Tours/Florence/Siena, Cortona, Montepulciano & Val D'Orcia – Minivan Tour, Max 8
Viator · group up to 8 pax

Siena, Cortona, Montepulciano & Val D'Orcia – Minivan Tour, Max 8

4.9(125)Florence1 hour
VIATOR4.4(18)TRIPADVISOR4.9(107)

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.

Tour Options

From Florence: Classic Tour
  • Departure Point: Central Florence, Piazza della Calza 1, by the "P" parking sign at 8:00am. Small group tour (max 8 people) Starting point: Parcheggio Oltrarno, Piazza della Calza, 1, 50125 Firenze FI, Italy
From Chianti: Classic Tour
  • Departure Point: Tuscany on Wheels office, located on Strada di Sant'Appiano 9/I- Barberino Tavarnelle ( FI ). Small group tour (max 8 people) Starting point: Tuscany on Wheels - Tours in & from San Gimignano, Strada di Sant' Appiano, 9/i, 50028 Barberino Tavarnelle FI, Italy
Private Tour
  • Private 8 seat minivan Starting point: Parcheggio Oltrarno, Piazza della Calza, 1, 50125 Firenze FI, Italy

Itinerary

90 min

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.

60 min

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!

90 min

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.

120 min

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.

90 min

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.

110 min

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.

Pass by

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

Highlights

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
Visit of Cortona with free time to explore
Your local Tour leader providing directions, stories and info about all places.

What's included

Included
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
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

Traveller Ratings

4.9
125 reviews
5
116
4
5
3
1
2
1
1
2

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

Reviews(125)

3
330cherieg
August 7, 2026
Great tour

Great tour through beautiful countrysides and charming towns.

9
978amberr
July 27, 2026
The best tour!!

We had the absolute best time during our tour! Our tour guide, Dom, was so helpful, engaging, and accommodating. We really could not have asked for a better experience. I would 100% recommend!

G
G3543XZoliviad
July 27, 2026
Wonderful Experience

This was such a wonderful experience! Each location was absolutely beautiful, and our guide, Dom, was so kind and knowledgeable. 10/10 recommend!

P
Paradise15048851286
July 5, 2026
Best tour and guide ever!

This trip was the best for me 🫶🏾🥺🙏thanks so much to Alberto!!!! He is amazing

Operator response

Thank you so much for your lovely review! We’re truly happy to hear that this trip was such a special experience for you. It’s wonderful to know that Alberto, your tour leader, made the day so memorable. We’ll be sure to pass along your kind words to him. We hope to welcome you back for another unforgettable adventure soon!

X
X9538XLsallyh
July 3, 2026
Great Tour!

Wonderful! Highly recommend!

Operator response

Thank you so much for your wonderful review and recommendation! We’re delighted to hear that you had such a great experience, and we hope to welcome you back to Tuscany again soon!

N
nayirib
July 3, 2026
Great day trip from Florence!

Amazing day with Antonello! Beautiful trip to Siena, Montepulciano and Cortona!

Operator response

Thank you so much for your wonderful review! We’re delighted to hear that you had such an amazing day exploring Siena, Montepulciano, and Cortona. It’s especially lovely to know that Antonello, your tour leader, made the experience so enjoyable. We’ll be sure to pass along your kind words to him, and we hope to welcome you back to Tuscany again soon!

L
laurenjQ5704PL
July 3, 2026
Amazing Tuscany tour

Tony was an amazing tour guide! Gave us a great day of family adventures

Operator response

Thank you so much for your lovely review! We’re delighted to hear that you had such a wonderful day filled with family adventures. It’s especially great to know that Antonello, your tour leader, made the experience so enjoyable and memorable. We’ll be sure to pass along your kind words to him, and we hope to welcome you and your family back to Tuscany again soon!

R
robineA976SV
June 24, 2026
Beautiful day trip

Wonderful day drip with family. Beautiful scenery

Operator response

Thank you so much for your lovely review! We’re delighted to hear that you and your family had such a wonderful day and enjoyed the beautiful Tuscan scenery. We truly appreciate your feedback and hope to welcome you back for another memorable experience in Tuscany!

4
485terrik
June 10, 2026
Worth doing to see places you may never see otherwise

It was wonderful. Very interesting. The lunch was fantastic. The guide, Tony was very knowledgeable. Long but worthwhile day. You will see beautiful places

Operator response

Thank you so much for your wonderful review! We are delighted to hear that you had a wonderful and interesting experience, and that you enjoyed the fantastic lunch and the beautiful places along the way. We truly appreciate your kind words for Antonello, your tour leader, and we are so happy that his knowledge helped make the day worthwhile. Thank you again for joining us, and we hope to welcome you back for another memorable experience in Italy!

D
danielyV3734FP
April 25, 2026
A great day.

This was a wonderful experience. A true highlight of our 2+ week honeymoon. We loved our guide Ned! He did a great job leading us through all of these amazing places while being very informative and fun to hang out with for the whole day. The visit to Roberto’s farm in Val D’Orcia was very special; such hospitality in such a magical place. Highly recommend!

Operator response

Thank you so much for your beautiful review! We’re truly honored to hear that this experience was one of the highlights of your honeymoon. It’s wonderful to know that your tour leader Nedas made the day both informative and enjoyable while guiding you through such amazing places. We’re especially happy that your visit to Roberto’s farm felt so special and memorable. The hospitality and beauty of that area truly make it magical. Thank you again for choosing to spend part of your honeymoon with us, and we wish you both many more wonderful adventures together!

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