- Day trip to Tuscany’s hill towns from Siena
- Explore San Gimignano by foot and admire its medieval towers
- Stop for lunch and Chianti wine at a Monteriggioni winery
- Travel through the idyllic Val d’Orcia region
- Sample Brunello di Montalcino wine in Montalcino
Departure & Return
If pickup is not required please meet our staff in front of Bar La Lizza, Via Sasso di S. Bernardino, 7, 53100 Siena SI
Return DetailsReturns to original departure point
What To Expect
Your first stop in the region is the beloved hill town of San Gimignano, a UNESCO World Heritage Site. Enjoy free time here to wander the streets of its historical center, gazing at the medieval architecture, towers, piazzas, and artisan shops. San Gimignano produces the renowned vernaccia wine, and you’ll find plenty of enoteche (wine shops) around the streets.
Next, you’ll head to the historic fortress town of Monteriggioni. The hill town is encircled by intact medieval walls, beautifully preserved from the 12th century. Hear how Dante likened the walls’ towers to the Giants of Inferno in his Divine Comedy as you enter the town, then make your way to a winery for lunch. Savor a light meal of local cheese and salami, paired with Chianti wine.
With your appetite sated, you’ll travel into the Val d’Orcia region of Tuscany where the winemaking village of Montalcino awaits. Taste the esteemed Brunello di Montalcino wine, and learn about the town’s winemaking traditions.
Relax on the journey back to Siena, and finish your day trip with a hotel drop-off.
- Confirmation will be received at time of booking
- Customers must be able to climb and descend stairs. A small amount of walking is involved to reach Monteriggioni Castle as it is uphill.
- Pickup and drop off are included for Hotels located within 20km from the center Siena. If your accommodation is outside, please consider that the meeting point will be from: Siena, Piazza Gramsci in front of Bar La Lizza
- Vegetarian option is available for lunch, please advise any specific dietary requirements at time of booking
- Not wheelchair accessible
- Stroller accessible
- Near public transportation
- Infant seats available
- Most travelers can participate
- This tour/activity will have a maximum of 8 travelers
- OPERATED BY myTour in Italy
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
- This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
Learn more about cancellations.
- Face masks required for travelers in public areas
- Face masks required for guides in public areas
- Face masks provided for travelers
- Temperature checks for travelers upon arrival
- Hand sanitizer available to travelers and staff
- Regularly sanitized high-traffic areas
- Gear/equipment sanitized between use
- Transportation vehicles regularly sanitized
- Social distancing enforced throughout experience
- Guides required to regularly wash hands
- Regular temperature checks for staff
- Paid stay-at-home policy for staff with symptoms
See all safety measures taken by San Gimignano, Chianti, and Montalcino Day Trip from Siena.