Siena, Cortona, Montepulciano & Val d'Orcia Small Group Tour - Private Tours & Luxury Guided Experiences

Tour Overview

Visit Siena, Montepulciano, Cortona and Val D’Orcia with a stop in a local farm to sample some Local Tuscan products.

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.

What's Included

Round-trip transportation on an 8-seat minivanYour local Tour leader providing directions, stories, and info about all placesTastings at a local Farm based on cured meats and bruschetta made from garden-fresh ingredients, paired with their own wineVisit of Cortona with free time to exploreOrientation walk in Montepulciano with free time to exploreOrientation walk of Siena with free time to exploreStop at a 14th-century cellar with the possibility of having a complimentary wine and cheese tasting

What's Not Included

Guided walking tours in Siena, Cortona and Montepulciano
Tips or gratuity

Your Itinerary

Ready to Depart

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.

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!

Local Farm

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.

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.

Val d'Orcia Photo Stop

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.

Siena

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.

Back to Florence

We will have then 1 hour approx ride and we will finally head back to Florence for approximately 8:00pm Departure Points available for this tour: Florence: 08:00am - 8:00pm | 12h Address: Parcheggio Oltrarno , in front of the blue “ P” sign by Porta Romana , Piazza della Calza 1, Florence. Take me hereTuscany on Wheels: 08:45am - 7:00pm | 11.30h Address: Tuscany on Wheels office, Strada di Sant’ Appiano 9/i, Barberino Tavarnelle ( FI ). Take me here

Meeting Point

Florence: Parking Oltrarno, Piazza della Calza 1, right in front Porta Romana at the blue P (parking) sign, 50125 Firenze

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Cancellation Policy

Standard Viator policy

Additional Info

Minimum age 18+ years
Difficulty Moderate
Starts 08:00, 08:45
Language English
Group size Up to 8 people
Operated by Authentic Italy Adventures

Siena, Cortona, Montepulciano & Val d’Orcia Small Group Tour