Florence isn’t just a breathtaking city—it’s also the perfect base for exploring the rolling hills, medieval towns, and world-class wineries that make Tuscany so special.
If you have at least three days in the area, I’d recommend spending two days in Florence and using the third to venture into the Tuscan countryside—trust me, it’s worth it.
Having grown up in Bologna, just 30 minutes away, I’ve taken plenty of trips through Tuscany, and it never gets old.
Whether it’s sipping Chianti at a family-run vineyard, getting lost in the narrow streets of San Gimignano, or standing in front of the Leaning Tower of Pisa wondering if it’s really that tilted, every visit offers something special.
In fact, I always recommend spending more time in the region(maybe on a Tuscany road trip?) but if you have limited time in Italy, I’ve got you.
To help you make the most of your trip, I’ve handpicked the best Tuscany tours from Florence, covering wine, history, scenic landscapes, and private experiences.
➥ Why should you trust me? Growing up in Bologna, just a short train ride from Florence, I’ve spent countless days exploring Tuscany—and I know exactly what makes a tour worth your time and money. With over a decade of experience in the travel industry, I carefully select tours that offer authentic, high-quality experiences, so you can book with confidence knowing you’re getting the best.
I personally use Viator, Get Your Guide, and Walks to book activities around the world. I especially recommend them for their fantastic cancellation policy. If your travel plans change, you can cancel most tours up to 24 hours in advance for a full refund.
OUR TOP PICK: Chianti, Siena and San Gimignano
If you want to experience the best of Tuscany in just one day on small-group, boutique tour, the Tuscany Day Trip from Florence with Chianti, Siena, and San Gimignano is the way to do it.
Your day starts in Florence, where you’ll hop into a comfortable, air-conditioned minibus and make a quick stop at Piazzale Michelangelo, hands down the best viewpoint in the city.
Then, it’s off to Siena, one of my favorite towns in Tuscany. The Siena Cathedral is absolutely stunning, and Piazza del Campo, the famous shell-shaped square where the Palio horse race happens twice a year, is even more impressive in person.
By midday, you’ll be more than ready to eat. You’ll head to a family-run vineyard in Chianti for a farm-to-table lunch with local ingredients—think fresh pasta, regional cheeses, and Tuscan olive oil.
And of course, you’ll tour the wine cellars and taste multiple wines produced on-site.
The last stop of the day is San Gimignano, a medieval town that looks straight out of a fairy tale. You’ll start with a guided walking tour, then have free time to explore. I recommend climbing the bell tower for the best panoramic views, but if you’re more into sweets than heights, this town is also home to one of the best gelaterias in Italy.
By the time you make your way back to Florence, you’ll be full, happy, and slightly buzzed from all the wine—which, in my opinion, is the perfect way to end your day in Tuscany.
➤ Why is this our top pick? It’s an incredible tour that combines culture, history, great food and wine, spectacular landscapes, and fun, all rolled into one. It offers free time to do your own thing, as well as guided visits in which you’ll learn about the region, and the small group guarantees a personalized experience.
Read what the reviews say:
“This was a fantastic tour, our best so far. The pace of the day was great with a perfect mix of guided tour and free time to explore Siena and San Gimignano. Our guide, Connie, was so knowledgeable, helpful, and organized. And the lunch and wine tasting were among our best meals. Our favorite day so far in Italy! Grazie mille!”
Monica – Read more reviews here
This tour includes: Roundtrip transportation, a guided walking tour in Siena and San Gimignano, lunch with wine tasting, and a guide. ➥ BOOK IT HERE
OUR 2nd PICK: The Most Comprehensive Tour to Tuscany from Florence
I usually only pick one top tour to recommend, but this time I couldn’t choose between the most comprehensive tour (ideal for those who have limited time) and the boutique tour to the countryside – so I picked both!
If you’re looking for a super-comprehensive day trip from Florence, the Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa, and Lunch at a Winery is the one. In just one day, you’ll visit three of Tuscany’s most iconic destinations—Siena, San Gimignano, and Pisa—with a delicious Chianti winery lunch in between.
After meeting your guide near the train station in Florence, your day starts with a guided tour of Siena, where you’ll admire its stunning medieval streets, visit the Duomo, and hear all about the famous Palio horse race in Piazza del Campo.
Then, you’ll head into the Chianti hills for a wine tasting and farm-to-table lunch at a family-run vineyard, where you’ll sip local wines while overlooking the countryside. This part is optional: if you’re on a budget, you can choose to skip it, but I recommend opting for the full tour for the ultimate Tuscan experience.
After lunch, it’s off to San Gimignano, a charming hilltop town famous for its medieval towers. You’ll have free time to wander its picturesque streets before heading to your final stop: Pisa.
Here, you’ll visit Piazza dei Miracoli to see the Leaning Tower, Duomo, and Baptistry, with the option to climb the tower for panoramic views (you can purchase your tickets in advance when you book the tour, which is suggested as you might not have a chance to buy them on the day of).
➤ Why is this a great tour to Tuscany from Florence? It includes visits to all of Tuscany’s major highlights, ensuring a comprehensive tour around the region-in just one day! Aside from getting to the best viewpoints and towns, you’ll sip regional wine, Tuscany’s gem product. Plus, the reviews are excellent.
Read what the reviews say:
“Our favorite day in Florence and maybe all of Italy. It is a long day but definitely worth being able to see the smaller towns. The winery was beautiful and the wine was delicious. We were able to ship wine home from the winery much cheaper than any of the stores we tried.”
Chris_W – Read more reviews here
This tour includes: Roundtrip transfers, a guided tour of Siena, entrance to the Cathedral, all visits, and lunch with wine tasting. ➥ BOOK IT HERE
Tuscany Wine Tours from Florence
I’ve written a whole post about the best wine tours from Florence. But I’ll save you time, here are the very best ones.
▶️ Check out this Wine Safaris: Off-Road Tuscany Wine Tours and Lunch. You’ll hop on a 4×4 vehicle and drive through the Chianti region as you learn about its landscapes and wine production from a very savvy guide.
The first stop will be at a family-run winery, where you’ll learn about Chianti wine and its making process as you tour the cellars. You’ll then enjoy a delicious wine tasting paired with cured meats and olive oil.
After your tasting, head to the property’s underground tunnels, which will lead you to an olive oil mill. It’s quite an adventure! Refuel with a 3-course meal at a Tuscan restaurant, paired with more Chianti wine, before your last stop: a historic villa.
You’ll walk around its impressive gardens and enjoy a final tasting of wines and cheeses on-site.
This tour includes: Roundtrip transportation, a guide, lunch, and food + wine tastings.➥ BOOK IT HERE
▶️ A great alternative is the Florence: Chianti Wineries Tour with Food and Wine Tasting. You’ll travel to the Chianti countryside with a professional guide, and visit two local wineries for a comprehensive visit.
You’ll have a chance to talk to the winemakers as you tour the vineyards and winery cellars, learning about the winemaking process, all the way from grape to wine. You’ll then be treated to tastings of up to 7 different wines, paired with cheeses, olive oil, and balsamic vinegar.
The tour lasts around 6 hours, and it includes roundtrip transfers from a meeting point in Florence.
This tour includes: Roundtrip transportation, winery tours, a guide, wine tastings with food pairings, and a stop at a viewpoint. ➥ BOOK IT HERE
An Essential Pisa Tour
How about joining a Pisa Day Tour with Leaning Tower of Pisa to discover one of the most renowned works of architecture? Pisa is one of the most iconic cities in Tuscany, mainly because of the world-renowned Leaning Tower.
You’ll enjoy a guided tour around Piazza dei Miracoli, where you’ll learn about the history and architectural facts of each monument, which include the Cathedral, the Baptistery, and of course, the Leaning Tower. Don’t miss out on the hilarious photo ops!
You’ll skip the lines to access the landmark and climb to the top for fantastic views of the square. Explore the Cathedral and Monumental Graveyard as well, before making use of your free time in Pisa.
This tour includes: Roundtrip transfers, a guided tour of Pisa, free time, and entrance fees to the Cathedral and the Leaning Tower. ➥ BOOK IT HERE
Looking for something different? Check out this other post about the best Pisa tours from Florence.
Tour To Siena and San Gimignano
▶️ Embark on a delightful Siena and San Gimignano: Small-Group Tour with Lunch from Florence for a memorable day filled with history, architecture, and great food. Your trip starts with a scenic drive to Siena, one of Tuscany’s most charming cities.
You’ll enjoy a guided walking tour through its winding cobblestone streets as you learn about its main landmarks and fascinating history.
Then, venture to San Gimignano, a hilltop town renowned for its medieval towers and historical atmosphere. You’ll have free time there before heading to Fattoria Lornano Winery, the next stop on the trip.
You’ll visit old cellars while learning about the wine, and relish a seasonal lunch of Tuscan delicacies paired with a great selection of wines.
This Tuscany bus tour from Florence includes: Roundtrip transportation, a guide, a tour of Siena, free time in both Siena and San Gimignano, and lunch with wine tastings. ➥ BOOK IT HERE
Again, for more options make sure to check out my other post about the best tours to Siena from Florence.
Tuscany Private Tours from Florence
▶️ Traveling with a group? Choose this Private Siena, San Gimignano, and Chianti Day Trip from Florence instead. You’ll travel comfortably in a private vehicle to Siena, where you’ll marvel at the clamshell-shaped Piazza del Campo and the majestic Cathedral.
Next up is a trip to the village of Monteriggioni, driving through the scenic Chianti hills. You’ll have free time to explore this enchanting town before visiting another Tuscan gem: San Gimignano.
Spend some time exploring it, and if you choose to include the option, you’ll then enjoy a tasty lunch with wine pairings at a local farm or winery
This will, however, reduce the time in Siena and San Gimignano and exclude Monteriggioni from the itinerary, so it’s up to you.
This tour includes: Hotel transfers, free time in all locations, bottled water, and an English-speaking driver. ➥ BOOK IT HERE
▶️ A good alternative is this Private Tuscany Tour: Siena, Pisa, and San Gimignano from Florence, which accommodates groups of up to eight.
You’ll have a full day to wander around the cities of Siena, Pisa, and San Gimignano at your own pace. Take in their striking architecture, soak up the history and artistry of each city, and admire the views.
The itinerary is flexible and adapts to your interests, so you can choose how long (or little) to spend in each destination. You can even add a trip to a local winery to sip on Vernaccia wine and enjoy a hearty meal.
This tour includes: Hotel pick-up and drop-off, free time in Siena, San Gimignano, and Pisa, bottled water, and a flexible itinerary. ➥ BOOK IT HERE
Cooking Class at a Tuscan Farmhouse
▶️ Unleash your inner chef in this Cooking Class and Lunch at a Tuscan Farmhouse with Local Market Tour from Florence. You’ll first visit a bustling market, where you’ll follow a local chef as they pick the freshest ingredients for your class.
Then, head to a beautiful farmhouse, and put into practice the tips and techniques a lead chef will teach you to craft a mouthwatering 4-course lunch. You’ll be let in the secrets of Italian cuisine as you whip up bruschetta, handmade tagliatelle, a meat course, and tiramisu. An authentic feast!
At the end of the class, indulge in your creations paired with Tuscan wine.
This tour includes: Roundtrip transfers, a market visit, a cooking class, lunch with wine, a cooking diploma, and all the recipes. ➥ BOOK IT HERE
Tuscany Bike Tour from Florence
▶️ Want to try a bike tour? This E-Bike Florence Tuscany Self-Guided Ride with Vineyard Visit covers the region’s prime attractions: scenery and wine.
You’ll ride through the Tuscan countryside and scale the picturesque hills effortlessly, as the e-bike will do the work for you. A GPS device will guide you to Fiesole, where you can visit a vineyard for Chianti-style wine and Tuscan treats.
The ride also includes a stop at Piazzale Michelangelo, which offers incredible views of Florence.
There’s no guide, so you’ll be free to roam at your own pace, getting your dose of wine, views, and adventure—Tuscany style!
This Tuscany bike tour from Florence includes: E-bike and helmet rental, GPS route, and a phone holder. ➥ BOOK IT HERE
