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Florence To Siena Tours

Take a day trip from Florence to Siena, a UNESCO medieval gem and top destination in Tuscany.
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4,875 travellers from around the world love this
Slide 1 of 15, Person walking towards Siena Cathedral in Tuscany, Italy, surrounded by greenery.
Person walking towards Siena Cathedral in Tuscany, Italy, surrounded by greenery.
Siena Cathedral with tourists in the square, part of San Gimignano, Siena, Monteriggioni, Chianti day trip.
Piazza del Campo in Siena with Torre del Mangia, Tuscany.
Dirt road leading to a villa surrounded by cypress trees in Chianti, Tuscany.
Tour bus parked among cypress trees in Tuscany, Italy.
Tourists taking a selfie in front of a historic building in Siena, Italy.
Group enjoying wine tasting in Tuscany during Siena, San Gimignano, and Pisa tour.
Bottles of Tuscan wine on a wooden table, featuring Chianti and Vernaccia di San Gimignano.
San Gimignano skyline with medieval towers under a blue sky, Tuscany, Italy.
Horse race at Siena's Palio, Tuscany, with riders in colorful attire.
Leaning Tower of Pisa with Pisa Cathedral on the left during a walking tour.
Tourists walking through a vineyard with San Gimignano towers in the background, Tuscany.
Tourists boarding a bus for the Tuscany in a Day tour, visiting Siena, San Gimignano, and Pisa.
San Gimignano town square with medieval buildings and tourists exploring.
Person serving bruschetta during a Tuscany food tour.
11 hrs 30 mins - 13 hrs 45 mins
2 more
  • Discover the Tuscan experience with its lyrical landscapes and edgy world-class art, with a guide in the language of your choice!

  • Visit the walled hill city of Siena, known for its medieval appeal and Gothic appearance. Check out the Piazza del Campo, known famously to hold the Palio Horse Race every year.

  • Explore the World Heritage Site of San Gimignano, an eternally sought-after destination with its skyline of medieval towers.

  • Discover Pisa and its renowned charm with places like Piazza dei Miracoli, and the famous Leaning Tower.

  • Enjoy a delicious Tuscan lunch with a local wine-tasting tour amidst the rolling hills in the Chianti region.

More details
  • Discover the Tuscan experience with its lyrical landscapes and edgy world-class art, with a guide in the language of your choice!

  • Visit the walled hill city of Siena, known for its medieval appeal and Gothic appearance. Check out the Piazza del Campo, known famously to hold the Palio Horse Race every year.

  • Explore the World Heritage Site of San Gimignano, an eternally sought-after destination with its skyline of medieval towers.

  • Discover Pisa and its renowned charm with places like Piazza dei Miracoli, and the famous Leaning Tower.

  • Enjoy a delicious Tuscan lunch with a local wine-tasting tour amidst the rolling hills in the Chianti region.

from Original price€65
€58.50

10% off

Slide 1 of 7, Piazza del Campo in Siena with Torre del Mangia and Palazzo Pubblico.
Piazza del Campo in Siena with Torre del Mangia and Palazzo Pubblico.
Streets of San Gimignano with historic stone buildings and tourists exploring.
Vineyards and olive groves in Chianti region, Tuscany, Italy.
Hand holding a glass of rosé wine in a Chianti vineyard during an e-bike tour.
Wine barrels in a cellar during Chianti wine tasting tour from Florence.
Tour guide holding a sign in a Chianti village during a wine tour from Florence.
Bus interior with passengers traveling from Tromso to Skjervoy.
10 hrs 30 mins - 11 hrs 30 mins
1 more
  • Visit Siena, San Gimignano, and Chianti in one well-paced day trip from Florence.

  • Enjoy a winery visit in the Chianti countryside with 3 wine tastings included.

  • Get free time in both Siena and San Gimignano to explore at your own pace.

  • Upgrade to a guided walking tour of Siena for deeper insight into its history and landmarks.

  • Travel comfortably with round-trip transfers and a multilingual tour leader.

More details
  • Visit Siena, San Gimignano, and Chianti in one well-paced day trip from Florence.

  • Enjoy a winery visit in the Chianti countryside with 3 wine tastings included.

  • Get free time in both Siena and San Gimignano to explore at your own pace.

  • Upgrade to a guided walking tour of Siena for deeper insight into its history and landmarks.

  • Travel comfortably with round-trip transfers and a multilingual tour leader.

from
€65
Slide 1 of 13, Siena cityscape with historic buildings and lush greenery during Chianti Half Day Wine Tasting Tour.
Siena cityscape with historic buildings and lush greenery during Chianti Half Day Wine Tasting Tour.
Women posing playfully with the Leaning Tower of Pisa in Italy.
Pisa Cathedral and Baptistery with tourists exploring the square.
Stone buildings in a sunny Tuscan village square, part of the Highlights of Tuscany tour.
People dining at a long table during Pisa, Siena, and San Gimignano day trip.
Visitors at the steps of a historic church in San Gimignano, Italy.
Bus traveling through Chianti vineyards during Florence wine tour.
Wine bottles and Italian appetizers on a table during a Pisa, Siena, San Gimignano & Chianti day trip.
Tourists enjoying a wine tasting experience in Tuscany during a Pisa, Siena, and San Gimignano day trip.
Siena Cathedral facade with tourists during the day in Siena, Italy.
Siena Cathedral interior with striped columns and ornate vaulted ceiling.
Tourists inside Siena Cathedral admiring frescoes and architecture, Italy.
Tour guide speaking to tourists in a historic street during Pisa, Siena, and San Gimignano day trip.
11 hrs 30 mins - 12 hrs
2 more
  • Explore four of Tuscany’s most iconic destinations in one well-planned day trip from Florence.

  • Enjoy free time in Pisa, San Gimignano, and Siena to explore at your own pace.

  • Savor authentic Tuscan flavors with a winery visit, wine tastings, and a traditional local meal.

  • Upgrade your experience with guided tours of Siena and its cathedral or access to Pisa’s famous tower.

  • Travel comfortably with round-trip AC coach transfers and a multilingual tour leader throughout.

More details
  • Explore four of Tuscany’s most iconic destinations in one well-planned day trip from Florence.

  • Enjoy free time in Pisa, San Gimignano, and Siena to explore at your own pace.

  • Savor authentic Tuscan flavors with a winery visit, wine tastings, and a traditional local meal.

  • Upgrade your experience with guided tours of Siena and its cathedral or access to Pisa’s famous tower.

  • Travel comfortably with round-trip AC coach transfers and a multilingual tour leader throughout.

from
€67.15
Slide 1 of 9, Aerial view of San Gimignano with medieval towers and surrounding countryside.
Aerial view of San Gimignano with medieval towers and surrounding countryside.
Siena Cathedral with tourists in the square, part of San Gimignano, Siena, Monteriggioni, Chianti day trip.
Group walking through vineyard on Siena, San Gimignano, and Chianti day trip.
Visitors at the steps of a historic church in San Gimignano, Italy.
Wine being poured into a glass during a Chianti tasting on a Florence day trip.
Tourists taking a selfie in front of historic architecture in San Gimignano, Italy.
Aerial view of Monteriggioni's medieval walls and surrounding Tuscan landscape.
Aerial view of Chianti winery with vineyards and Tuscan landscape.
Passengers seated inside a tour bus traveling from Paris to Mont St. Michel's Abbey.
9 hrs - 11 hrs
2 more
  • Discover two of Tuscany’s most iconic hill towns in one relaxed day trip from Florence.

  • Enjoy free time in both Siena and San Gimignano to explore at your own pace.

  • Taste regional flavors with a winery visit, 3 wine tastings, and a traditional Tuscan meal.

  • Upgrade to a guided Siena tour with optional Cathedral access for a deeper cultural experience.

  • Travel comfortably with round-trip AC transport and a multilingual tour leader.

More details
  • Discover two of Tuscany’s most iconic hill towns in one relaxed day trip from Florence.

  • Enjoy free time in both Siena and San Gimignano to explore at your own pace.

  • Taste regional flavors with a winery visit, 3 wine tastings, and a traditional Tuscan meal.

  • Upgrade to a guided Siena tour with optional Cathedral access for a deeper cultural experience.

  • Travel comfortably with round-trip AC transport and a multilingual tour leader.

from
€79

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What our guests say

Pinelopi A

Greece
Group
Jul 2026
Although we lost half of the trip because we could not find the meeting point we managed to find our group and live the experience at sienna ! The girls at the meeting point were very polite and helped me book train tickets to find the other people of my group. Barbara was super guide and kind! Thanks also rachel from headout chat who gave me some credits for another trip. I am grateful.

From Florence: Tuscany, Siena, San Gimignano & Pisa Day Trip

Fabrizio T

Italy
Solo
Jun 2026

+4 more

An exciting experience. Highly recommended and impeccably organized from start to finish. One of the highlights was Sandro, our guide. Professional, empathetic, engaging, and tireless. You can tell he loves his job. Lucky him—and lucky are those who get to work with him. I’d also put Adele, the guide who welcomed us in Siena, on the same level. Professional, engaging, empathetic, and special. She makes you want to return to Siena tomorrow to discover the countless things this Tuscan gem has yet to reveal to a fly-by visitor—things that she, as a true Sienese, surely knows.

From Florence: Tuscany, Siena, San Gimignano & Pisa Day Trip

Christopher M

Couple
Jun 2026

+1 more

Enjoyed being taken to places with a really great driver. The bus guide was very good especially impressed with 3 languages skill set. The wine tasting venue was great and very entertaining. Sienna guided tour was excellent. Great guide. Would have happily sacrificed Pisa for longer at vineyard as this seemed a little rushed. It was over lunch we gelled as a group and made new friends. Wasn't so impressed with the amount of walking involved from bus to venue. It didn't help that the temperatures were 35°C. Overall an excellent tour.

From Florence: Pisa, Siena, San Gimignano & Chianti Day Trip with Wine Tasting & Lunch

Melissa A

Australia
Couple
Jun 2026
Beautiful stop spots rich in art and culture, especially Sienna... and the wine tasting was fantastic! Our guide John was great too.

From Florence: Pisa, Siena, San Gimignano & Chianti Day Trip with Wine Tasting & Lunch

Yang Z

China
Couple
Jun 2026

+6 more

Alex is an incredibly warm and friendly guide! We absolutely loved this day trip to Siena, San Gimignano, and Monteriggioni. For me, visiting the actual locations from Ezio Auditore’s story was a real pilgrimage. As for the €22 lunch, it was fine, but if you prefer more freedom, feel free to choose your own restaurant—just make sure to be on time for the meeting. Finally, if you have the chance to visit a winery in Chianti, you absolutely must try Firmina. It’s a truly interesting wine to drink!

From Florence: Siena, San Gimignano & Chianti Day Trip with Wine Tastings

Lisa S

Couple
Jul 2026
Samuel and Elvis were a very pleasant team. Samuel was always empathetic and friendly. He patiently answered every question and went out of his way to ensure the guests’ comfort. It was also very important to him that everyone received all the information in a timely manner. His fun facts about the places we visited were very entertaining. Thank you for the wonderful experience.

From Florence: Siena & San Gimignano Day Trip with Wine Tastings & Lunch

Nearby cities to explore

Your Florence to Siena day trip experience

Around 1.5 hours from Florence, Siena and the Tuscan countryside make an achievable, full but not overwhelming day trip. From Siena Cathedral's striped marble and fan-shaped Piazza del Campo to vineyard-dotted Tuscan hills, you capture medieval city life and countryside in one day. Guided coach tours, small-group minivans, and direct buses keep transport simple, letting you enjoy the views rather than planning details.

Overview

  • Distance from Florence: 75 km (47 mi) south to Siena via highway routes
  • Typical travel time: 1.5–2 hours each way by coach or bus
  • On-site visit duration: 6–8 hours across Siena and other included Tuscan stops
  • Budget category: Mid-range overall; group tours moderate, private options significantly higher per person
  • Best season: April–June and September–October, outside peak summer and winter low season
  • Meeting/drop-off point: Florence Santa Maria Novella area, mainly Piazzale Montelungo central coach terminal
  • Key attractions: Siena historic centre, Piazza del Campo, Siena Cathedral, San Gimignano, Chianti wineries

What to expect on a Florence to Siena day trip

Comfortable transfers

Depart from Florence by coach or minivan, traveling through rolling Tuscan countryside directly to Siena and surrounding towns.

Siena historic centre

Follow a guided walk through medieval lanes to Piazza del Campo and Siena Cathedral, with time for photos and coffee.

Palio stories and Gothic art

Hear explanations of Siena’s Palio horse race, contrade flags, and Gothic cathedral details that reveal the city-state’s history.

San Gimignano hilltop wandering

Explore San Gimignano’s tower-lined streets at your own pace, browsing shops, viewpoints, and gelato spots on the hilltop.

Winery tastings and Pisa add-ons

On select itineraries, visit a Chianti winery for tastings and countryside lunch, or stop in Pisa for Leaning Tower photos.

Things to know before booking your Day Trips from City A to City B

  • Total duration & timing: Florence–Siena day trips last 10–12 hours, with departures between 7:30am and 9:00am; earlier departures suit travelers wanting more Siena and daylight.
  • Transit & road conditions: Most tours use coaches or minivans, highway–hill journeys 75–90 minutes each way; if you’re motion-sensitive, choose front seats when booking.
  • Group size options: Large-coach tours often carry 40–50 guests, while minivan options cap near 8–25; choose smaller groups if you value quieter pacing and interaction.
  • Expert guided insight: Some tours provide live guided walks in Siena explaining Palio history; transport-only options offer just a tour escort, better for independent explorers.
  • Customizable add-ons: Variants may add San Gimignano, Pisa, Chianti lunches, wine tastings, or Siena Cathedral entry; choose combinations matching priorities for scenery or church visits.
  • Accessibility & mobility note: Siena has cobbled slopes and uneven streets; full-day itineraries involve walking, so limited-mobility travelers should favor private or DIY options instead.

Which Florence to Siena day trip is right for you

Siena & San Gimignano: Day Trip of Medieval Tuscany by Minivan

Small-group minivan tour combining Siena and San Gimignano, with guided walks and countryside views, ideal if you want medieval highlights without a crowded coach.

  • Duration: Full day (~10–11 hours)
  • Inclusions: Round-trip minivan, guided Siena and San Gimignano walks
  • Transfers: AC minivan from central Florence meeting point
  • Group size: Small group in minivan (approx. 8–25)
  • Food: Typically free time for meals; check inclusions
  • Best suited for: Travelers wanting small-group comfort and medieval highlights

Guided Tour of Seina with Lunch and Wine Tasting at Chianti

Focuses on Siena’s history plus a relaxed Chianti countryside lunch and wine tasting, best if you care more about Tuscan flavors than multiple town stops.

  • Duration: Full day (~9–10 hours)
  • Inclusions: Guided Siena tour, Chianti lunch, wine tasting
  • Transfers: AC coach or minivan from Florence
  • Group size: Medium group (coach or minivan format)
  • Food: Tuscan lunch and Chianti wine tasting included
  • Best suited for: Food and wine lovers wanting Siena context

Siena, S. Gimignano, Pisa: Round Trip by bus from Florence with Tour Escort

AC coach day trip to Siena, San Gimignano, and Pisa with a tour escort and plenty of free time instead of structured guided visits.

  • Duration: Full day (~11–12 hours)
  • Inclusions: AC coach, tour escort, free time in three towns
  • Transfers: AC coach from central Florence meeting point
  • Group size: Large group on AC coach
  • Food: Meals not included; free time for dining
  • Best suited for: Independent explorers wanting flexible time in multiple towns

Main stops on your Florence to Siena day trip

Siena Historic Center & Piazza del Campo

Walk Siena’s medieval streets into fan-shaped Piazza del Campo, the city’s spectacular main square and home of the Palio horse race. Follow your guide past palaces, fountains, and contrada flags, then enjoy a few precious moments to grab a coffee, people‑watch, and soak up the atmosphere.

  • Recommended duration: 1.5–2 hours
  • Included: Yes, all tours

Siena Cathedral (Duomo di Siena)

Admire the striped marble façade of Siena Cathedral, then step inside on tours that include entry to see its soaring columns, inlaid floor, and jewel-like Piccolomini Library. Your guide helps decode the symbolism and stories, turning a quick visit into a highlight of your Tuscan day.

  • Recommended duration: 45–60 minutes
  • Included: Yes, some tours

San Gimignano

Head up to hilltop San Gimignano, a perfectly preserved medieval town crowned with stone towers. Wander its cobbled lanes, browse small shops, and look out over vineyards rolling away in every direction. There’s usually time for a gelato stop and those postcard-worthy skyline photos.

  • Recommended duration: 1–1.5 hours
  • Included: Yes, some tours

Chianti Winery Lunch & Wine Tasting

Pause in the Chianti countryside for a relaxed farmhouse or winery lunch. Taste local reds and crisp whites, sample olive oil and simple Tuscan dishes, and learn the basics of wine production from your hosts. It’s a welcome chance to sit, chat, and really feel rural Tuscany.

  • Recommended duration: 1.5–2 hours
  • Included: Yes, some tours

Pisa & the Leaning Tower

On extended itineraries, finish your day in Pisa’s Piazza dei Miracoli, where the famous Leaning Tower tilts beside the cathedral and baptistery. Capture the classic “holding up the tower” photo, stroll the lawns, or, on select tours, climb the spiral staircase for sweeping sunset views.

  • Recommended duration: 1–1.5 hours
  • Included: Yes, some tours

Closing line:
Entry to these attractions is included in all or some tours, depending on the experience you choose.

Your Florence to Siena day trip itinerary

Morning
Depart Florence by air‑conditioned coach and settle in for a scenic ride through rolling Tuscan hills. Arrive in San Gimignano, where your guide leads you past stone towers and into the central piazza, with time to explore narrow lanes and grab a quick gelato.

Afternoon
Continue into the Chianti countryside for a farmhouse or winery lunch, savoring simple Tuscan dishes paired with local wines. After this relaxed break, drive on to Siena for a guided walk toward Piazza del Campo and the striped marble Cathedral.

Evening
Enjoy some free time to wander Siena’s medieval streets, sip a coffee, or pick up souvenirs before rejoining your group. Then board the coach for a comfortable ride back through the Tuscan hills, returning to Florence in the evening with your day complete.

Best time to visit Siena

Weather & Climate:

Spring (April–June) and early autumn (September–October) are temperate, ideal for long walking tours through Siena and Tuscan hill towns. July–August bring intense heat on exposed stone streets. November–March are cooler, wetter, with occasional fog.

Events & Seasonal Highlights:

The Palio di Siena horse races on July 2 and August 16 transform Piazza del Campo into a vast grandstand. Harvest and wine events in September and October highlight rural Tuscany; festive markets enliven Siena in December.

Crowd Dynamics & Peak Windows:

Tourist numbers peak in July–September, with extreme congestion on Palio days. April, May, and October see moderate crowds and good availability on Florence–Siena tours. November–March are quietest but some services run reduced schedules.

How to get from Florence to Siena

Guided round-trip transfers from Florence are the simplest way to reach Siena. You travel by air‑conditioned coach or minivan with a tour escort, often combining Siena with San Gimignano or Chianti. Central meeting points, pre-booked routes, and a guaranteed ride back to Florence remove guesswork around bus timetables and ZTL rules. This is the recommended option if you want transport, basic sightseeing, and light guiding all wrapped into one stress-free day.

Helpful Tips for a Florence to Siena Day Trip

  • Lock in your Florence meeting point: Piazzale Montelungo behind Santa Maria Novella gets chaotic with multiple tours, so save the pin and route beforehand.
  • Check if Duomo entry is included: Many Florence–Siena tours only show the Cathedral outside, so choose one explicitly listing Siena Cathedral tickets if interiors matter.
  • Prepare for Siena’s slopes: Steep, polished stone lanes around Piazza del Campo and the Duomo are surprisingly slick, so wear supportive, non-slip footwear.
  • Pack a cover-up for churches: Siena Cathedral expects covered shoulders and knees, so a scarf or cardigan prevents last-minute clothing hassles.
  • Carry small euro coins: Pay toilets on the road and in Siena, plus Gelateria Dondoli in San Gimignano, may not welcome large notes or cards.
  • Pace yourself at the Chianti lunch: The farmhouse meal often includes generous Chianti refills, so sip slowly if you want to enjoy Siena’s afternoon hills.
  • Choose your seat if you get carsick: Tuscany’s winding roads between Siena, Chianti and San Gimignano feel gentler in front seats of coach or minivan.
  • Don’t plan to be dropped in Siena: Florence–Siena tours are round-trip and usually forbid suitcases, so use buses or a private transfer for one-way travel.
  • Check Palio dates before booking: On 2 July and 16 August Siena packs out, and tours may reroute or shorten Piazza del Campo visits.
  • Plan ahead for bringing wine home: Winery stops sell bottles, but check airline baggage limits and space on the coach before buying multiple heavy souvenirs.

Frequently asked questions about day trips from Florence to Siena

  • Most day trips last about 10–12 hours. The drive is roughly 1–1.5 hours each way, with around 1.5–3 hours in Siena itself. The rest of the time is spent driving through the countryside and visiting extra stops like San Gimignano, Chianti wineries, or Pisa.

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