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8 Best Tuscany Wine Tours from Florence

If you’re in Florence then you’re forbidden from leaving without taking a mega epic day trip to Tuscany.

I mean, not only is Tuscany SUPER close to Florence, but this region is home to rolling hills, medieval villages, incredible vineyards, and some of the best wine in Italy.

Now, sure, you can visit via train or hire a rental car in Tuscany. But, if you’re short on time – or just plan to drink like whoa – then book one of the best Tuscany wine tours from Florence instead.

Not only do these Tuscan wine tours from Florence make traveling a breeze, but they provide you with a stellar way of enjoying all of the area’s most epic highlights in a short amount of time.

Trust me, I have done tons of the best Chianti wine tours from Florence and 99.9% of them have been lovely. So much so that I’ve gone back and done even more wine tours.

So, if you love wine but want to quickly and easily see all that Tuscany has to offer then this post is for you.

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My #1 pick 🏆 for the best Tuscany wine tour from Florence is this small group wine-tasting tour. It’s well-priced, well-reviewed, includes delish wine 🍷, and isn’t HELLA long.

Best Tuscany Wine Tours from Florence

1. From Florence: Tuscany Wine & Food Tour with Guide

Aerial view of the vineyards in Tuscany.

⭐️ Rating: 4.9/5.0 (688 Reviews) Price: $161.70 per person Duration: 8 hours 📍Meeting Point: Piazzale Montelungo Operator: Prestige Rent – Tours in Italy Details: Read more on Get Your Guide Now!

Prepare for an epic day of fun during this Tuscany Wine and Food Tour with a guide.

See, this is one of the best Tuscany wine tours from Florence that will introduce you to three organic wineries where you can sample a wide variety of local wines.

So, start this small group tour with a scenic drive through the Tuscan countryside before learning all about wine-making at the very first vineyard you visit.

Explore the farm and tour the cellar before heading to a hilltop estate where you’ll meet a local wine expert before sitting down to lunch.

You’ll try delicious olive oil and amazing balsamic vinegar during your light meal before taking a walk through the idyllic village of Greve in Chianti.

“What a fantastic day! It was amazing being able to try 3 different wineries. Most were red wine (which I’m not a fan of, but actually very much enjoyed on this trip) but there were also a few white wines. Lunch was awesome. Personally, the trip was little long, so I would recommend doing the shorter trip (everyone started getting car sick to some degree with all of the hills). But, the tour guide did a great job and I would definitely recommend this activity.”

Matalin (read more reviews now)

Enjoy some free time in the main square before ending the tour at a historic family-owned villa.

You’ll take in stellar views of Florence and can explore one of the most gorgeous gardens in Tuscany before ending your Tuscany wine tour from Florence.

Get to visit three different wineriesA bit of a long day
Can enjoy a light lunch where you sample olive oil and balsamic vinegarSample mostly red wines
Amazing wineries that teach you all about local wineCan feel a bit salesy at times
Driver and guides (shout out to Leo) are amazing

2. From Florence: Small Group Wine Tasting Tour to Tuscany

A view of the green vineyards of Tuscany and the rolling hills of the region.

⭐️ Rating: 4.8/5.0 (1387 Reviews) Price: $96.39 per person Duration: 4.5 hours 📍Meeting Point: Piazzale Montelungo Operator: Prestige Rent – Tours in Italy Details: Read more on Get Your Guide Now!

If you’re looking for one of the best Tuscany wine tours from Florence that won’t take the entire day then book this Small Group Wine Tasting Tour to Tuscany.

Now, after departing from Florence in an AC-filled minibus, you and your group will make their way towards Chianti Classico.

Along the way, your English-speaking driver/guide offers in-depth commentary before visiting two amazing wine estates.

Enjoy three wines and fresh olive oil at the first place as you learn all about unique vinicultural practices.

“It was sensational. Fantastic guide, very good and comfortable transport. Short journey (45min) to the first winery and then the second is very close. Winery 1. Cheeses and breads with wonderful vinegars and oils + 4 wines (just the bottom of the glass). Winery 2. Cheeses, cold cuts and sausages, and bread + 5 wines (just the bottom of the glass). Possibility to buy wines, oils and vinegars on the tour. I thought the amount of wine was good, enough to make me neither sober nor drunk. I recommend going at the beginning of the trip, because if you make friends, they can be company for the next few days.”

Rodrigo (read more reviews now)

Continue to the second winery and sample a variety of wines and olive oils that are perfectly paired with local cheese, bruschetta, salami, and more. Seriously yummy food to say the least.

Yup, I loved this tour and thought that Raffaele and Alessio were both great. They shared a ton of great info and you got to try lots of great wines, olive oils, and balsamic vinegar.

It was a great way to get a taste of Tuscany without becoming totally exhausted by a massively long day trip.

Shorter day trip where you get to visit two different wine estatesWine purs can sometimes be small
Get to sample five great winesTour may not wait for anyone who is running late
Get to sample local sausage, cold cuts, cheese, bread, olive oil, and vinegarMusic in the vehicle can feel a bit liud
Very reasonable price compared to other tours

3. Florence: Chianti Wineries Tour with Food and Wine Tasting

girl friends toasting with wine glasses during a wine tasting in venice.

⭐️ Rating: 4.5/5.0 (4563 Reviews) Price: $53.18 per person Duration: 4.5 hours 📍Meeting Point: Piazzale Montelungo bus stop Operator: Ciaoflorence Tours & Travel Details: Read more on Get Your Guide Now!

During this most excellent Chianti Wineries Tour with Food and Wine Tasting, you’ll drive to the Chianti region and visit two different wineries.

At the first stop, you’ll embark on a guided tour of the vineyard and learn about what a “Chianti Classico” distinction requires before sampling four incredible wines during an on-site tasting.

Your expert guide will explain each of the wines you’re sampling, teach you how to properly taste each one, and even give you local bread, cheese, olive oil, and salami to enjoy.

“Excellent tour – learnt something about wine; but that’s not really the point – had an excellent guide in Nathan and loved all the wines which we were served. The best place for us was the smaller winery where the tastings were excellent. Would recommend and def come back.”

Neel (read more reviews now)

Next, stop at a scenic overlook so you can admire the Chanti Hills before learning about wine production at the second winery.

You’ll even go on a quick guided tour of the vineyards and then sit down to enjoy three unique wines before returning to Florence.

You sample a lot of different wines and they all taste greatCool explain the background of the wines a bit more
You will visit two wineries, one more modern and one more traditionalCan feel like a limited number of snacks for the entire group
Get free time after each tasting to explore the wineryGroups can be very large and have almost 40 people
Not wheelchair accesible

4. Florence: Pisa, Siena, San Gimignano, and Chianti Experience

A view of the leaning tower of pisa and the white church sitting next to it as people stand near the bottom taking photos. You can see this and more during one of the best Tuscany wine tours from Florence.

⭐️ Rating: 4.4/5.0 (2895 Reviews) Price: $69.46 per person Duration: 12 hours 📍Meeting Point: Sightseeing Experience Visitor Center Operator: Sightseeing Experience Details: Read more on Get Your Guide Now!

I love, love, LOVE this Pisa, Siena, San Gimignano, and Chianti Experience since it isn’t all about wine.

Yes, you’ll get to enjoy an amazing wine tasting. But, you’ll also get to see some of the top attractions in the region, making this one of the best Tuscany wine tours from Florence if you’re short on time.

So, your day will start with a lovely tour of Pisa. You’ll see the cathedral, the cemetery, the baptistery, and – DUH – the leaning tower before checking out a classic winery near San Gimignano.

Dig into an incredible Tuscan lunch and wine tasting before visiting the cobblestone streets, quaint squares, and local artisans of medieval San Gimignano.

“Barbara and Armando executed their roles admirably, ensuring seamless coordination throughout the tour. Navigating three major cities and historic sites was a pleasure, thanks to their competence. Barbara, our patient tour guide, adeptly managed the challenges posed by tardy and irresponsible attendees, displaying a commendable level of professionalism. Despite a few hiccups caused by irresponsible passengers, all individuals eventually boarded, and the return journey transpired without incident. The experience, albeit dramatic at times, was salvaged by Barbara’s unwavering professionalism. The driver’s exceptional skills contributed to a smooth and enjoyable ride. On the downside, the light lunch provided fell short of expectations. Regrettably, it resembled more of a simple snack with a sample wine tasting, and did not meet our culinary preferences. Nevertheless, the overall value derived from the expenditure was undeniably worthwhile.”

Sam (read more reviews now)

Afterward, stop to admire some panoramic views of Chianti before heading to Siena. Here, your guide will introduce you to Piazza del Campo and the cathedral.

You’ll then have free time to eat some panforte and shop for souvenirs before returning to Florence as the sun sets in the background.

So, all in all, this is one of the best Tuscan wine tours from Florence if you don’t feel like drinking wine all day but still want to see what this incredible region has to offer.

Get to see a lot of sights in a short timeLong day at 12 hours
Transportation included WiFiLunch could be better and is a bit small
Very well-organizedGroups can be big and have 40-50 people
The guides are very engaging and have a lot of great storiesTours can be conducted in two different languages

5. Tuscany by Vespa Full-Day Tour to Chianti Wine Region

Vintage red vespa in front of a green bush.

⭐️ Rating: 4.7/5.0 (132 Reviews) Price: $161.70 per person Duration: 6 hours 📍Meeting Point: Florencetown Booking Office Operator: Florencetown / Towns of Italy Details: Read more on Get Your Guide Now!

If you want to explore Tuscany in an entirely unique way – or just feel like channeling your inner Lizzie McGuire – then check out this Vespa Full Day Tour of the Chianti Region.

After all, you’ll start the day off with a quick pickup in a comfy, air-conditioned van that will take you to the beautiful, Chianti countryside.

Upon arrival, you’ll be briefed on how to use your 50cc original Piaggio Vespa safely before starting a magical ride through the scenic hills and charming country roads of Tuscany.

“An incredible day seeing the beautiful hills of the Chianti region outside of Florence. My husband drove the scooter and I got to take photos and experience all the magic of this wine country. Loved this trip!! Highly recommend. Tanya and Gracia were outstanding guides- friendly and knowledgeable.”

Kelly (read more reviews now)

You’ll cruise through enchanting medieval villages and stop at a villa from the 17th century to enjoy a traditional Tuscan meal.

You’ll even do a guided tour of the vineyard/cellars and take part in an iconic olive oil/wine tasting before heading back to Florence.

All in all, this is one of the best Chianti wine tours from Florence if you’re looking for a truly one-of-a-kind experience.

Pro Tip: I loved the fact that we got to drive through the town of Greve. We then got some nice sandwiches and 30 minutes of free time upon arrival.

We also got an excellent 3-course meal (apps, meat, cheese, and pasta) with wine.

Well-paced 6-hour tour with exceptional guides like AlexNot meant for people who have little or no experience riding Vespas
Only a 20-minute drive from Florence to the spot where you’ll ride the VespaNo sommelier to conduct the wine-tasting
Sandwiches and 3-course meal/wine tasting included
The tour is very well-organized

6. Florence Wine Tasting and Tuscan Lunch in a Vintage Fiat 500

⭐️ Rating: 4.8/5.0 (93 Reviews) Price: $161.16 per person Duration: 4 hours 📍Meeting Point: 500 Touring Club Operator: 500 Touring Club Details: Read more on Get Your Guide Now!

Stop what you’re doing and check out this mega epic wine-tasting and Tuscan lunch in a vintage Fiat 500.

You’ll start your day with a crash course (pun intended) on using the Fiat 500. You’ll then drive as part of a vibrant group from Florence to the Tuscan hills.

“The Florence wine tasting and Tuscan lunch in a vintage fiat500 tour was brilliant!! Alessandro was our tour guide & he helped make the experience so memorable. Alessandro was very professional but very easy going, knowledgeable & friendly. During the tour, we made mutiple stops to enjoy the most beautiful scenery, Where Alessandro told us stories/facts etc. During the wine tasting, we were welcomed into a Tuscan families home, where they had prepared meats, cheeses and breads for us to taste with the wines. Alessandro was very informative with the wine pairing. We met 2 fantastic couples on the tour, who made the tour even more fantastic & enjoyable for us as we all shared stories and laughed from start to finish. We 10/10 would recommend this tour and we would absolutely come back to do it all over again Alessandeo, thank you so much for an unforgettable experience!”

Michelle (read more reviews now)

Next, step inside a historic, 15th-century, Renaissance villa where the owners will give you a tour of the grounds and vineyards before descending into the wine cellar for a tasting of their award-winning vinos.

Afterward, dig into a light lunch and sample a variety of local olive oils that will expertly complement your meal.

Just be aware of the fact that you will have to pay a fuel surcharge of €15 for using the car.

This tour sticks to quiet country roadsFuel surcharge of €15 per car
Family villa so very personal experienceMust be an experienced manual driver to do this tour
Riding in the Fiat is a ton of funLunch can feel a bit light to some people
Wines are good and staff can quickly deal with any breakdowns

7. From Florence: Tuscany Day Trip with Lunch at Chianti Winery

Glasses of wine

⭐️ Rating: 4.8/5.0 (3043 Reviews) Price: $92.25 per person Duration: 12 hours 📍Meeting Point: Santa Maria Novella train station Operator: Walkabout Tours Details: Read more on Get Your Guide Now!

If you’re looking for one of the more traditional Tuscany wine tours from Florence then have a look at this Tuscany Day Trip with Lunch at Chianti Winery.

Sure, it’s not a super unusual tour. But, you’ll get to see all of the area’s major attractions in just twelve hours.

Therefore, try to get a good night’s sleep so that you can meet your group early at Florence Central train station.

You’ll then head to Siena where you’ll enjoy a guided tour of this medieval city before taking some free time to walk around.

In total, you’ll visit for around 90 minutes to admire the stunning Gothic and Romanesque architecture of the area (specifically the main cathedral) before grabbing lunch in the Tuscan Hills.

“This was the best thing I have done the whole time in Italy! The absolute best thing to do when I’m Florence, our guide Noemi was amazing and so great. The lunch at the winery in Chianti was delicious and going up Pisa was also worth the stairs. Definitely recommend this trip, it was raining all day and we still had a really great time. Would do it again in a heartbeat!!”

Marley (read more reviews now)

This lunch is optional but HIGHLY recommended since you’ll eat a homemade, organic meal paired with four regional wines – all while admiring sweeping views of the area.

Afterward, continue to San Gimignano. It’s a fabulous, UNESCO World Heritage site where you can take in epic panoramas and see tower homes from the Middle Ages.

Explore the town for an hour and a half before ending your day in Pisa. You’ll see the Leaning Tower and will walk through the Piazza dei Miracoli before making your way back to Florence.

Just choose between a small group or a private tour and let the fun begin during one of the best Tuscany wine tours from Florence.

Delicious lunch included with amazing viewsThe day can feel a bit long since this is a 12-hour tour
Excellent guides who are entertaining and share a lot of infoBy the time you arrive in Pisa, things can start to close
You can bring your luggage if you have a flight/train to catch after the tourFeels like you don’t get enough time in Siena
Entry to Leaning Tower of Pisa not included

8. Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

⭐️ Rating: 4.5/5.0 (1178 Reviews) Price: $72.71 per person Duration: 11 hours 📍Meeting Point: Varies Operator: CAF Tour & Travel Details: Read more on Get Your Guide Now!

Rounding out this list of the best Tuscany wine tours from Florence is this S. Gimignano, Siena, Chianti, and Wine Tasting Lunch.

During this epic experience, you’ll start off with a 70-minute scenic drive through Tuscany to San Gimignano.

You’ll then have around two hours to explore this ancient city on a hill before driving another 40 minutes to the Chianti Hills.

Upon arrival, relax at a local winery and sample three local wines, along with authentic balsamic vinegar.

“Just loved it all from start to finish just for me the walking was a bit much but that is because I hadn’t realised there would be quite so the history of the area and learning more about the wine of the area and it was a nice small number of people on the tour.”

Jayne (read more review now)

Afterward, dig into a delicious three-course lunch and get a taste of authentic Chianti cuisine.

Menu highlights include things like bruschetta, penne with meat ragout, and a homemade tart for dessert.

Finally, end the day with a one-hour guided tour of Siena that is followed by an optional tour of the Cathedral.

You’ll then enjoy some free time where you can check out the Basilica of San Domenico before going back to Florence.

Pros Cons
Very well-organized tourThe tour does require a fair amount of walking
Delicious meal with a great wine tastingTime in Siena can feel a bit short
Get to see stunning villages in the heart of TuscanyThe itinerary can change in the winter
Great way to see Tuscany in a short amount of time

My #1 pick 🏆 for the best Tuscany wine tour from Florence is this small group wine-tasting tour. It’s well-priced, well-reviewed, includes delish wine 🍷, and isn’t HELLA long.

Best Tuscany Wine Tours from Florence FAQ

1. Can You Take a Train from Tuscany to Florence?

Yes, you can take a train from Tuscany to Florence. That is because Livorno, Pisa, Siena, San Gimignano, and Lucca all have direct connections with Florence by train.

2. How Far is Tuscany from Florence?

Tuscany is very close to Florence and only about 9 kilometers away. Therefore, it could take you just twenty-five minutes to drive to Tuscany from Florence.

3. How to See Tuscany from Florence?

Some of the ways you could see Tuscany from Florence are by rental car, via one of the best Tuscany wine tours from Florence, or by train since two depart for Tuscany hourly.

One will take you to Siena directly while the other will take you to Empoli. Once in Empoli, you’ll have to change trains. However, one-way tickets for both trains usually cost just €6.80.

4. What to See in Tuscany in 3 Days?

With 3 days in Tuscany, you could spend your first day in Florence and see the Piazza Duomo, Giotto’s Bell Tower, and the Baptistery.

On day 2, make your way to Chianti and San Gimignano so that you can do some epic wine tastings and explore medieval architecture.

Finally, spend your third day in Siena where you can explore the Piazza del Campo, the Palazzo Comunale and Torre del Mangia, and the Duomo.

There you have it! That just about wraps up this guide to the best Tuscany wine tours from Florence.

Tell me, did your picks for the best Tuscan wine tours from Florence make the list? If not then let me know.

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