around the local shops or enjoy some local dishes at one of their many restaurants.

Next up is Castello Monteriggioni: a 13th-century walled city perfectly preserved, making you feel like you’ve been transported back to the Middle Ages. Here, you and your group will stroll around after lunch at one of the delicious local restaurants.

There’s an option to also have lunch at a farm or winery at Castellina In Chianti instead of extra time in these villages, where you can partake in wine tastings.

Then, your guide will lead you around the walled medieval town of San Gimignano located on rolling hilltops. Also known for its well-preserved architecture, their skyline is unlike any other in the world with tower houses emerging from said hills.

More Information & Tour Booking

100% refund for cancellations within 24 hours of tour experience


5. Best Value Tour: Chianti Wine Tour with Lunch, Visit S.Gimignano, Organic Wineries

Chianti Wine Tour with Lunch, Visit S.Gimignano, Organic Wineries and Much More

Tour Highlights:

  • Duration: 7 hours
  • Departure: Via Curtatone, 9, 50123 Firenze FI
  • Departure Time: 9:00 AM
  • Includes: Transport by air-conditioned confortable 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 of Michelangelo Square

If you’re looking for a tour that will fit into a tighter budget, we’ve just the thing. The Chianti Wine Tour with Lunch, Visit S. Gimignano, Organic Wineries is a full-day tour that will show you all around the Chianti wine region.

This is a fantastic way to get to know the area more in-depth without having to spend multiple days there. Start off by meeting your guide at 9 am in front of Café Gamberini in the center of Firenze, where you’ll board a spacious minivan.

These minivans are very comfortable, with air-conditioning, plenty of leg room, and large windows to offer unobstructed views of the beautiful Tuscan countryside.

Once you arrive at Fattoria Poggio Alloro, you’ll be taken on a fascinating guided tour of their cellars where you’ll learn about how they make theirs. Later, try a wine tasting of 4 to 5 wines with olives, cheeses, bruschetta, and more.

Then, try their extra virgin olive oil and learn about what makes a good one before heading out to pet some of the animals on their farm.

After, head over to San Gimignano where you’ll venture through the medieval architecture and stop at the 13th-century little museum, main squares, and learn about its history. Then, try some of the world-class gelato while taking in amazing 360 views of this iconic place.

Once at Tenuta Torciano, you’ll focus more on the traditional chianti wine, how they make it, and what makes it so special. After, enjoy a tasty 3-course meal with guided wine tastings of around 8 different types.

We particularly enjoyed trying their 30-year aged balsamic vinegar and extra virgin olive oil! We can’t forget the Piazzale Michelangelo, which is undoubtedly one of the most breathtaking places in all of Europe.

Overlooking the infamous renaissance city of Florence, you’ll see a replica of Michelangelo’s Statue of David located in the center of the square.

More Information & Tour Booking

100% refund for cancellations within 24 hours of tour experience


6. Best Luxury Tour: Private Chianti Wine Tour Leaving from Florence

Private Chianti Wine Tour Leaving from Florence

Tour Highlights:

  • Duration: 8 hours
  • Departure: Check with tour operator
  • Departure Time: 9:00 AM
  • Includes: Transportation on comfortable Mercedes Vclass minivan, fuel surcharge, 1 Wine tasting, driver/guide, private tour

Next up, is the Private Chianti Wine Tour Leaving from Florence. This is one of the best tours for wine lovers, as you’ll be spending the day heading through the Tuscan hills to medieval villages and legendary wineries.

If you have an entire day available, do yourself a favor and sign up for this educational, beautiful excursion!

This tour starts out at 9:00 am, where you’ll be picked up from your hotel or other accommodations. Focusing on comfort and luxury, transport will take place in a Mercedes V-Class minivan, with large windows for viewing and a smooth ride.

Take a short ride over to the countryside, until you reach the medieval village, Montefioralle. Come down the hill to Greve in Chianti, which is known for its triangular-shaped square that’s been used for important local events for hundreds of years.

Named for the river that runs through it, this lively market town is filled with fun shops and famous for being the capital of Chianti wine. The driver will take you to the central square, where you can explore it all!

Next, pass through the small village of Panzano, where you’ll visit a winery and have a guided visit of their cellars and vineyards. After, the owner will offer a tasting of their 3 most popular wines. If you’d like, you can choose to eat a relaxing lunch at that winery or at one of the best trattoria’s nearby.

Rocca di Castellina in Chianti is another must-see, where you’ll take some time for a relaxing stroll and let that delicious food digest.

There are some great wine shops here, though you’ll also be seeing another winery in town where you can compare and contrast their wines with the others you tried earlier in the day.

More Information & Tour Booking

100% refund for cancellations within 24 hours of tour experience


7. Best Budget Tour: Chianti Vineyards Escape from Florence with Two Wine Tastings

Chianti Vineyards Escape from Florence with Two Wine Tastings

Tour Highlights:

  • Duration: 5 hours
  • Departure: Piazzale Montelungo, Firenze FI
  • Departure Time: 8:30 AM & 2:30 PM
  • Includes: Round-trip journey by fully-fitted GT coach, multilingual escort, visits to two different wine estates with tours of wine cellars and vineyards, sampling of up to 3-4 Chianti wines at each winery, extra-virgin olive oil and balsamic vinegar

We wouldn’t be able to bring you the best tours while leaving out our next tour. The Chianti Vineyards Escape from Florence with Two Wine Tastings is simply incomparable if you’re looking for a budget-friendly option.

This is one of those “best bang for your buck” tours where you can escape the noisy city and learn all about traditional Chianti wines.

This 5-hour tour is also great if you have plans earlier in the day. Meet your guide at Piazzale Montelungo kiosk at the bus terminal. You’ll then board a luxe, fully-fitted GT coach and travel in style out to Tuscany’s rolling hills.

As you guys drive on, your guide will offer fascinating commentary on the history of the area, Chianti wine, and some fun anecdotes.

You’ll then arrive to your first rustic wine estate located right in the heart of the famous wine region. The first is a more quaint family winery, where the owner will tour you around the vineyards and cellars.

As you walk and explore, you’ll learn about how they came to be one of the most prominent producers of Chianti wine and what sets them apart from the competition before partaking in a wine tasting.

The next estate is much larger, though both are located on serene hilltops for top-notch views. Here, learn about their wine and compare them to the other vineyard’s as you try 5 different types.

We really enjoyed the pairing with local products like extra virgin olive oil, balsamic, and an array of cheeses. Then, you can take time to walk around the majestic landscape and bring along a glass of wine to accompany you on your stroll!

More Information & Tour Booking

100% refund for cancellations within 24 hours of tour experience


Planning Your Chianti Wine Tour From Florence

Best Wine Tours in Chianti

Can You Do a Chianti Wine Tour From Florence?

A wine tour in Chianti from Florence is a great idea if you looking to spend a day exploring the beautiful Tuscan countryside and taste some of the world’s most delicious wines.

The trip to Chianti from Florence is part of the experience itself. As you leave Florence and start seeing the picturesque hills of Tuscany and taking in the stunning scenery you will know why you came here! The rolling hills are covered in lush vineyards, olive groves and medieval towns that are frozen in time.

You’ll want to visit some of the region’s incredible wineries. Chianti is famous for its wine of course, especially its red wine made from the Sangiovese grape.

There are so many wineries it’s hard to know where to start! Each has unique wines and a tour you can do. Some of my personal favorites include Castello di Verrazzano, Fattoria di Montemaggio, and Castello di Brolio.

Of course Chianti is more than just wine. Make sure you take some time to explore the towns and villages that dot the landscape. Greve in Chianti is a particularly lovely town. It has a bustling market square and some fantastic restaurants serving up local specialties like wild boar ragĂą and pappa al pomodoro. Once you fall in love with the food, you should take a Tuscan cooking class in Florence.

Of course you can’t visit Chianti without taking in the breathtaking views. One of the best places to do this is from the Castello di Brolio. This medieval castle has been transformed into a winery and one of the most unique in Tuscany.

What Can I See on a Wine Tour in Chianti? (With a Sample Itinerary)

What Can I See on a Wine Tour in Chianti

Chianti is in the heart of Tuscany is well known for its vineyards, medieval villages and of course its Chianti wine. If you only have one day to explore you can still see plenty!

9:00 am – Start with a visit to the Castello di Brolio it’s a magnificent castle that has been owned by the Ricasoli family since the 12th century. Take a quick tour of the castle and the vineyard. You’ll also have the opportunity to taste some of the Ricasoli family’s award-winning wines.

11:00 am – Next, head to the charming town of Greve in Chianti. Check out the market and look for some souvenirs. Greve has some fantastic restaurants, try stop for a bite to eat. Try La Cantina del Gallo Nero for some delicious local cuisine.

1:00 pm – After lunch, drive to the Fattoria di Montemaggio, a family-run winery that produces some of the best organic wines in Chianti. Here you can take a tour of the vineyard and learn about how they make their wines.

3:00 pm – Head to the hilltop town of Radda in Chianti, which boasts stunning views of the surrounding countryside. Take a stroll through the town’s narrow streets and visit the Museo del Chianti.  It houses an interesting collection of artifacts related to the history of the region’s wine.

5:00 pm – End your day with a visit to the Castello di Verrazzano, a beautiful castle that dates back to the 12th century. Take a tour of the castle and its wine cellars, then do a tasting of their award winning wines.

There are so many things to see and do in Chianti that you could spend several days exploring the region. This one day itinerary will give you a small taste of Chianti.

What is the Best Way to do a Chianti Wine Tour From Florence?

Best Way to do a Chianti Wine Tour From Florence

Guided tour: The most convenient way is by taking a guided tour. We recommend the Private Tour in Siena, San Gimagnano and Chianti Day Trip from Florence. However there are many tour operators offering day trips to Chianti and they typically include transportation, wine tasting and a visit to a few hilltop towns.

Drive: You can rent a car and drive through the winding roads of Chianti. Be sure to bring a map and a good GPS. The roads can be quite confusing and are not well marked. Keep in mind the wine tastings might make driving back to Florence a bit challenging. Be careful you don’t indulge too much!

Bike or Vespa: If you’re feeling adventurous, you can take a Vespa tour around the vineyards or rent a bicycle and explore the region on two wheels.

No matter how you choose to explore the region, you should end your day trip with a delicious meal at a local restaurant. Chianti is famous for more than its wine there are plenty of restaurants to try! If you have the opportunity go to the Bistecca Alla Fiorentina!

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The Chianti Safari: Tuscan Villas, Cheese, Wine and Lunch is our Editors Choice for the best Chianti wine tour from Florence.

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Robert Baker

Robert is a content writer and editor at World Guides to Travel where he shares his love for the great outdoors. He also writes in-depth travel blogs for other websites around the world. Robert is passionate about the environment and uses his writing to educate people about the advantages and importance of sustainable living. Robert enjoys creative writing. In 2009, his children’s novel Sally Hemings & the Good Associates won the Children’s Fiction section of the You Write On Book of the Year Award.
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