6 Best Siena Tours from Florence (by an Italian)

Planning a day trip from Florence to Siena? These Siena tours from Florence take care of the transportation, with options that also visit San Gimignano, stop for a winery lunch, or continue to Pisa. The tricky part is choosing how much to fit into one day!

I recently revisited Siena and found it much busier than I remembered, especially around the main sights. My advice is to check how much time you’ll actually spend in the city. You want a chance to enjoy its medieval streets and spectacular cathedral without constantly watching the clock.

Below, I’ve selected six tours for different kinds of days: guided sightseeing, smaller groups, a Pisa combination, dinner in Chianti, a budget option, and private transportation. Some include meals and guided walks; others give you more freedom with free time in the city.

I’ll explain how each day unfolds, what’s included, and which one I’d choose for different travel styles. To plan your time in the city around this day trip, see my 2 or 3 days in Florence itinerary.

➥ Why trust me? I’m Italian, from Bologna, and have spent more than 10 years helping travelers plan their trips to Italy. I’ve explored Siena myself and compared these tours by their itineraries, time in town, group sizes, and inclusions.

I usually book tours through Viator, GetYourGuide, or Walks. Check the inclusions and cancellation policy for your chosen tour and booking option before reserving.

Best Siena Tours from Florence: Quick Picks

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

OUR PICK: Siena and San Gimignano Tour with Winery Lunch

Duration: 10 hours
Type: Guided group tour, up to 25 guests
Best for: A guided introduction to Siena with a countryside lunch

After my most recent visit, I’d choose a tour that gives Siena a proper morning. That’s what draws me to this Siena and San Gimignano Tour with Winery Lunch: you get help understanding the city, then time to follow your own curiosity.

From Florence, you’ll head straight to Siena for a guided walk through its medieval streets. Explore the shell-shaped Piazza del Campo, hear about the Palio horse race, and admire the Torre del Mangia and the cathedral’s elaborate facade.

You’ll spend roughly 2.5 to 3 hours in Siena, including free time. After the walk, browse the shops or explore more on your own.

You can also pay €15 extra for a guided cathedral visit during this time. This add-on doesn’t run on Sundays or during religious celebrations, but I highly recommend it if you can! The cathedral is incredible.

Next, drive through the countryside for lunch and wine at a family-owned estate. Sit down to cured meats, local cheeses, pasta, and dessert, paired with 3–4 of the estate’s wines. A countryside meal is a lovely way to break up the sightseeing!

The final stop is San Gimignano. After a short introduction from your guide, you’ll have free time to explore its lanes and medieval squares, browse the shops, or grab a gelato before returning to Florence.

Why this is the best tour

I like the balance here: you get the history behind Siena’s streets, time to enjoy them on your own, and a countryside meal. It’s my pick for travelers who want Siena to be a substantial part of the day, with San Gimignano as the second town.

Read what the reviews say:

“Well paced with good mix of guided tour and free time. Beautiful winery complex for lunch with informative tour. Highly recommend”

Cynthia_W, October 2026 · Read more reviews

This tour includes roundtrip transportation from Florence, a guide, a guided Siena walk, free time in both towns, and a winery lunch with wine. Cathedral entry and its guided visit are optional extras. ➥ BOOK IT HERE

Siena, San Gimignano and Pisa Day Trip from Florence

Duration: 12 hours
Type: Guided group tour
Best for: Seeing Siena, San Gimignano, and Pisa in one day

The Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery is the most ambitious itinerary on this list, and begins with a guided tour of Siena. You’ll walk through its medieval streets to Piazza del Campo, learning about the Palio horse race held in this famous square.

Choose an option with Siena Cathedral entry to explore the Duomo’s art-filled interior, too, which is amazing. After the guided visit, you’ll have free time to browse the shops, stop for coffee, or wander through more of Siena’s historic center.

Next comes a farmhouse lunch with four wine tastings at a Chianti estate, if you select the lunch package. Then you’ll have free time in San Gimignano before continuing to Pisa’s Piazza dei Miracoli.

Climbing the Leaning Tower requires the ticket upgrade. This 12-hour trip suits travelers who want a guided introduction to Siena while fitting two more Tuscan towns into the same day. Expect a busy schedule with several bus journeys.

Pros

• Visit three famous Tuscan destinations
• Local guide for the Siena walking tour
• Lunch, cathedral, and tower-ticket options available

Cons

• A long day with several transfers
• Less flexibility at each stop
• Meals and attraction tickets depend on the selected package

This tour includes roundtrip transportation, an English-speaking tour guide, a guided Siena walk, and free time. Winery lunch, wine tastings, Siena Cathedral admission, and Leaning Tower tickets depend on the option booked. ➥ BOOK IT HERE

Small-Group Siena Tours from Florence

Siena and San Gimignano with Winery Lunch

Duration: 9 hours
Type: Small-group trip, up to 14 guests
Best for: Travelers who want a smaller group and independent exploring

This Tuscany Day Trip from Florence with Chianti, Siena and San Gimignano keeps the group to 14 guests. After a photo stop at Piazzale Michelangelo, you’ll head to San Gimignano for time to explore its medieval streets on your own.

A family-run Chianti winery hosts lunch with five wine tastings, then you’ll continue to Siena. The itinerary lists around two hours there, with free time to see Piazza del Campo and admire the cathedral’s exterior. Interior admission is extra.

A tour leader accompanies the trip, but town visits are based around free time. Choose this for a smaller group and a winery meal. Groups above eight may travel in two minivans, with the guide splitting time between vehicles.

Pros

• Maximum of 14 guests
• Winery lunch and five wine tastings included
• Free time in both medieval towns

Cons

• No dedicated guided city walk listed
• Siena Cathedral admission is extra
• The guide may divide time between two minivans

This tour includes roundtrip transportation, a driver and English-speaking tour leader, the viewpoint stop, free time in both towns, and winery lunch with five wine tastings. ➥ BOOK IT HERE

Siena and San Gimignano with Dinner in Chianti

Duration: 9 hours
Type: Shared guided tour
Best for: Combining sightseeing with a Tuscan winery dinner

The Siena and San Gimignano Tour with Dinner in a Boutique Winery starts with a guided walk through Siena. You’ll learn about Piazza del Campo and the city’s historic districts.

After free time among San Gimignano’s towers, head into Chianti for a Tuscan dinner with wine tasting. The winery visit includes its cellars. Outdoor dining depends on the weather, so book for the food and setting rather than a guaranteed sunset table.

Select the dinner option when booking. The same page also offers a longer Grand Tour with Pisa and lunch, which follows a different schedule.

Pros

• Guided sightseeing in Siena
• Winery dinner, wine tasting, and cellar visit
• Maximum of 20 guests

Cons

• A late return may not suit travelers with evening plans
• Outdoor dining depends on the weather
• Cathedral admission in Siena is not listed as included

This tour includes roundtrip transportation, a driver/tour leader, a guided Siena walk, a local tasting, free time in San Gimignano, and a winery visit with dinner and wine tasting when you select the dinner option. ➥ BOOK IT HERE

A Budget-Friendly Siena and San Gimignano Tour from Florence

Duration: 9 hours
Type: Bus trip with a tour leader
Best for: Independent exploring without a winery stop

If you’d rather spend the day exploring towns, this Day Trip with Free Time in San Gimignano and Siena keeps things simple. A bus takes you from Florence to San Gimignano, then Siena, with no winery stop along the way.

The itinerary allows around 2.5 hours of free time in each town. You decide how to use them, whether that means wandering the streets, visiting an attraction, or taking a lunch break. A tour leader and GPS audio guide are included.

The lower starting cost comes with fewer extras: meals, attraction tickets, and guided town visits are excluded. It’s a good fit if you’re happy planning your own sightseeing but want the transportation between stops taken care of.

Pros

• No time set aside for a winery visit
• Around 2.5 hours in each town
• Roundtrip transport and a tour leader included

Cons

• Meals and attraction tickets cost extra
• No guided walking tours included
• Fixed departure times limit how long you can stay

This tour includes roundtrip bus transportation from Florence, a tour leader, a GPS audio guide, and free time in San Gimignano and Siena. Food, attraction tickets, and guided town visits are excluded. ➥ BOOK IT HERE

Private Siena Tour from Florence

Duration: 8 hours
Type: Private driver service
Best for: Hotel pickup and independent sightseeing

Prefer your own vehicle? This Private Tuscany Tour from Florence includes hotel pickup and a private driver. Visit Siena and San Gimignano, then travel through the Chianti countryside.

Your driver provides commentary on board, while sightseeing in the towns is independent. Discuss your itinerary preferences with the operator when booking.

Wine tasting in the Chianti region is optional. You can arrange it yourself or ask the operator to organize it for you. Lunch is extra.

Choose this for privacy and convenience; book a guided city tour instead if detailed sightseeing commentary matters most.

Pros

• Private vehicle for your party
• Hotel pickup and drop-off
• Itinerary preferences can be discussed

Cons

• Independent sightseeing in the towns
• Lunch costs extra
• Wine tasting depends on the option

This tour includes private transportation, hotel pickup and drop-off, a driver, and onboard commentary. Wine tasting depends on your booking option. ➥ BOOK IT HERE

Is It Worth Taking a Siena Tour from Florence?

In my opinion, Siena deserves more than a day trip. I’d recommend staying longer if your itinerary allows it. There’s plenty to explore beyond the main sights, and it’s worth leaving time to wander.

But if one day is all you have, a tour makes the transportation much easier. Getting to Siena independently takes some planning, and the train station is quite far from the central attractions. Having the journey organized helps you make the most of your time.

A day tour is also ideal if you want to combine Siena with San Gimignano or a countryside winery.

I’d choose based on how much of the day you want to spend in Siena. A guided walk helps you understand the city, while free time lets you explore at your own pace. Just remember that every extra town or winery means less time in Siena itself.

Staying longer? Have a look at my guide to the best wine tours and tastings from Siena, including countryside trips and experiences in the city.

Siena Tours from Florence FAQs

Is Siena worth a day trip from Florence?

Yes. Piazza del Campo, the medieval streets, and Siena Cathedral make it a rewarding day trip. I’d leave room for wandering as well as the main sights, rather than trying to fit every attraction into a short stop.

How much time do these tours spend in Siena?

The time in Siena is much shorter than the total tour duration. Our top pick plans roughly 2.5 to 3 hours there, including guiding and free time. Other itineraries vary, so check the stop length as well as the overall schedule.

Do Siena tours include cathedral entry?

Not always. Some Siena, San Gimignano, and Pisa packages include cathedral entry, while other tours offer it as an extra or only visit the exterior. Check your exact booking option. Religious services can also affect access.

Can I visit Siena and San Gimignano without a winery stop?

Yes. The free-time day trip visits both towns without a winery stop. Transport and a tour leader are included, while you arrange your own meals, tickets, and sightseeing.

Can you visit Siena and other Tuscan towns on the same tour?

Yes. Several tours combine Siena with San Gimignano, and some also visit Pisa. If you’re still deciding which places to include, compare the routes in my guide to the best Tuscany tours from Florence.

How long are Siena tours from Florence?

The tours in this guide last around 8 to 12 hours, including transportation. The Pisa combination is the longest. Allow some breathing room afterward, especially if you’re making dinner reservations or catching a train.