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  • Explore Montalcino
  • Places to see
  • Things to do
  • Top sights
  • Outside Montalcino

Corte Pavone Winery

Fortezza di Montalcino

Paradiso di Cacuci

Temple of Brunello

Montepulciano Government Palace

Nearby destinations

Florence tours

Siena tours

San Gimignano tours

Monteriggioni tours

Montepulciano tours

Scandicci tours

Nearby sights

Florence Duomo ComplexAttraction in Florence, Italy

Ponte VecchioAttraction in Florence, Italy

Piazza della SignoriaAttraction in Florence, Italy

Uffizi GalleryAttraction in Florence, Italy

Accademia GalleryAttraction in Florence, Italy

Porta del ParadisoAttraction in Florence, Italy

  • Top experiences
  • Outside Montalcino

Wine tasting & winery tours

Fine dining experiences

Bus & minivan tours

Balloon tours

Cooking classes

Bike tours

Explore more things to do in Montalcino

Things to do in Florence

Things to do in Siena

Things to do in San Gimignano

Things to do in Monteriggioni

Things to do in Montepulciano

Explore more things to do in Montalcino

Siena: San Gimignano, Chianti & Montalcino Small-Group Tour

4.6 out of 5 stars
4.6
199 reviews
Activity provider:
My Luxury Drive
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Siena: San Gimignano, Chianti & Montalcino Small-Group Tour
4.6 out of 5 stars
4.6
199 reviews

Spend a day in the Tuscan countryside and discover the charms of medieval San Gimignano, Chianti, and Montalcino. Enjoy a wine tasting in a prestigious Chianti winery. Join an optional lunch.

About this activity

Free cancellation
Cancel up to 24 hours in advance for a full refund
Reserve now & pay later
Keep your travel plans flexible — book your spot and pay nothing today.
Duration 11 hours
Check availability to see starting times
Live tour guide
Spanish, English, Italian

Highlighted reviews from other travelers

5
5 out of 5 stars
B
Bon – Hong Kong

Excellent tour with a small group. The visit to the winery was a real highlight, highly recommended to those that want an intimate experience.

5
5 out of 5 stars
A
Ankit – United Kingdom

Fabio, our tour guide was very nice. He showed us and told us history quite nicely. Wine Tasting events were really enjoyable. I think if someone wants to experience Cianti Winery’s alongwith couple of towns, this is a good day trip.

Select participants and date

Participants

Itinerary

  • Starting location:

    Via Giuseppe Garibaldi, 72

  • Van

    (45 minutes)

  • San Gimignano

    Break time, Photo stop, Visit, Free time, Shopping, Sightseeing, Walk, Self-guided tour, Sunrise (2 hours)

  • Van

    (1 hour)

  • Winery

    Break time, Photo stop, Visit, Wine, Lunch, Guided tour, Free time, Wine tasting, Shopping (2 hours)

  • Van

    (1 hour)

  • Winery

    Break time, Photo stop, Visit, Wine, Guided tour, Free time, Wine tasting, Shopping, Food tasting (1 hour)

  • Van

    (10 minutes)

  • Montalcino

    Break time, Photo stop, Visit, Free time, Shopping, Sightseeing, Walk, Self-guided tour, Scenic views on the way (1.5 hours)

  • Van

    (1 hour)

  • Arrive back at:

    Via Giuseppe Garibaldi, 72

Main stop

For reference only. Itineraries are subject to change.

Highlights

  • Marvel at the walled medieval town of San Gimignano
  • Explore the Chianti region; enjoy a wine tasting and optional typical lunch
  • Taste world-renowned Brunello of Montalcino at a wine cellar
  • Visit the UNESCO World Heritage Site of Val d'Orcia
  • Visit Montalcino city and enjoy a stroll around its beautiful stronghold

Full description

The first part of your full-day tour begins with a visit to the walled medieval town of San Gimignano, the City of Fine Towers. Armed with helpful information from your tour escort you’ll have free time to explore the town’s historical center and browse its artisan shops.
Visit San Gimignano, the birthplace of Vernaccia, a white wine produced exclusively in the area. The wine is noted for its high quality and for being the first Italian DOCG wine. Afterwards, stop at a winery for an optional lunch of salami, cheese, and other local products, accompanied by Chianti tasting. 
Discover Val d’Orcia, another Tuscan jewel and a UNESCO World Heritage Site. Continue on to Montalcino, perched on a hill overlooking 1,500 hectares of Brunello vineyards that have contributed to the area’s international reputation.
Finally, enter a local wine cellar, where you’ll have a chance to taste the renowned Brunello of Montalcino, rated among the finest Italian DOCG wines.

Includes

  • Travel by air-conditioned minivan
  • Bilingual tour escort
  • Visit to San Gimignano (with free time)
  • Wine tasting at a farm in the Chianti region
  • Visit to Montalcino and its fortress (with a brief shopping stop)
  • Wine tasting at a renowned winery in Montalcino
  • Samples of typical Tuscan snacks
  • Opportunity to buy wine from the winery at special prices (shipping available to most countries)
  • Typical lunch (optional)
  • Tips

Not suitable for

  • Wheelchair users

Meeting point

Meet the staff of in front of Hotel Minerva, in Via Giuseppe Garibaldi 72, 53100, SI

Open in Google Maps

Important information

Know before you go

  • Customers must be able to climb and descend stairs.
  • This is a small-group tour with a maximum of 8 people in the minivan
  • Please note that pickup and drop-off is excluded from the price but can be required for accommodations located less than 10 km from the center of Siena for an additional fee.
  • The tour requires a minimum of 4 participants in total. If the participants are 2 or less, the supplier can suggest an alternative date or shift you on another tour. In this case no refund will be made. Otherwise, if the cancellation happens before 24 hours the full refund will be made. In case the tour doesn't take place for logistical reasons for the supplier side, the customer can request a refund through Get your Guide platform.

From $162 per person

Reserve now & pay later to book your spot and pay nothing today
Reserve now & pay later to book your spot and pay nothing today

Customer reviews

Overall rating

4.6 /5
4.6 out of 5 stars

based on 199 reviews

Review summary

  • Guide
    4.7/5
  • Transportation
    4.6/5
  • Value for money
    4.5/5

Customer photos

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5
5 out of 5 stars
B
Bon – Hong KongApril 29, 2025 – Verified booking
Excellent tour with a small group. The visit to the winery was a real highlight, highly recommended to those that want an intimate experience.
5
5 out of 5 stars
A
Ankit – United KingdomApril 21, 2025 – Verified booking
Fabio, our tour guide was very nice. He showed us and told us history quite nicely. Wine Tasting events were really enjoyable. I think if someone wants to experience Cianti Winery’s alongwith couple of towns, this is a good day trip.
5
5 out of 5 stars
J
Joanne – United StatesOctober 20, 2024 – Verified booking
Enjoyed all the sights. Could have spent more time in Pienza

Product ID: 44381

Activity provider:
My Luxury Drive
  • Italy
  • Tuscany
  • Things to do in Montalcino
  • Tours in Montalcino
  • Fortezza di Montalcino

Top Attractions in Montalcino

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