You booked this experience
Make your trip unforgettable

Siena, Montepulciano & Val d'Orcia: Scenic Tuscany Tour – Max 8

146 Reviews 4.92 out of 5 stars Based on 146 traveler reviews collected by Cool Shore Excursions and TripAdvisor | Recommended by 98% of reviewers |
Badge of Excellence |Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Florence, Italy
Don't miss out!
On average, this is booked 25 (0) days in advance.

12 hours (approx.)
Mobile ticket
Offered in: English

Overview

Discover the beauty of Tuscany on a relaxed small-group day trip from Florence, traveling comfortably in an 8-seater minivan with a passionate local tour leader.

Explore medieval Siena, capture the iconic cypress-lined landscapes of Baccoleno, and enjoy more time wandering the charming streets of Montepulciano, famous for its Renaissance architecture, breathtaking views, and Twilight: New Moon filming locations.

Along the way, visit a local farm to sample traditional Tuscan cured meats and garden-fresh bruschetta, accompanied by locally produced wine.

Experience Tuscany's picturesque towns, stunning countryside, and authentic local flavors at a comfortable pace, without feeling rushed.

What's Included

  • Snacks Tastings at a local Farm based on cured meats and bruschetta made from garden-fresh ingredients, paired with their own wine
  • Alcoholic beverages Stop at a 14th century cellar with possibility to have a complimentary wine and cheese tasting
  • Transport on a 8 seat minivan
  • Gratuities
  • Guided walking tours of the villages
See 4 moreSee 4 more

Meeting Location

Meeting point
End point

This activity ends back at the meeting point.

What To Expect

Book Online

Our secure website provides real-time availability, and free, no-hassle cancellations up to 24 hours before your tour begins.
Read more

Safe & secure Easy breezy Hassle‑free

Porta Romana

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.
Read more

1 hour 30 minutes Admission Ticket Free

Cortona

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!
Read more

1 hour Admission Ticket Free

Montepulciano

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.
Read more

1 hour 30 minutes Admission Ticket Free

Piazza Grande a Montepulciano

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.
Read more

2 hours Admission Ticket Free

Val D'Orcia

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.
Read more

1 hour 30 minutes Admission Ticket Free

Piazza del Campo

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.
Read more

1 hour 50 minutes Admission Ticket Free

Porta Romana (pass by)

We will have then 1 hour approx ride and we will finally head back to Florence for approximately 8:00pm
Read more
Show 6 more stops

Additional Info

  • Not recommended for pregnant travelers
  • Not recommended for travelers with poor cardiovascular health
  • Not recommended for travelers with walking disabilities
  • 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.

Frequently Asked Questions (7)

Q: What is the cancellation policy for the Siena, Montepulciano & Val d’Orcia: Scenic Tuscany Tour – Max 8?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (CET).This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund. Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

We're here to help.
Activity code: C-6821P16

Traveler Photos

Reviews

4.92
146 reviews

Average 4.92 out of 5 stars based on 146 traveler reviews collected by Cool Shore Excursions and partner sites such as Cool Destinations and TripAdvisor

5 stars
138
4 stars
5
3 stars
3
2 stars
0
1 star
0
Don't miss out!
On average, this is booked 25 (0) days in advance.

Similar Tours & Activities

Accademia & Uffizi: Entry tickets & self-guided visit app

Do not miss the chance to explore two of the most famous Museums in the world in a completely independent way, guided by the audio …More

Do not miss the chance to explore two of the most famous Museums in the world in a completely independent way, guided by the audio...

2 to 4 hours
5.0 (4)
from
$109

Francy's Pasta & Gnocchi on the Hills with Florence view

I'm Francesca, passionate about cooking and gastronomy. I learned the art of fresh pasta from my grandmother in her pasta shop, where we started to …More

I'm Francesca, passionate about cooking and gastronomy. I learned the art of fresh pasta from my grandmother in her pasta shop, where we started to...

3 hours 15 minutes Free Cancellation
5.0 (511)
from
$142

Exclusive Uffizi Gallery Private Visit

The Uffizi Gallery is the most famous museum in Florence, Italy and the whole world, given the extensive amount of artwork and masterpieces housed such as …More

The Uffizi Gallery is the most famous museum in Florence, Italy and the whole world, given the extensive amount of artwork and masterpieces housed such as...

3 hours Free Cancellation
4.9 (14)
from
$146

Pisa Afternoon Tour from Florence + Skip-the-Line Access

Embark on an unforgettable journey to Pisa, where history and architecture intertwine to create a mesmerizing experience. Our expert guides will lead you through the …More

Embark on an unforgettable journey to Pisa, where history and architecture intertwine to create a mesmerizing experience. Our expert guides will lead you through the...

5 hours 30 minutes Free Cancellation
4.3 (6)
from
$160

Travelers Who Bought This Tour Also Bought

Skip the line David Guided Experience

Accademia is a very small museum and does not allow more than 600 people inside, for this reason the queue can vary from 3 to …More

4.8 (1,148)

Skip the line David Guided Experience

4.8 (1,148)

Accademia is a very small museum and does not allow more than 600 people inside, for this reason the queue can vary from 3 to...

1 hour Free Cancellation
4.8 (1,148)
from
$33

Half-Day Chianti Wine Tasting from Florence with Two Wineries

Discover the best of Tuscany with a Chianti Wine Tour from Florence, a top-rated experience combining wine tasting, scenic countryside, and authentic Italian flavors. Travel …More

Discover the best of Tuscany with a Chianti Wine Tour from Florence, a top-rated experience combining wine tasting, scenic countryside, and authentic Italian flavors. Travel...

5 hours 30 minutes Free Cancellation
4.6 (4,426)
from
$63

Private Golf Cart Tour: Michelangelo & Florence Hills

Explore Florence's hills on a small-group electric golf cart tour, along exclusive routes that reveal breathtaking panoramic views and a quieter, more authentic side of …More

Explore Florence's hills on a small-group electric golf cart tour, along exclusive routes that reveal breathtaking panoramic views and a quieter, more authentic side of...

1 hour 30 minutes Free Cancellation
4.7 (1,852)
from
$71

Special Entry & Guided Tour of Michelangelo’s David in Florence

Spiritual awakening by Michelangelo: discover the red thread that links David to the Sistine Chapel! This is not standard experience above David , this is …More

Spiritual awakening by Michelangelo: discover the red thread that links David to the Sistine Chapel! This is not standard experience above David , this is...

1 hour 20 minutes Free Cancellation
5.0 (1,274)
from
$31

What's Included

Activity name

  • SnacksTastings at a local Farm based on cured meats and bruschetta made from garden-fresh ingredients, paired with their own wine
  • Alcoholic beveragesStop 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
  • 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.
  • Gratuities
  • Guided walking tours of the villages

Additional Info

Activity name

  • Not recommended for pregnant travelers
  • Not recommended for travelers with poor cardiovascular health
  • Not recommended for travelers with walking disabilities
  • 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.
  • This tour/activity will have a maximum of 8 travelers

Report Product Issue

Activity name