7 Best Wine Tours from Florence (by a Local)

Florence is famous for Renaissance art, beautiful churches, and some of the best food in Italy. But one of the best parts of visiting the city is how easy it is to escape into the Tuscan countryside for a day of wine tasting!

I was born and raised in Bologna, just about an hour north of Florence, so I’ve been to the city more times than I can count. I wouldn’t call myself a Florentine, but I do know the area very well.

And Tuscany? I’ve explored it many times over the years, from Chianti wineries to hilltop towns and those classic cypress-lined roads you see in every postcard. Wine tasting here is one of those experiences that really does live up to the hype.

Taking one of these wine tours from Florence is also the easiest way to enjoy the region without worrying about driving, booking wineries, or figuring out countryside logistics on your own.

To help you choose, I’ve rounded up the best options below, from classic Chianti tastings to private wine tours, Brunello experiences, and even an e-bike tour through the hills.

I usually book tours through Viator and GetYourGuide because they offer reliable operators and flexible cancellation policies. Most tours can be canceled up to 24 hours in advance for a full refund.

Best Wine Tours from Florence: Quick Picks

Short on time? These are the wine tours from Florence I recommend most:

OUR PICK: Best Wine Tour from Florence

Duration: 7 to 9 hours
Type: Small-group wine tour
Best for: First-time visitors who want the most complete Tuscany wine experience from Florence

This Small-Group Wine Safari: Tuscany Wine Tasting Tour from Florence is my top pick because it gives you a proper day in the Tuscan wine country, without making you organize wineries, transport, lunch, or tastings yourself.

One important thing to know before booking: this tour page has a few different options. Some versions focus on two wineries, while the Full-Day Wine Safari is the one I recommend if you want the most complete experience. That is the version with the 4×4 vehicle, several tastings, a Tuscan meal, and a longer day in the countryside.

You’ll meet your guide in central Florence, near Santa Maria Novella train station, and board a customized air-conditioned 4×4 vehicle. This is one of the details that makes the tour more fun than a standard coach trip, as you’ll follow scenic countryside roads and off-road routes through vineyards, olive groves, and rural Tuscany.

The first stop is usually a boutique winery, where you’ll taste wine paired with local products such as cured meats and extra virgin olive oil. You’ll also visit the historic underground wine cellars, which give you a better idea of how wine is produced and stored in the region.

After that, you’ll continue through the countryside to a Tuscan winery restaurant. This is where you’ll sit down for a proper 3-course meal, usually with regional dishes such as fresh pasta, paired with more local wine. This is a big reason I like this tour: it feels like a real Tuscan lunch, not just a quick snack between tastings.

The day continues with a drive through more Tuscan countryside before the final winery stop. Here, you’ll tour the winery or grounds, learn more about the estate’s production, and enjoy a final tasting of three wines paired with cheese.

By the end of the tour, you’ll have visited multiple wine locations, tasted several wines, tried olive oil and local food, explored cellars, enjoyed a proper meal, and seen a lot of the countryside around Florence, all without needing to drive.

Just double-check the option you select when booking. If you specifically want the longer, more complete experience, choose the Full-day Wine Safari. If you choose the Brunello or Val d’Orcia-style option, the route may go farther into southern Tuscany and focus more on those famous red wines instead.

Why this is the best tour

This is the best wine tour from Florence because it feels like a full Tuscan countryside experience, not just transportation to a tasting room. You get wine, food, scenery, estate visits, cellar tours, olive oil, and the 4×4 element all in one day.

Compared to the shorter Chianti tours, it’s much more complete. Compared to the Tuscany sightseeing day trips, it stays more focused on wine. That makes it the best middle ground if you want a beautiful, generous, wine-centered day from Florence.

Read what the reviews say:

“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 breathtaking views!”

Sarah_A – Read more reviews

This tour includes transportation by 4×4 vehicle, an English-speaking wine expert guide, several wine tastings, extra virgin olive oil tastings, cheese and salumi tastings, and a traditional Tuscan lunch or dinner. ➥ BOOK IT HERE

Half-Day Wine Tours from Florence

Small-Group or Semi-Private Chianti Wine Tasting Tour

Duration: 4 hours 45 minutes
Type: Small-group or semi-private wine tour
Best for: Travelers who want a classic Chianti wine tasting with the option to upgrade to a smaller group

This Small-Group Wine Tasting Experience in the Tuscan Countryside is a great option if you want to visit Chianti but don’t have a full day to spare.

When booking, you can choose between the small-group tour, which has a maximum of 25 people, and a semi-private option, which is limited to 8 people. I wouldn’t call 25 people tiny, but it’s still much better than a large coach tour. If you want a more personal experience, I’d choose the semi-private option.

You’ll travel from Florence into the Tuscan countryside and visit two wine estates. Along the way, you’ll learn about local winemaking, walk through cellars, and taste 3 wines in each winery paired with small bites like cheese, cured meats, olive oil, and bruschetta.

It’s short, easy, and focused on wine, which makes it a very good choice if your Florence itinerary is already packed.

Pros

• Clear half-day option
• Visits two wineries in the Chianti area
• Semi-private upgrade available with a maximum of 8 people

Cons

• The standard “small-group” version can have up to 25 people
• No full lunch included
• Less immersive than a full-day wine tour

This tour includes transportation, a guide, visits to two wine estates, wine tastings, olive oil, and local food pairings. ➥ BOOK IT HERE

Chianti Wineries Tour with Wine Tasting from Florence

Duration: 5 to 5.5 hours
Type: Group wine tasting tour
Best for: Travelers looking for the best-value half-day wine tour from Florence

If price matters, this Florence: Chianti Wineries Tour with Wine Tasting is the one I’d look at first. It’s usually much more affordable than many other wine tours from Florence, while still taking you into the Chianti countryside.

You’ll visit two local wineries, taste several wines (3-4 at each stop), and try Tuscan products such as olive oil, balsamic vinegar, bread, and salami. It’s not as intimate as some smaller tours, but it gives you a proper taste of Chianti without a big splurge.

This is the tour I’d choose if you want the wine-country experience but don’t want to spend top-pick prices.

Pros

• One of the best-value Chianti wine tours from Florence
• Visits two wineries
• Good option for a simple half-day countryside escape

Cons

• Less personal than a small-group or private wine tour
• It can feel a little more structured and group-oriented

This tour includes transportation, a guide, visits to two wineries, wine tastings, and local product tastings. ➥ BOOK IT HERE

Tuscany Day Trip from Florence with Wine Tasting

Duration: 12 hours
Type: Tuscany day trip with wine
Best for: Travelers who want to see Siena, San Gimignano, Pisa, and enjoy a winery lunch in one day

This Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery is not a pure wine tour, and I want to be clear about that. It’s more of a full Tuscany sightseeing day trip with a winery lunch and wine tasting included.

You’ll leave Florence in the morning and spend the day visiting some of the most famous places in Tuscany. The itinerary includes Siena, where you’ll join a guided walking tour, then a stop at a Chianti organic family-run wine estate for a Tuscan lunch paired with wine and a wine tasting.

After lunch, the tour continues to San Gimignano, one of Tuscany’s prettiest hilltop towns, known for its medieval towers. You’ll also visit Pisa, where you’ll have time to see the Leaning Tower and the surrounding square (you can upgrade your ticket to include tickets to the tower).

It’s a long and busy day, but it works well if you want the classic Tuscany checklist: historic towns, countryside views, a winery stop, lunch, and wine, without planning all the transfers yourself.

Pros

• Combines several major Tuscany highlights in one day
• Includes winery lunch and wine tasting
• Great choice if you want more than just wineries

Cons

• It’s not a dedicated wine tour
• The day is long and quite packed

This tour includes transportation, a guide, Siena, San Gimignano, Pisa, lunch at a winery, and wine tasting. ➥ BOOK IT HERE

Private Wine Tour from Florence

Duration: 8 hours
Type: Private wine tour
Best for: Couples, families, and travelers who want a more comfortable wine experience

This Private Tuscany Wine Tour Experience from Florence is the best option if you want the countryside experience without joining a group tour.

You’ll be picked up at your hotel and head into the Tuscan countryside with a private guide and driver. The day usually includes 3 wine estates, tastings, olive oil, cellar visits, and a full Tuscan lunch paired with wine.

This is especially good if you’re traveling as a couple, with family, or with friends and want a more relaxed pace. It also gives you more room to ask questions and enjoy the wineries without feeling rushed.

Pros

• Private experience with hotel pick-up and drop-off
• More comfortable and flexible than a group tour

Cons

• More expensive than group wine tours
• Best value if you’re traveling with more than two people

This tour includes hotel pick-up and drop-off, a private guide, wine tastings, and lunch. ➥ BOOK IT HERE

Brunello Wine Tour from Florence

Duration: 10 hours 30 minutes
Type: Small-group wine tour
Best for: Wine lovers who want to go beyond Chianti

If you’re more interested in Brunello and Val d’Orcia than classic Chianti, this Val d’Orcia Brunello Wine Tour with Montalcino and Montepulciano is the one to choose. It takes you farther south than most wine tours from Florence, into one of the most scenic wine regions in Tuscany.

The day starts Florence, where you’ll meet your English-speaking driver and head toward Montalcino. Your first real stop is a family-owned winery, where you’ll learn about Brunello di Montalcino, from vineyard techniques to the winemaking process and aging. Of course, you’ll also taste different vintages of Brunello.

After the winery, you’ll make a quick stop at the Fortezza di Montalcino and the tiny town center before continuing to Pienza, a gorgeous hilltop town. Here, you’ll enjoy a 3-course lunch with wine, usually in the garden of a former 15th-century convent with views over the Val d’Orcia.

After lunch, you’ll have free time in Pienza. Then the tour continues to Montepulciano, where you’ll visit a historic cellar known as the “underground city”. The final wine tasting takes place at the exit of the underground cellar, with wine and other local food specialties.

Pros

• Great option for Brunello and Vino Nobile lovers
• Visits the Val d’Orcia, one of Tuscany’s most beautiful areas
• More interesting than another standard Chianti tour

Cons

• Longer travel time from Florence
• Not the best choice if you only want a quick wine tasting near the city

This tour includes transportation, visits to Montalcino, Montepulciano and Pienza, wine tastings, and lunch. ➥ BOOK IT HERE

Active Wine Tour from Florence

Duration: 6 hours
Type: Guided e-bike tour with wine tasting
Best for: Active travelers who want to explore the Chianti hills by bike

This Chianti Hills E-Bike Tour with Tuscan Lunch & Two Wine Tastings is the best option if you want a wine tour that feels more active and outdoorsy.

You’ll meet in central Florence, get your e-bike and helmet, and start riding out of the city with your guide. The route takes you toward the Chianti hills, passing countryside views, vineyards, and small villages along the way.

The e-bike helps with the hills, but this is still not a lazy ride. You should be comfortable cycling, including through some city traffic at the beginning and on countryside roads later.

During the tour, you’ll stop at a local winery for a Tuscan lunch and wine tasting. The sample menu includes Tuscan cold cuts, crostini, local cheeses, pasta, and dessert. After the countryside ride, the guided option also includes a second wine tasting in Florence.

Important: Make sure you choose the guided option when booking. The tour page also has a self-guided option, but for that version, the guide, lunch, and wine tastings are not included. So if you want the full experience, don’t accidentally book the wrong one.

I’d pick this tour if you like the idea of combining cycling, countryside views, wine, and lunch in one experience. It’s a fun alternative to sitting in a van all day, but it’s best for people who are confident on a bike.

Pros

• More active and scenic than a standard wine tour
• Includes a winery lunch and two wine tastings if you choose the guided option
• Small-group format, with the tour page listing up to 12 participants in the inclusions

Cons

• You need to be comfortable riding a bike
• The route starts in the city, so you may ride near traffic before reaching the countryside
• The self-guided option does not include the guide, lunch, or wine tastings

This tour includes e-bike rental, helmet, insurance, a local tour leader, a scenic Chianti route, a winery lunch, wine tasting, and a second wine tasting when the guided option is selected. ➥ BOOK IT HERE

Is It Worth Taking a Wine Tour from Florence?

In my opinion, yes. You can rent a car and visit wineries on your own, but wine tasting in Tuscany is one of those experiences where a tour makes life much easier.

You don’t have to worry about driving after tastings, booking winery visits, or choosing where to go. This is especially useful in Chianti, where many wineries are spread out, and public transport is not very helpful.

If you only have a short time in Florence, I’d choose a guided wine tour. You’ll see more, drink more safely, and spend less time figuring out logistics.

FAQ: Wine Tours from Florence

What is the best wine region to visit from Florence?

Chianti is the easiest and most popular wine region to visit from Florence. It’s close to the city, beautiful, and full of wineries. If you have more time and love red wine, Val d’Orcia, Montalcino, and Montepulciano are also fantastic.

Can you visit wineries from Florence without a tour?

Yes, but it’s not always simple. Many wineries require reservations, and getting around without a car can be difficult. If you plan to drink wine, joining a tour is usually the easiest and safest option.

Are half-day wine tours from Florence worth it?

Yes, especially if you only want a taste of the Tuscan countryside. A half-day tour won’t feel as immersive as a full-day experience, but it’s a good way to visit wineries without giving up a whole day in Florence.

What should you wear on a wine tour in Tuscany?

Wear something comfortable but nice. You don’t need to dress up too much, but avoid heels because many wineries have gravel paths, cellars, or uneven ground. In summer, bring sunglasses, sunscreen, and a hat.

What if I want more than wine tasting?

If you want to visit Tuscan towns, countryside viewpoints, and maybe Pisa or Siena too, a broader Tuscany day trip might be a better fit. I have a separate guide to the best Tuscany tours from Florence for that.

Can you do a wine tour from Florence with only 2 days in the city?

You can, but I’d only do it if wine tasting is a real priority for you. If it’s your first time in Florence, I’d spend at least one full day in the city first. My 2 days in Florence itinerary can help you decide how much time you want to keep for museums, churches, viewpoints, and food before adding a countryside tour.

Interested in other foodie experiences in Florence? Check out my guides to the best food tours in Florence and the top Florence cooking classes.