Siena and San Gimignano Day trip from Florence Tickets at Piazzale Montelungo

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From Florence: Siena, San Gimignano & Chianti Day Trip with Lunch & Curated Countryside Sips

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4.1· 842 reviews

Summarised reviews

Rated 4.1 out of 5, this Tuscany day trip earns consistent praise for knowledgeable, approachable guides and the beauty of the towns and countryside visited. Travellers highlight the rich history and scenic landscapes, though some note the lack of onboard facilities and occasional pacing issues during the wine tasting.

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Siena and San Gimignano Day Trip from Florence

This full-day tour takes you through three of Tuscany's most celebrated destinations, combining medieval history with countryside flavours. You'll explore the Gothic splendour of Siena, savour wines in the Chianti hills, and discover the tower-studded skyline of San Gimignano, all with comfortable transport and a three-course lunch included.

Your journey begins in Siena, where you'll wander the winding medieval streets leading to Piazza del Campo, one of Europe's most beautiful squares. With a local guide, you'll visit landmarks like the Basilica of San Domenico and Siena Cathedral, marvelling at its intricate marble facade and the artistic treasures within, including the vibrant frescoes of the Piccolomini Library.

The route continues through Chianti's rolling hills to a family-run winery, where a three-course lunch featuring local Tuscan specialities awaits. You'll sample regional wines, including the famous Chianti, and taste sweet vin santo while learning about traditional production methods against panoramic vineyard views. The final stop is San Gimignano, known as medieval Manhattan for its impressive towers, where you'll have free time to stroll cobblestone streets and capture the skyline against the Tuscan horizon.

What is Included

  • Round-trip transport from Florence in air-conditioned coach
  • Local guide for Siena exploration
  • Three-course lunch at a Chianti winery
  • Wine tasting including Chianti and vin santo
  • Free time in San Gimignano
  • Multilingual tour staff assistance
  • Additional stop at Monteriggioni (April to October)

Good to Know

The tour departs from Piazzale Montelungo and runs as a full-day experience. Arrive at least 15 minutes before departure for check-in. You'll need comfortable shoes for walking on uneven terrain and cobblestone streets, plus a valid photo ID for age verification at wine tastings.

Dress modestly for church visits in Siena. Wine tasting is reserved for adults aged 18 and over, though children are welcome when accompanied by an adult. The tour is not accessible for wheelchairs or strollers due to the terrain in these historic towns.

Vegetarian meal options are generally available at the winery lunch, but inform staff at booking or before the meal. The itinerary order may vary according to seasonal factors or local events to ensure the best possible experience. For more Florence day trips, consider the Pisa and Leaning Tower day trip or explore more of the region with a Florence Uffizi Gallery tour.

Why you'll love it

  • 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.

What's included

  • Round-trip AC coach transfers from Florence Onboard Wi-Fi access Multilingual tour leader Free time in Siena & San Gimignano Winery visit with 3 wine tastings Traditional Tuscan lunch Siena guided tour (as per option selected) Siena Cathedral guided tour (as per option selected)

Good to know

Opening hours
Tue10:00-19:00
Know before you go
  • Wear comfortable walking shoes as the tour covers varied terrain

  • Wine tasting is only for guests aged 18 and above

  • Order of visits may vary as per local conditions

  • Modest attire is required to enter religious sites like Siena Cathedral

  • Bring a valid ID for age verification and entry

Visitor guidelines
  • Please arrive at least 15 minutes before departure for check-in

  • Maintain respectful behavior at all locations, especially churches

  • Alcoholic beverages served only to adults 18 and over

  • Follow instructions from staff and guides for safety and comfort

Cancellation policy

Free cancellation

Frequently asked

Is this tour suitable for children?

Children are welcome but must be accompanied by an adult. Wine tasting is for guests aged 18 and above.

Do I need to bring anything?

Bring comfortable shoes, a valid photo ID for age checks and dress modestly for church visits.

Can I join if I use a wheelchair or stroller?

The tour is not accessible for wheelchairs or strollers due to uneven terrain.

Is lunch included?

Yes, a three-course lunch featuring local Tuscan specialties and wines is included at the winery.

Are there vegetarian meal options available?

Vegetarian options are generally available; inform the staff at booking or before lunch.

Where you'll be

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