Day Trips

Siena, Cortona, Montepulciano, and Val d'Orcia Small-Group Tour with Farm Tastings and Wine Cellar Visit

Travel in a small group by minivan with a local guide, including tastings at a Tuscan farm and a 14th-century wine cellar.
Explore the medieval gems of Cortona, Montepulciano, and Siena, with free time to wander at your own pace in each town.
Sample local specialties—cured meats, bruschetta, and wine—at a picturesque farm nestled in the Tuscan countryside.
Step into history with a visit to an underground wine cellar, enjoying complimentary wine and cheese tastings.
Admire the rolling landscapes of Val d'Orcia, a region celebrated for its beauty and iconic film locations.

Departure from central Florence
Round-trip minivan transportation
Local driver-guide
Tastings at a local farm
Visit to Cortona with free time
Orientation walk in Montepulciano with free time
Orientation walk of Siena with free time
Stop at 14th-century cellar for wine and cheese tasting

Tips & Gratuities
Hotel pick-up / drop-off
Guided walking tours in Siena, Cortona, and Montepulciano

These tickets can't be cancelled or rescheduled.

Meet your local tour leader by Porta Romana, central Florence at 07:45am ready to leave by 8:00am. Travel in the comfort of an intimate 8-seat luxury van with a passionate local driver-guide as you discover the enchanting towns and breathtaking landscapes that have starred in some of Hollywood's most beloved films. Stroll through the charming medieval streets of Cortona, where Diane Lane found a new beginning in Under the Tuscan Sun. Explore the elegant hilltop town of Montepulciano, featured in The Twilight Saga: New Moon, and indulge in a tasting of its world-famous Vino Nobile di Montepulciano. Visit stunning locations seen in The English Patient starring Ralph Fiennes and A Midsummer Night's Dream with Michelle Pfeiffer, then admire the iconic rolling Tuscan hills immortalized in Letters to Juliet. Pause for a relaxing lunch at a scenic winery overlooking the rolling vineyards of Montepulciano, where you'll enjoy regional specialties paired with the celebrated Vino Nobile di Montepulciano. Blending iconic film locations, medieval charm, breathtaking landscapes, and authentic Tuscan flavors, this intimate small-group tour offers an unforgettable journey into the heart of Tuscany. We will have then 1 hour approx ride and we will finally head back to Florence for approximately 8:00pm

Accessibility
- This experience is not wheelchair accessible.
- Strollers are not permitted on this tour.
- The tour is not recommended for travelers with walking disabilities.

Additional information
- The tour involves a fair amount of driving due to the distance between villages.
- The order of stops may change to ensure the best experience for all participants.
- A minimum of 4 participants is required for the tour to operate; alternatives or refunds will be offered if this minimum is not met.
- Hotel pick-up and drop-off are not included in this experience.
- For departures from Florence, the meeting point is Porta Romana, Piazza della Calza 1, Florence. Please arrive by 7:45am for an 8:00am departure. For departures from Chianti, the meeting point is the Tuscany on Wheels office, located on Strada di Sant'Appiano 9/I, Barberino Tavarnelle.

Your voucher will be emailed to you shortly.

Display the voucher on your mobile phone with a valid photo ID at the starting point.

Please check your final voucher for the starting point details & specific instructions.