Siena Cortona Montepulciano and Val D’orcia


Siena Cortona Montepulciano and Val D’orcia

  • 1 Day
  • 4 - 8 People
  • All year round

Explore the most beautiful Tuscan towns made famous through movies and enjoy a light lunch in 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 Montepulciano, and taste the famous Noble of Montepulciano wine.

Explore the locations made famous by Michelle Pfieffer in “A Midsummer Night’s Dream” and Ralph Fiennes 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.

Price Includes

  • Round trip transportation
  • Your informative IOAB tour leader
  • Orientation walk of Montepulciano and free time
  • 1h free time to explore Cortona
  • Orientation walk of Siena and free time
  • Light lunch in a local winery including 2 wine tasting including the famous " vino nobile di Montepulciano"


  • Transport by private 8-seater mini van
  • Small groups with a local guide
  • Travel through the iconic Tuscan countryside
  • Visit three historic Tuscan towns
  • See the locations of seven movies
  • Enjoy a light lunch overlooking stunning scenery
  • Taste local wine and food products
  • Maps, information and recommendations only locals know


Meet your local tour leader to travel by private 8 seat mini-van through the beautiful Tuscan countryside enjoyed by generations on the movie screen.

Learn about the Italian way of life, the local customs, cuisines and quirks from your guide before reaching the first stop of the day. SIENA is the medieval town that set the backdrop of the famous movie Letters to Julliet and Stealing beauty. Be ready to be amaized by Siena a town full of charm, narrow streets with local artisans and medieval squares made in red brigs. A stop of the gotic Cathedral of Siena will be a must before we continue our trips towards our next destination.

From here, you head to the famous MONTEPULCIANO, where vampires converge in the Twilight Saga’s New Moon. The beautiful walled town is also the home of the Montepulciano DOCG WINE, making it the perfect opportunity for a tasting of vino and other local products at an ancient underground cellar from the 14th century. You will have the chance to purchase products for the perfect gift or to ship home. Your guide will provide you with a local insight, information about the specific scenes and other films set in each place, as well as free time to explore the other attractions that the the towns have to offer at your leisure.

Right inside Montepulciano, we will find our local restaurant located in a stunning position, in a cellar where time seems to have stopped, letting oneself be seduced by the extraordinary Tuscan hospitality and the enveloping taste of the wines that perfectly match the flavor of the typical products. The visit to the Cellar reserves other surprises such as the long underground tunnel recently discovered and made partially practicable, which, from the traces found, could have been part of an Etruscan tomb or one of the many underground tunnels that connected the city to outside to allow escape routes during sieges. Here we will enjoy our LIGHT LUNCH with local Tuscan products including WINE TASTING.

After lunch you will head to CORTONA, the luscious hilltop town known for its olive groves and made famous by Diane Lane in Under the Tuscan Sun. You will be given free time in Cortona to explore the narrow streets, artisan stores and other landmarks seen in the cinematic adapation of Frances Mayes’ novel. Who knows, maybe your own Italian love story will unfold!

DURATION: 12 hours


Meeting Point

Florence: Piazza della Calza, right in front Porta Romana at the blue P (parking) sign.

San Gimignano area: Tuscany on Wheels office, Strada di Sant’ Appiano 9/i – Barberino Tavarnelle



From Florence at 8:00am, from Chianti area at 8:45am.


Save To Wish List

Adding item to wishlist requires an account