From Florence: Private Small-Group Tour of Siena, Cortona, Montepulciano, and Val d'Orcia with Local Tastings





Explore at your pace
Guided tour
Transfers available
- Round-trip transportation by comfortable minivan with a local English-speaking tour leader
- Free time to explore the medieval towns of Siena, Cortona, and Montepulciano
- Tuscan farm tasting with local cured meats, bruschetta, and regional wine
- Visit to a 14th-century underground cellar in Montepulciano with wine and cheese tasting
- Scenic drive through the UNESCO-listed Val d’Orcia, featuring rolling hills and iconic cypress-lined landscapes
- Round-trip transportation by comfortable minivan with a local English-speaking tour leader
- Visit to a local Tuscan farm with tastings of regional products
- Free time to explore the medieval hill town of Cortona
- Guided orientation walks and free time in Siena and Montepulciano
- Visit to a 14th-century underground cellar with wine and cheese tasting
- Guided walking tours in Siena, Cortona, and Montepulciano
- Car seat for kids under 150cm
- Hotel Pick Up/Drop Off
- Tips & Gratuities
These tickets can't be cancelled or rescheduled.
Discover Siena, Cortona, Montepulciano, and the UNESCO-listed Val d’Orcia on a small-group Tuscany day trip from Florence. Travel comfortably with a maximum of 8 guests as you explore medieval hill towns, scenic countryside, and some of Tuscany’s most iconic landscapes. Visit Siena’s historic center, stroll through the picturesque streets of Cortona, enjoy a wine tasting in Montepulciano, and admire the rolling hills of Val d’Orcia. Perfect for travelers seeking authentic Tuscan villages, renowned wines, panoramic photo stops, and a more personalized experience.
What to bring
- Kids under 150cm (approximately 4 ft 11 in) must use an appropriate car seat according to Italian law; please bring your own or inform the operator in advance to hire one for EUR 35 per seat.
- If you plan to use an inflatable car seat, ensure it has a European approval label, is suitable for your child’s weight and height, and can be installed correctly.
What's not allowed
- Pets are not permitted on this experience.
Accessibility
- This experience is not wheelchair accessible.
- Strollers are not permitted on this experience.
- This 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 guests.
- 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.
100% ticket guarantee
Receive tickets on time, for the experience you've booked.
100% experience guarantee
Get a refund if your experience doesn't happen as promised.
100% assistance guarantee
Available before, during, and after your trip.
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