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 with so many wine tours from Florence, it’s also easy to escape into the Tuscan countryside for a day of 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.

➥ Why trust me? I’m Italian, from Bologna, and I’ve spent over a decade helping travelers plan trips to Italy. I’ve explored Tuscany extensively and recently joined a Chianti wine tour to see the experience firsthand.

I usually book tours through Viator and GetYourGuide because they make it easy to compare options and book online. I also recommend independent local operators when I’ve experienced their tours myself. Cancellation policies vary, so check the conditions for your chosen tour.

Best Wine Tours from Florence: Quick Picks

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

OUR PICK: Best Small-Group Wine Tour from Florence

Duration: 5 hours
Type: Small-group Chianti wine tour (maximum 8 people)
Best for: Travelers who want a personal wine experience at small, sustainability-focused wineries

I recently joined this Afternoon in Tuscany with a Local Sommelier tour with Your Vino, and it’s now my top recommendation for wine tasting in Chianti. What makes it stand out is the combination of small family-run wineries, generous tastings, and a real focus on sustainable winemaking.

The experience starts in Florence, where you’ll board a van with a maximum of eight participants. Our guide, Sebastian, first took us to San Miniato al Monte, one of my favorite viewpoints in Florence, for a quick photo stop before heading into the beautiful Chianti countryside.

Our first winery was a family-owned estate of about 20 acres, divided between vineyards and olive groves with around 700 olive trees. When we arrived, we actually met the owner and his parents, who were busy harvesting olives! It was lovely to see the family going about their work rather than just arriving at a tasting room.

Here, we tasted four wines, including a rosé, a Canaiolo, a Chianti Classico, and a Chianti Classico Gran Selezione. Our favorite was the Gran Selezione, because apparently we have expensive taste!

The tasting came with a shared platter of local salami, cheese, and bread, plus some excellent olive oil produced right on the estate. The olive oil was a highlight for me!

Then we continued to the second winery, another relatively small producer tucked away in the Chianti hills. Like the first, it produces around 40,000 bottles a year, so this wasn’t one of those huge wineries set up for busloads of tourists.

At this second estate, we enjoyed six more wines, including Chardonnay, Chianti Classico, and two Super Tuscans. I particularly liked the variety of the tasting, which gave us the chance to compare different styles of Tuscan wine.

We also visited the cellar to see where the wines are stored and aged, learning more about the production process. Afterward, we had some time to enjoy the countryside views and take photos before returning to Florence.

Something else I really appreciated was how seriously both wineries take sustainability. At the first estate, they explained that they don’t use fertilizers at all, relying instead on natural farming methods, ground cover, and carefully selected sprays to protect their vines.

The second winery has even earned Diversity Ark certification, recognizing its efforts to protect biodiversity and preserve the local ecosystem. I love discovering producers who care about the land as much as the wine, and this made the experience particularly interesting to me.

Why this is the best tour

What sets this tour apart is the small group size and the opportunity to visit two working wineries with a strong commitment to sustainability. We tried ten wines in total, met the people behind them, and had plenty of time to ask questions. It’s a lovely way to experience Chianti without spending an entire day away from Florence.

Read what the reviews say:

“The winery choices were perfect, delicious wines, exquisite views and great people to interact with and learn about their craft.”

Jennifer Ashton – Google review

This tour includes round-trip transportation from Florence, a local sommelier guide, visits to two small wineries, wine tastings, and Tuscan snacks and olive oil tasting. ➥ BOOK IT HERE

If you’d prefer to spend a full day exploring Chianti, Your Vino also offers an 8-hour small-group wine tour visiting three family-run wineries, with a traditional Tuscan lunch and wine pairings. Groups are also limited to eight people. ➥ CHECK OUT THE FULL-DAY TOUR HERE

Best 4×4 Wine Safari from Florence

Duration: 7 to 9 hours
Type: Small-group wine tour
Best for: Travelers looking for a 4×4 countryside experience with wine tastings and a Tuscan meal

This Small-Group Wine Safari: Tuscany Wine Tasting Tour from Florence is my favorite alternative if you want a more adventurous countryside experience. You get wine tastings, beautiful views, and a 4×4 drive along scenic Tuscan roads without organizing transport or winery reservations yourself.

One important thing to know before booking: this tour page has a few different options. The shorter option visits one boutique winery plus a Tuscan Wine Club for a meal. I recommend the Full-Day Wine Safari if you want two winery visits, several tastings, 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 bus trip, as you’ll follow scenic countryside roads and off-road routes through vineyards, olive groves, and rural Tuscany.

You’ll visit family-run wineries in Chianti, where you’ll sample regional wines, taste olive oil and other local foods, and learn how wine is made and aged. You’ll also have plenty of opportunities to enjoy the countryside views.

The full-day itinerary also includes a stop at a Tuscan Wine Club for a 3-course meal, with regional dishes paired with local wine. It’s a proper sit-down meal rather than just a few snacks between tastings.

Between the winery stops and the Wine Club, you’ll travel along country roads through the Chianti hills. The 4×4 element is what makes this experience stand out from a typical wine tasting tour.

This is a great choice if you want an outing that focuses on wine but also feels like a countryside adventure. The tour can have up to 27 participants though, so it’s not as intimate as the eight-person top pick.

Check the booking option carefully. The full-day and shorter versions have different numbers of winery visits. The off-road sections can also be bumpy, and the supplier advises against this tour for pregnant travelers or people with back problems.

Pros

• Travel through Chianti in a customized 4×4 vehicle
• Full-day option combines two wineries, a Tuscan meal, and wine tastings
• Good choice for people who want a more adventurous countryside outing

Cons

• Group size can be up to 27 people
• Off-road driving may be uncomfortable if you have back problems
• Supplier says it cannot accommodate lactose intolerance and some other dietary requirements

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

The full-day option includes transportation by 4×4 vehicle, an English-speaking wine expert guide, visits to two wineries, wine tastings, olive oil and local food tastings, and a traditional Tuscan meal. ➥ BOOK IT HERE

Best-Value Chianti Wine Tour 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 Chianti Wineries Tour with Wine Tasting from Florence 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.

If you’re more interested in exploring Tuscan towns than wine tasting, check out my best Tuscany tours from Florence for more options.

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 in 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.

If you’d rather rent a car and explore the countryside at your own pace, my 7-day Tuscany itinerary can help you plan your route.

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 sightseeing day trip might be a better fit.

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.