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    Florence Duomo ComplexAttraction in Florence, Italy

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  • Explore Montepulciano
  • Places to see
  • Things to do
  • Top sights
  • Attraction types
  • Outside Montepulciano

Piazza Grande, Montepulciano

Fattoria Svetoni, Montepulciano

Day trips

UNESCO sites

Viewing points

Nearby destinations

Florence tours

Siena tours

San Gimignano tours

Monteriggioni tours

Scandicci tours

Montalcino 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
  • Interests
  • Traveler type
  • Outside Montepulciano

Wine tasting & winery tours

Cooking classes

Pasta tasting & cooking classes

Factory & workshop tours

Cheese & charcuterie tastings

Olive oil tours & tastings

Bike tours

Horse riding

Scooters & motorcycles

Explore more things to do in Montepulciano

Culture & history

Outdoor activities

Nature & adventure

Explore more things to do in Montepulciano

Wheelchair accessible

Activities for couples

Family-friendly activities

Explore more things to do in Montepulciano

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 Montalcino

Explore more things to do in Montepulciano

From Siena: Tuscany Hills Wine Tour

4.148148 out of 5 stars
4.1
4.148148 out of 5 stars
324 reviews
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From Siena: Tuscany Hills Wine Tour
4.148148 out of 5 stars
4.1
4.148148 out of 5 stars
324 reviews
Likely to sell out

Taste the flavors of Tuscany on a daily tour of Pienza and Montepulciano. Cross rolling hills full of vineyards, and visit two wineries to sample local wines paired with snacks.

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 609 minutes
Check availability to see starting times
Live tour guide
Portuguese, Chinese, Spanish, English, Italian

Highlighted reviews from other travelers

P
Peter – New Zealand

The mixture of two winery visits and tastings, along with two beautiful towns and the scenery.

C
Christina – United States

Our guide- Marta- was excellent. The tour was gorgeous. We loved stopping in all the towns and seeing the sights. A day we won’t forget. Definitely worth it!!

Select participants and date

Participants

Itinerary

  • Timeline stop icon

    Starting location:

    Stazione FS di Siena

  • Bus/coach

    (1 hour)

  • Timeline stop icon

    Break time, Visit, Wine, Free time, Wine tasting, Local snacks (1 hour)

  • Transfer

    (70 minutes)

  • Timeline stop icon

    Pienza

    Break time, Photo stop, Visit, Lunch, Free time, Shopping, Sightseeing, Self-guided tour, Scenic views on the way (80 minutes)

  • Transfer

    (30 minutes)

  • Timeline stop icon

    Montepulciano

    Break time, Photo stop, Visit, Wine, Free time, Wine tasting, Shopping, Walk, Local snacks (105 minutes)

  • Bus/coach

    (15 minutes)

  • Timeline stop icon

    Break time, Photo stop, Visit, Wine, Free time, Wine tasting, Shopping, Sightseeing, Local snacks (1 hour)

  • Bus/coach

    (1 hour)

  • Arrive back at:

    Stazione FS di Siena

Main stop

For reference only. Itineraries are subject to change.

Highlights

  • Treat your taste buds to Tuscan wines paired with snacks
  • Explore Pienza and Montepulciano in the historical region of Val d'Orcia
  • Drive across the rolling hills and vineyards of Tuscany
  • Learn about wine making traditions from a guide in Monteriggioni, Chianti
  • Admire medieval castles and historic hillside towers

Full description

Experience the Tuscany Wine & Hills Tour from Siena, where you'll savor renowned wines like Chianti and Nobile di Montepulciano. Spend a day immersed in culture and wine as you explore stunning Tuscan destinations, including Pienza, and Montepulciano.

Start your day by meeting our team, where you'll start your full-day journey exploring the region’s highlights.

The adventure begins in the charming medieval village of Monteriggioni, where you'll join the other group and head over to the first canteen. Let the rolling hills of Chianti beckon you as you dive into the region's rich winemaking heritage. Visit a winery where you'll not only sample world-class wines but also learn about the craft of producing extra virgin olive oil—a blend of ancient olive varieties that embodies the essence of Tuscany. In the first cellar, you'll taste three different wines, gaining a deeper appreciation for each of their unique flavors and textures. Complement your tasting with a selection of home-produced olive oil and traditional Tuscan bread. Our knowledgeable guides will enrich your experience with insights into Tuscany's deep-rooted history, art, and rural culture.

Continue your journey into the scenic Val d'Orcia, stopping first in Pienza, a town where architectural beauty meets breathtaking landscapes. Wander through lanes with evocative names and enjoy panoramic views that have inspired countless artists and poets. Take some free time to explore the town on your own and savor a leisurely lunch.

Your tour then takes you to Montepulciano, where the grandeur of Renaissance architecture and the elegance of historic churches will enchant you. Delight in the traditional Nobile di Montepulciano wine as you explore the city and capture its stunning views.

The adventure continues with a visit to a second winery, where you’ll taste more locally produced wines, including the renowned Nobile di Montepulciano, paired with traditional snacks. Finally, relax and enjoy the scenic drive back to Siena, bringing your Tuscan journey to a close.

Includes

  • Transportation by air-conditioned bus or minivan
  • Multilingual escorts
  • Chianti and Nobile di Montepulciano wine tasting with snacks
  • Free time in Montepulciano and Pienza
  • Hotel pickup and drop-off
  • Lunch
  • Tips

Not suitable for

  • People with mobility impairments
  • Wheelchair users

Meeting point

Stazione di Siena - Ferrovia

Open in Google Maps

Important information

Know before you go

  • Customers should be able to climb and descend stairs.
  • The tour is confirmed only when the minimum number of people is reached
  • Customers must be able to climb and descend stairs. Please note that a moderate amount of walking is involved and this tour is not wheelchair accessible.
  • Please note that the Chinese and Portuguese options require a minimum of 4 participants. In case the minimum is not reached, the tour is guaranteed to be conducted in English.
Likely to sell out

From $148 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

4.1 /5

based on 324 reviews

Review summary

  • Guide
    4.3/5
  • Transportation
    4.4/5
  • Value for money
    4/5

Customer photos

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P
Peter – New ZealandMay 13, 2025 – Verified booking
The mixture of two winery visits and tastings, along with two beautiful towns and the scenery.

Response from provider

May 13, 2025

Dear Customer, Thank you for sharing your feedback with us! We're so glad to hear you enjoyed the mix of winery visits and tastings, as well as the beautiful towns and stunning scenery. It sounds like a truly memorable experience! We hope to welcome you on another tour soon. Best regards, My tour in Italy.

C
Christina – United StatesMay 7, 2025 – Verified booking
Our guide- Marta- was excellent. The tour was gorgeous. We loved stopping in all the towns and seeing the sights. A day we won’t forget. Definitely worth it!!

Response from provider

May 7, 2025

Dear customer, Thank you for sharing your feedback with us! We're so happy to hear you had a great time on the tour and that Marta made it even more special. It means a lot to know the day was unforgettable for you that’s exactly what we hope for! Hope to see you again soon on another adventure 😊 Best regards, My Tour In iTaly.

M
Michele – ItalyOctober 31, 2024 – Verified booking
The trip was very informative and enjoyable. Our driver Vincenzo was very knowledgeable and gave us historical and geographical information. We had enough time at the 2 wineries to take a tour and do tastings. Additionally we had enough time to eat and browse shops at the 2 towns we visited. Vincenzo was a great host and we really enjoyed our day.

Product ID: 60232

Activity provider:My Tour in Italy
  • Italy
  • Tuscany
  • Things to do in Montepulciano
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  • Vecchia Cantina di Montepulciano

Top Attractions in Montepulciano

  • 1Piazza Grande, Montepulciano
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Experiences in Montepulciano

  • 1Montepulciano Wine tasting & winery tours
  • 2Montepulciano Cooking classes
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