Siena, Cortona, Montepulciano & Val D'Orcia in a Small Group Tour

4.9 (122 reviews)
12h
From
€171.00
per person
Popular experience Free cancellation Instant confirmation
See Available Dates !
No payment now — check real-time availability first
Lowest Price Guarantee
Duration
12 hours
Rating
4.9/5 (122)
Confirmation
Instant
Cancellation
Free up to 24h
Explore in the comfort of a 8 seat van the most beautiful Tuscan towns made famous through films together with a passionate local driving guide. Enjoy lunch overlooking the rolling hills of Montepulciano while tasting famous wine.

Is this experience for you?

You love authentic local food and flavors
You enjoy discovering cities on foot
You appreciate wine culture and local traditions
You're looking for a unique experience in Florence

Tour Highlights

Explore in the comfort of a 8 seat van the most beautiful Tuscan towns made famous through films together with a pass...
Enjoy lunch overlooking the rolling hills of Montepulciano while tasting famous wine.
Explore the locations made famous by Michelle Pfieffer in "A Midsummer night's dream" and Ralph Fienes in " The Engli...
Spot the iconic rolling hills of Tuscany from " Letters to Juliet" and enjoy a taste of the local lifestyle by sampli...

Full Description

Explore in the comfort of a 8 seat van the most beautiful Tuscan towns made famous through films together with a passionate local driving guide. Enjoy lunch overlooking the rolling hills of Montepulciano while tasting famous wine.

Wander the winding streets of Cortona walked by Diane Lane in "Under the Tuscan sun", watch out for the vampires of the Twilight saga " New Moon" in Montapulciano and taste the famous Noble of Montepulciano wine. Explore the locations made famous by Michelle Pfieffer in "A Midsummer night's dream" and Ralph Fienes in " The English patient". Spot the iconic rolling hills of Tuscany from " Letters to Juliet" and enjoy a taste of the local lifestyle by sampling fine local wine, cheese and other products from the region.
€171.00
per person • Reserve your spot
See Available Dates
You\'ll see available dates and times on the official booking page — no obligation
Best Price
100% Guarantee
24/7 Support
Dedicated assistance
Secure Payment
Protected transaction
Book Now, Pay Later
Reserve your spot free

Tour Photos

What's Included

Included

  • Alcoholic beverages
  • Transport on a 8 seat minivan
  • Visit of Siena with free time to explore
  • Snacks
  • Visit of Montepulciano with free time to explore
  • Visit of Cortona with free time to explore
  • Your local Tour leader providing directions, stories and info about all places.

Not Included

  • Gratuities
  • Guided walking tours of the 3 villages

Important Information

  • Not recommended for pregnant travelers
  • Not recommended for travelers with poor cardiovascular health
  • Travelers should have at least a moderate level of physical fitness
  • Please note that this tour involves a fair amount of driving due to the distance of these villages.
  • The order of the stops may change to ensure the best experience possible
  • Please note, the tour requires a minimum of 4 participants. If not reached, a private option with a supplement will be offered.
  • Not recommended for travelers with walking disabilities

Itinerary

1 Meet your local tour leader by Porta Romana, central Florence at 07:45am ready to leave by 8:00am.

Travel for an hour and a half on board of a private 8 seat mini-van through the beautiful Tuscan countryside enjoyed by generations on the movie screen while listening to stories and info about the area from your tour leader.

Duration: 90 minutes

2 Our first destination is the charming hilltop town of Cortona, famous for...

Our first destination is the charming hilltop town of Cortona, famous for its olive groves and immortalized by Diane Lane in Under the Tuscan Sun. Explore independently the town with its narrow streets, artisan stores, and landmarks featured in Frances Mayes' beloved novel. Who knows, you might even start your own Italian love story!

Duration: 60 minutes

3 Next, we travel just 40 minutes from Cortona to a picturesque local...

Next, we travel just 40 minutes from Cortona to a picturesque local farm nestled in the heart of Tuscany. Here, Cinta Senese pigs roam semi-wild, thriving on natural feed. Stroll among olive trees and vineyards before savoring the farm's exceptional products in a tasting board we have organised for you —cured meats and bruschetta made from garden-fresh ingredients, paired with their own wine. This unforgettable experience will leave lasting memories.

Duration: 90 minutes

4 We then head to the famous MONTEPULCIANO , where vampires converge in...

We then head to the famous MONTEPULCIANO , where vampires converge in Twilight Saga: New Moon. This beautiful walled town is also home to the renowned Montepulciano DOCG wine. Your tour leader will provide during the journey local insights, information about specific film scenes, and other attractions of Montepulciano, allowing you free time to explore the town at your leisure. Located near the entrance of the village is a 14th-century underground cellar where you will be able to enjoy a complimentary tasting of local wines and products they offer to the guests.

Duration: 120 minutes

5 After exploring Montepulciano, unwind in our comfortable van as we journey through...

After exploring Montepulciano, unwind in our comfortable van as we journey through the breathtaking Val d'Orcia. Marvel at the stunning landscapes, rolling hills, and iconic cypress trees. With ample time to relax, you can fully immerse yourself in the beauty of this enchanting region.

Duration: 90 minutes

6 Our last stop is the Medieval town of Siena, the backdrop for...

Our last stop is the Medieval town of Siena, the backdrop for movies like Letters to Juliet and Stealing Beauty. Prepare to be amazed by Siena's charm, with its narrow streets, local artisans, and medieval squares glowing in the setting sun. Your tour leader will escort you from the parking spot to the main piazza passing by the center. From there you will have 1hour approx free time to wander around.

Duration: 110 minutes

7 We will have then 1 hour approx ride and we will finally head back to Florence for approximately 8:00pm

📍 Meeting Point

Starting Point

Are you staying in Chianti or San Gimignano? Join the tour from our office Tuscany on Wheels located on Strada di Sant'Appiano 9/i. You can park your car for free!

End Point

Are you staying in Chianti or San Gimignano? Join the tour from our office Tuscany on Wheels located on Strada di Sant'Appiano 9/i. You can park your car for free!
Meet us in Piazza della Calza right in front Porta Romana at the blue P ( parking ) sign at 08:00am.

Frequently Asked Questions

This tour has a specific cancellation policy. We recommend checking the terms at the time of booking to understand the refund conditions.

You will receive your confirmation via email immediately after booking. Viator sends your voucher as soon as payment is completed.

The expected duration is approximately 12 hours. We recommend arriving at least 10-15 minutes before the departure time.

The tour price includes:

  • Stop at a 14th century cellar with possibility to have a complimentary wine and cheese tasting
  • Transport on a 8 seat minivan
  • Visit of Siena with free time to explore
  • Tastings at a local Farm based on cured meats and bruschetta made from garden-fresh ingredients, paired with their own wine
  • Visit of Montepulciano with free time to explore

...and more

The starting point is: Are you staying in Chianti or San Gimignano? Join the tour from our office Tuscany on Wheels located on Strada di Sant'Appiano 9/i. You can park yo.... We recommend using Google Maps to easily reach the meeting location.

We recommend bringing comfortable shoes, water, sunscreen, and a camera. Check the tour's additional information for any specific requirements.

Lowest Price Guarantee Free Cancellation Instant Confirmation
Best dates fill up quickly — check availability now
From €171.00 per person
See Available Dates →
You will be redirected to the official booking page to check real-time availability. No payment required at this stage.
Rated 4.9/5 by 122 verified travelers
€171.00 /person