Florence isn’t just about Renaissance art and historic landmarks—it’s also the gateway to some of Italy’s best food and wines. Tuscany, after all, is practically synonymous with rolling vineyards, charming hilltop towns, and the world-famous Chianti.
One of the best things about Florence is how easy it is to escape into the countryside for a day of wine tasting, something that should be on your Florence itinerary.
I was born and raised in Bologna, merely an hour north of Florence, and I have visited countless times throughout the years.
Not only would I claim to know the city almost as much as my own, but I’ve also explored the Tuscan countryside extensively and I really enjoy wine tasting in the region (although I can’t claim to be an expert by any means!)
As a local, I highly recommend you take a trip to the wineries of Tuscany. Learn everything about the process of winemaking, indulge in delicious tastings, and see jaw-dropping landscapes, all in one day.
The reason I suggest you join a wine tour is that it takes off the pressure of choosing a designated driver. Besides, the company will handle the reservations and find the best wineries for you to visit. In this article, I’ve compiled the very best wine tours from Florence for you to check out.
➥ Why should you trust my picks? Besides being a native of the region, who’s been to Tuscany a great number of times, I have over 10 years of experience curating tours in Italy. I have hand-picked only top-rated, good-value activities to ensure you have a memorable time.
I usually use and recommend Viator and Get Your Guide for booking tours around the world. Not only do they offer high-quality tours, but both platforms also have a great cancellation policy. If you need to change your plans, you can cancel most tours up to 24 hours in advance for a full refund.
Are you in a rush? These are the top tours:
| THE BEST TOUR | Wine Safari: Off-Road Tuscany Wine Tour and Lunch from Florence |
| TUSCANY TOUR WITH WINE | San Gimignano, Siena, and Chianti Wine Tour |
| PRIVATE TOUR | Private Tuscany Wine Tour Experience from Florence |
| WINE + COOKING CLASS | Pasta Making Class & Wine Tasting in a Tuscan Castle |
| E-BIKE WINE TOUR | Tuscany E-Bike Tour from Florence to Chianti |
OUR PICK: The BEST Wine Tour from Florence
The Wine Safari: Off-Road Tuscany Wine Tour and Lunch from Florence has been our top pick for years, and I often get emails from travelers saying that this wine tour was the highlight of their trip.
This full-day Chianti tour takes you on a 4×4 truck bus, the perfect vehicle for exploring the winding roads and hills of the Tuscan countryside. After meeting your knowledgeable guide in Florence, you’ll travel through the scenic landscapes of the countryside.
Your first stop is a wine estate owned by an important Florentine family. Explore its cellars and the olive mill through underground tunnels, and visit the processing facility while learning how wine is made. You’ll then get to taste three wines and two olive oils paired with cured meat.
Then, head to a Tuscan winery restaurant where you’ll get to enjoy a scrumptious 3-course meal and more wine with sweeping views of the vineyards. Fresh pasta and Chianti wine are to be expected!
Your last stop of the day is a private historic villa that only allows for visits with select tours. The garden of the villa is breathtaking, and the inside is art, and you’ll get to visit the villa on a guided tour before sitting down for a final tasting of 3 wines paired with cheeses.
➤ Why is this the best tour? For starters, it has over 3 THOUSAND 5-star reviews. The tour is very generous with the wine tastings (9 in total), taking you to three different locations to taste the local product, plus a 3-course delicious meal.
That also means you’ll have the chance to witness the scope of wineries available in the region. You’ll visit an established location that also produces olive oil, a local restaurant, and a smaller vineyard.
People rave about the lunch with insane countryside views, as well as the tasting in the historic villa. Plus, the 4X4 bus is such a fun vehicle!
It’s not just me saying it! 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: Roundtrip transportation, a guide, 9 wine tastings, and food tastings + lunch. ➥ BOOK IT HERE
Other Great Wine Tours To Consider
▶️ This Small-Group Wine Tasting Experience in the Tuscan Countryside takes you to the famed Chianti region. The tour will take you to 2 top-rated wineries, where you’ll explore the cellars and learn about the traditional techniques of winemaking.
In each of them you’ll be treated to tastings of regional wine, paired with fresh cheeses, olive oil, and bruschetta. The tour only lasts 4 hours, allowing you to make other plans for the afternoon.
This tour includes: Transportation, a guide, winery tours, and all tastings. ➥ BOOK IT HERE
▶️ The Florence: Small-Group Tuscany Wine & Oil Tour with typical Tuscan Meal is a guided experience. It’s led by an expert sommelier, who will take you to 2 different wineries in Tuscany, renowned for their red wines.
Sip 6 varietals after a comprehensive introduction to wine-making, and stop for lunch at a traditional restaurant. Relish regional specialties before heading to an olive oil mill for a guided visit.
This tour includes: Transportation, a guide, all visits, and tastings. ➥ BOOK IT HERE
Tuscany Tours from Florence with Wine Tasting
▶️ Explore the Tuscan Countryside with this San Gimignano, Siena, and Chianti Wine Tour from Florence. This full-day excursion allows you to delve into the wonders of the region as you explore cities, hilltop towns, and vineyards.
You’ll have a guided tour and free time in Siena, followed by a scenic ride among the Chianti hills on your way to a winery. Discover the behind the scenes of the wine making process, and enjoy tastings of local wines.
The tour continues to Colle di Val d’Elsa and San Gimignano, where you’ll have plenty of time to explore at your leisure.
This tour includes: Transfers, a guide, all visits, and wine tasting. ➥ BOOK IT HERE
▶️ The Tuscany Day Trip with Lunch at Chianti winery from Florence is a phenomenal excursion. It takes you to the city of Siena, where you’ll enjoy a comprehensive walking tour. Access the main cathedral, and explore the other monuments before heading to San Gimignano.
You’ll have free time to wander around its narrow, medieval streets and check out its impressive towers. A trip to Pisa, home to the famous Leaning Tower, is also included.
Finally, relish delicious Tuscan fare with wine tastings at a local winery. You can choose between a private or small-group trip for your utter comfort.
This tour includes: Transportation, a guide, entrance fees, lunch, and wine tasting. ➥ BOOK IT HERE
Limited Time? A Half-Day Wine Tour
If you can’t spare a whole day to go wine tasting, book this Chianti Wineries Tour with Food and Wine Tasting from Florence. You’ll head to the heart of Tuscany, and visit two local vineyards where you’ll delve into the process of making Chianti wine.
Take in the landscapes of rolling hills and vines, and sample several wines paired with cheeses, olive oil, and balsamic vinegar.
Throughout the trip, your guide will introduce you to the history and culture of the region.
This tour includes: Transportation, a guide, vineyard visits, and tastings. ➥ BOOK IT HERE
Private Wine Tours
Looking for a private tour to stay away from the crowds? No problem! In my opinion, these are the best options to make the trip with your group.
▶️ The Private Tuscany Wine Tour Experience from Florence accommodates groups of up to 8 people. You’ll be picked at your hotel, and travel to the countryside for a full day of gorgeous scenery and wine.
Guided by a sommelier, you’ll visit three different states to sample top-rated wines and olive oil. At a family-run winery, indulge in a full Tuscan lunch paired with more wine. You’ll be touring wine cellars and vineyards, and learn all about wine-making, from grape to bottle.
The itinerary is flexible, so you can customize it to suit your preferences.
This tour includes: Hotel pick-up and drop-off, a guide, wine tasting, and lunch. ➥ BOOK IT HERE
▶️ Traveling with your friends or family? Taste the Best of Tuscan Wines: Montalcino and Montepulciano is a perfect tour for red wine lovers.
It takes you to the medieval town of Montalcino, where you’ll have a scrumptious lunch and sample the famous Brunello di Montalcino wine.
The next destination is Montepulciano, birthplace of the Nobile di Montepulciano red wine. You’ll visit a winery for delicious tastings, and hear about the local history and winemaking culture from your guide.
It’s a personalized and very immersive experience for groups of up to 8.
This tour includes: Hotel pick-up and drop-off, a guide, and live commentary. ➥ BOOK IT HERE
▶️ This Private Full-Day Siena, San Gimignano, and Chianti from Florence is the perfect introduction to the region.
You’ll get to visit the iconic towns of Siena, San Gimignano, Monteriggioni, and Chianti all in one day. Your private guide will provide fascinating facts about the region and each location.
Learn about the making of wine from professionals, and indulge in a homemade 4-course lunch paired with different wines.
This Tuscany tour from Florence includes: Transfers, a guide/driver, free time, water, and optional lunch and wine. ➥ BOOK IT HERE
Half Day Chianti Wine Tour + Cooking Class
The Small-Group Pasta Making Class Wine Tasting in a Tuscan Castle is a spectacular wine tour that takes place in the dreamiest of locations.
You’ll head to a 900-year-old castle in Tuscany to learn all the secrets of the most beloved Italian dish. Enjoy a hands-on pasta-making class, and then relish your creations, followed by a delicious wine-tasting session led by an expert.
You can choose between a morning or afternoon tour.
This tour includes: A professional guide, a cooking class, lunch, and wine tasting. ➥ BOOK IT HERE
Tuscan Wine Experience by Vintage Fiat 500
The Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Wine Experience offers an experience like no other. You’ll drive your own 1960s vehicle among the Tuscan hills with a stop at a spectacular 15th-century villa.
There, enjoy a tour around the wine estate, cellars, and vineyards, and sample several wines and local bites. You’ll have time to explore the grounds at your leisure after lunch.
This tour includes: A Fiat-500 rental, a guide, a winery tour, lunch, and wine tastings. ➥ BOOK IT HERE
Tuscany Tour by Vespa with Wine Tasting
Check out this Small-Group Tuscany by Vespa to hop on the classic Italian bike and make your way into Chianti territory. Your local guide will lead the way to two different wineries, which you’ll tour as you learn about their workings and wine production.
Savor a Tuscan lunch at a farmhouse, paired with tastings of wine and olive oil, before driving back to Florence. You can choose between a morning or afternoon departure, and a single or double scooter.
The tour operates on a small-group basis to ensure safety and an intimate ambiance.
This tour includes: Vespa and helmet rental, a tour of the wineries, lunch, olive oil, and wine tasting. ➥ BOOK IT HERE
Tour by E-Bike with Winery Visit
▶️ Another great way to explore the Tuscan countryside is with the Tuscany E-Bike Tour from Florence to Chianti with lunch and tastings. It will give you a chance to ride your bike among the hills, vineyards, and olive groves without having to put any effort!
You’ll first stop at Piazzale Michelangelo, which offers the most astounding views of the city. Then, make your way to two wineries for delicious olive oil and wine tastings. Cap off the trip with a traditional Tuscan lunch paired with a glass of wine.
This tour includes: Bike rental, a guide, water, winery visits, wine tastings, and lunch. ➥ BOOK IT HERE
Interested in other foodie experiences in Florence? I mean, there’s never such a thing as too much when it comes to food in Italy! Check out my other posts about the best food tours in Florence and the top Florence cooking classes.
