See Siena, Cortona & Montepulciano on a Day Trip


See Siena, Cortona & Montepulciano on a Day Trip

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

Visit Iconic Film Locations in Italy’s Tuscan Towns…

Are you ready to explore beautiful Tuscan towns from famous movies, enjoy lunch in Montepulciano, and taste wine all on a day trip from Florence? Then our Siena, Cortona, and Montepulciano tour is for you!

Wander the winding streets of Cortona once 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 flavors of Montepulciano wine.

Explore the locations made famous by Michelle Pfieffer in A Midsummer Night’s Dream and Ralph Fiennes in The English Patient, then spot the iconic rolling hills of Tuscany from Letters to Juliet. Finally, you will taste the local lifestyle by sampling fine local wine, cheese, and other products from the region — Tuscany is unquestionably one of Italy’s greatest foodie regions.

You can discover even more of this beautiful Italian region on our Multi-Day Tours of Tuscany. Whether you are keen to discover Tuscany through your tastebuds on the Great Escape Winery Tour or want to see the cities of Florence, Cinque Terre, and Pisa on a Multi-Day Trip of Tuscany, we have the perfect tour waiting for you!

Any questions? Don’t hesitate to get in touch.

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"

Montepulciano Tour Highlights

  • 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

Your Tuscan Towns Tour Itinerary

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.

Join our local guide for a private mini-van journey through Tuscany’s picturesque countryside, celebrated in many films. Discover the Italian lifestyle, traditions, cuisine, and more with insights from your guide en route to Siena. This medieval town, famed for its role in “Letters to Juliet” and “Stealing Beauty,” enchants with its narrow artisan streets and the iconic red-brick squares. Don’t miss the gothic Siena Cathedral before we proceed.

Next, we visit Montepulciano, known for “Twilight Saga’s New Moon” and for its Montepulciano DOCG wine. Enjoy a wine tasting and explore local products in a 14th-century cellar, with opportunities to buy unique gifts or ship them home. Your guide will share insights into the movie scenes filmed here, allowing free time to explore more town attractions.

Lunch is in a local restaurant in Montepulciano, set in a captivating cellar where Tuscan hospitality meets the rich flavors of local wines paired with traditional Tuscan dishes. Discover the cellar’s underground tunnel, possibly an ancient Etruscan site, adding a historical twist to your meal.

Our final stop is Cortona, the olive grove-dotted hilltop town made famous by “Under the Tuscan Sun.” Enjoy free time to wander its narrow lanes, visit artisan shops, and see landmarks from the film, perhaps starting your own Italian romance story.

This 12-hour tour blends cinematic history with authentic Tuscan culture for an unforgettable experience.

Still not made up your mind on which Florence experiences you want to enjoy most? Explore our Multi-Day Tours of Tuscany and Day Tours in and Around Florence.


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.


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