8 Best Tuscany Day Tours from Florence (Selected by a Local)

Florence is not only one of Italy’s most beautiful cities. It is also the perfect base for exploring Tuscany’s medieval towns, vineyards, and countryside. If you have at least three days in the area, I recommend spending two days in Florence and using the third to explore the Tuscan countryside.

I grew up in Bologna, just a short train ride from Florence, and I have visited Tuscany more times than I can count. Yet Siena’s medieval streets, San Gimignano’s towers, and the vineyards around Chianti never get old.

A tour makes sense if you do not want to rent a car or spend your day coordinating trains and buses. Some tours focus on famous towns, while others are designed around wine, food, or outdoor experiences.

To help you choose, I have selected the best Tuscany tours from Florence. They include classic sightseeing tours, wine experiences, a private day trip, a cooking class, and an e-bike ride.

➥ Why trust me? I’m Italian and have spent years traveling around Tuscany. I also have more than a decade of experience helping travelers plan trips to Italy. I carefully check the route, inclusions, group size, and practical details of every tour I recommend.

I usually book activities through Viator, GetYourGuide, and Walks. Most tours offer free cancellation until 24 hours before the experience, but always check the policy before booking.

Best Tuscany Tours from Florence: Quick Picks

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

OUR PICK: Best Tuscany Tour from Florence

Duration: 10 hours
Type: Shared group tour, maximum 25 people
Best for: A balanced day of sightseeing, food, and wine

This Siena and San Gimignano Small-Group Tour with Winery Lunch is my top pick because it offers a good balance of guided sightseeing, free time, food, and wine.

You’ll leave central Florence in the morning and travel to Siena for a guided walk through its historic center. The tour covers the city’s medieval streets and Piazza del Campo. Entry to Siena Cathedral is optional and costs extra, and it is not available on Sundays or during some celebrations.

The route then continues through the Tuscan countryside. You’ll pass Monteriggioni before stopping at a winery for a cellar visit, lunch, and tastings of regional red wines.

Your final stop is San Gimignano, where you’ll have around 1 hour and 15 minutes of free time. You can walk through the medieval center, admire its towers, and stop for gelato before returning to Florence.

Why this is the best tour

It visits two of Tuscany’s most beautiful towns without trying to squeeze too many places into one day. You get a proper guided visit in Siena, free time in San Gimignano, and a winery lunch that is already included in the price.

The maximum group size of 25 is also smaller than on many of the large coach tours. Vegetarian and gluten-free meals can usually be arranged if you notify the operator in advance.

Read what the reviews say:

“The winery lunch was delicious and handled dietary restrictions well. It was a good blend of structured tour and free time.”

Daniel_P – Read more reviews

This tour includes roundtrip transportation, an English-speaking tour leader and driver, a guided visit of Siena, free time in San Gimignano, and a winery lunch with wine. Siena Cathedral admission is not included. ➥ BOOK IT HERE

Siena, San Gimignano and Pisa Tours from Florence

Most Comprehensive: Siena, San Gimignano, Pisa and Winery Lunch

Duration: 12 hours
Type: Guided group tour
Best for: Travelers who want to see Tuscany’s major highlights in one day

This Tuscany Day Trip from Florence is the most comprehensive tour in this list. It visits Siena, San Gimignano, Pisa, and a countryside winery in one day.

The first stop is Siena, where a local guide leads you through the medieval center for about 1.5 hours. Depending on the option you book, the visit may also include entry to Siena Cathedral.

You’ll then spend around two hours at a family-run farmhouse and winery. The lunch option includes a Tuscan meal paired with four wines. Afterward, you’ll have about 1.5 hours to explore San Gimignano independently.

The final stop is Pisa, with roughly 1 hour and 15 minutes to see Piazza dei Miracoli and the Leaning Tower. Climbing the tower requires the correct ticket option, and children must be at least eight years old.

Pros

• Visits Siena, San Gimignano, Pisa, and a Tuscan winery
• Guided walking tour of Siena
• Excellent choice for travelers with limited time

Cons

• Long 12-hour day with a busy schedule
• Lunch, Siena Cathedral, and the Leaning Tower depend on the option selected
• The operator can accommodate vegetarians, but not gluten-free or other special diets

This tour includes roundtrip transportation, an English-speaking tour leader, a guided visit of Siena, and free time in San Gimignano and Pisa. Cathedral entry, lunch with wine, and Leaning Tower access depend on the option selected. ➥ BOOK IT HERE

If Siena is the main reason for your day trip, you can find more options in my guide to the best Siena tours from Florence.

Best Small-Group Option: Chianti, San Gimignano and Siena

Duration: 9 hours
Type: Small-group tour, maximum 14 people
Best for: Travelers who prefer a smaller group and a slower route

The Tuscany Day Trip from Florence with Chianti, San Gimignano, and Siena is limited to 14 people. It starts with a stop at Piazzale Michelangelo for views over Florence.

You’ll then travel to San Gimignano and have time to explore the medieval town independently. Afterward, the tour continues to a family-run Chianti winery for a cellar visit, lunch, and tastings of five wines.

The last stop is Siena. You’ll visit Piazza del Campo and see the exterior of Siena Cathedral, followed by time to explore on your own.

This tour is a good choice if group size matters more to you than having guided visits in every town. The tour leader accompanies the group throughout the day, but this does not include licensed city tours or entry to Siena Cathedral.

Pros

• Maximum group size of 14 people
• Winery lunch and five wine tastings included
• Vegetarian, pescatarian, and many allergy-related requests can be accommodated with advance notice

Cons

• No licensed guided walking tours inside the towns
• Siena Cathedral entry is not included
• More expensive than the larger coach tour

This tour includes roundtrip transportation, a tour leader, a professional driver, a winery visit, lunch, and five wine tastings. ➥ BOOK IT HERE

Tuscany Wine Safari from Florence

Duration: 7 to 9 hours
Type: Wine shared group tour
Best for: Travelers who want a wine-focused day in the countryside

This Small-Group Tuscany Wine Safari focuses on the wine estates and landscapes of Chianti. Instead of visiting Siena or San Gimignano, you’ll travel along country roads and through vineyard areas in a customized 4WD vehicle.

An English-speaking sommelier accompanies the group and explains the region’s wines and production methods. During the winery visits, you’ll explore historic estates and cellars before taking part in guided tastings.

Food is also an important part of the experience. The tour includes several wines, extra virgin olive oil, cheeses, cured meats, and a traditional Tuscan lunch or dinner. The meal is served at a countryside venue and paired with local wine.

The exact itinerary depends on the option you book. The full-day experience advertises visits to two family-owned wineries, while the shorter morning and afternoon options visit one boutique winery before lunch or dinner. Check the duration and departure time carefully when booking so you select the version you want.

The minimum age is 18. The off-road journey can also be bumpy, so it is not recommended during pregnancy or for travelers with serious back problems.

Pros

• Led by an English-speaking sommelier
• Several wine and local food tastings included
• Off-road route through vineyards and private estates
• Traditional Tuscan lunch or dinner included

Cons

• Does not visit Siena, San Gimignano, or other Tuscan towns
• The group can include up to 27 travelers
• The off-road drive can be bumpy
• Lactose-free and other alternative diets cannot be accommodated

This tour includes transportation by customized 4WD vehicle, an English-speaking sommelier, winery and cellar visits, several wine tastings, olive oil, cheese and cured-meat tastings, and a traditional Tuscan lunch or dinner. Hotel pickup and gratuities are not included. ➥ BOOK IT HERE

If wine tasting is your priority, check out my complete guide to the best wine tours from Florence. It includes more Chianti, Brunello, and private options.

Val d’Orcia Tour from Florence

Duration: 10.5 hours
Type: Small-group tour, maximum 8 people
Best for: Val d’Orcia landscapes, Brunello wine, and smaller villages

This Val d’Orcia tour takes you farther south to explore Montalcino, Pienza, and Montepulciano. It’s a great choice if you want to combine famous Tuscan wine, hilltop towns, and beautiful countryside in one day.

You’ll first visit a family-owned winery near Montalcino to learn about Brunello wine and taste different vintages. After a brief stop near the Fortress of Montalcino, you’ll continue to Pienza for a three-course lunch with wine and free time in the historic center.

The final stop is Montepulciano, where you’ll explore a historic underground cellar and enjoy another wine tasting with local foods. Town time can vary, so I would choose this tour mainly for its wine, food, and Val d’Orcia scenery.

Pros

• Maximum group size of eight people
• Two wine tastings and a high-quality lunch included
• Beautiful route through the Val d’Orcia countryside

Cons

• The driver is not a licensed tour guide
• Time inside the villages can be limited
• No hotel pickup in Florence

This tour includes transportation by premium minivan, two wine tastings, lunch, an English-speaking driver, a guided vineyard and cellar visit, an underground cellar tour in Montepulciano, and a food tasting. ➥ BOOK IT HERE

Private Tuscany Tour from Florence

Duration: 8 hours
Type: Private tour for up to 7 people
Best for: Couples, families, or groups who want private transportation

This Private Siena, San Gimignano, and Chianti Day Trip offers hotel or apartment pickup in central Florence and a private vehicle for your group.

You’ll first travel to Siena, where you can explore Piazza del Campo, Siena Cathedral, and the historic streets independently. The trip then follows the scenic Chianti road toward San Gimignano. You’ll have about two hours to explore San Gimignano before returning to Florence.

An optional winery lunch and tasting can be arranged during the day. The lunch costs around €50 to €70 per person and is paid directly at the winery. Adding it reduces the time available in Siena and San Gimignano. Your driver can offer local information, but this is not a privately guided walking tour.

Pros

• Private vehicle for up to seven people
• Pickup from central Florence hotels and apartments
• More comfortable and flexible than a large group tour

Cons

• The driver is not a licensed guide
• Lunch and wine tasting cost extra
• Adding the winery lunch reduces sightseeing time

This tour includes central Florence pickup and drop-off, a private luxury vehicle, air conditioning, bottled water, and an English-speaking driver. The winery lunch, wine tasting, admission tickets, and licensed guides are not included. ➥ BOOK IT HERE

Unique Tuscany Experiences from Florence

Best for Food Lovers: Pasta, Pesto and Tiramisù Cooking Class

Duration: 5 hours
Type: Farmhouse cooking class
Best for: Travelers who prefer a hands-on food experience

This Pasta and Pesto Class with Tiramisù replaces a traditional sightseeing day with a hands-on cooking experience in the Tuscan countryside.

You’ll meet in central Florence and, depending on the option selected, begin with a market visit. A minibus then takes you about 20 minutes outside the city to a farmhouse.

During the class, you’ll prepare a seasonal four-course meal. A typical menu can include bruschetta, pappardelle with sausage and tomato or ravioli with pesto, roast pork, and tiramisù. You’ll then sit down to eat everything with Tuscan wine.

This is a fun choice if you have already visited Tuscany’s main towns or want a shorter experience. However, the listing states that vegetarian, gluten-free, and other alternative diets cannot be accommodated.

Pros

• Hands-on cooking class at a Tuscan farmhouse
• Four-course meal and wine included
• Recipes are emailed after the class

Cons

• Does not visit Tuscany’s famous towns
• Cannot accommodate vegetarian, gluten-free, or other alternative diets
• Not suitable for travelers with limited mobility

This experience includes roundtrip transportation from central Florence, the optional market visit selected at booking, the cooking class, a four-course meal, wine, recipes, and a cooking diploma. Hotel pickup and gratuities are not included. ➥ BOOK IT HERE

You can also compare this countryside experience with the best cooking classes in Florence, including several options held outside the city.

Best Active Experience: Private Self-Guided E-Bike Ride

Duration: 4 to 7 hours
Type: Private self-guided experience
Best for: Confident cyclists who want to explore independently

This Private Self-Guided E-Bike Ride in Tuscany lets your group explore the hills outside Florence without following a guide.

You’ll collect your bike, helmet, and GPS route before riding for around 45 minutes toward Fiesole and San Domenico. You can stop for coffee and enjoy views over Florence before continuing into the countryside.

The route then takes you to a vineyard near the Arno River. You can stop for food and wine before cycling to Piazzale Michelangelo and returning to the bike shop.

Food, wine, and the vineyard stop are not included in the price. This experience is best for regular or semi-regular cyclists with moderate fitness. The route is self-guided, although roadside assistance is available.

Pros

• Private experience for your group
• Flexible duration and self-guided pace
• Bike, helmet, GPS route, and roadside assistance included

Cons

• No guide accompanies you
• Food and wine cost extra
• Requires confidence cycling on roads and hills

This experience includes an e-bike, helmet, GPS route, phone holder, and roadside assistance. A guide, food, wine, and hotel transfers are not included. ➥ BOOK IT HERE

You’ll find more city and countryside rides in my guide to the best bike tours in Florence.

Is It Worth Taking a Tuscany Tour from Florence?

Yes, especially if you only have one day and do not want to rent a car. Tuscany’s towns are spread across the region, and visiting several of them with public transportation can involve slow or awkward connections.

A tour handles the transportation and lets you combine places that would be difficult to visit independently in one day. Many options also include a winery lunch, guided sightseeing, or tastings that would require separate reservations.

The main trade-off is time. Tours that include three towns and a winery can feel rushed. If you want more time in each place, choose the top pick or the smaller Walks tour instead of the 12-hour comprehensive option.

If you have several days available and enjoy driving, an independent Tuscany road trip gives you more freedom. For most travelers staying in Florence, though, an organized day trip is the simplest way to see the countryside.

FAQ: Tuscany Tours from Florence

What is the best Tuscany tour from Florence?

My top pick is the Tuscany Small-Group Tour to Siena and San Gimignano with Winery Lunch. It combines two beautiful towns with a guided visit to Siena, free time in San Gimignano, and lunch with wine at a Tuscan winery.

Which Tuscany tour from Florence visits Siena, San Gimignano, and Pisa?

The Tuscany Day Trip to Siena, San Gimignano, and Pisa is the most comprehensive option. It also includes a winery visit, with lunch and some attraction tickets depending on the option selected.

What is the best Tuscany wine tour from Florence?

I recommend the Small-Group Wine Safari from Florence if wine is your main priority. The exact itinerary depends on the option selected, but it includes winery visits, guided tastings, local food, and a Tuscan meal.

Are private Tuscany tours from Florence worth it?

A private tour can be worth the extra cost if you are traveling with family or friends. The Private Siena, San Gimignano, and Chianti Day Trip includes pickup from your accommodation in central Florence and lets your group travel without sharing the vehicle with other guests.

How long are Tuscany tours from Florence?

Most full-day Tuscany tours from Florence last around 8 to 12 hours. Wine tours and special experiences can be shorter, while tours that combine several towns usually take most of the day.