Food

Local Restaurants

Osteria Il Granaio (link)
AmorDivino (link)
Ischieto (link)

Wine

Vineyards

Fèlsina (link)
Azienda Agricola La Lastra (link)
Poggio Amorelli (link)

Site Seeing

Towns & Cities

Siena (35 mins drive from Rapolano)
San Gimignano (1 hr 10 mins)
Montepulciano (35 mins)

Pienza (40 mins)
Monteriggioni (45 mins)
Montalcino (45 mins)

Florence (1 hr 15 mins)
Vinci (1 hr 30 mins)
Arezzo (45 mins)

Activities

Sports

Tennis & Padel (link)
Golf (link)
Bicycle Rental (link)

Shopping

The Mall Firenze - Fashion Outlet (link)
Sugar - Arezzo (website) (location)
This street in Siena (link)

Palio di Siena

If you happen to be in Tuscany on Thursday 2 July 2026, you’ll witness something special; the Palio di Siena, a centuries-old horse race that takes over Siena’s main square, Piazza del Campo.

I (Max) went once, and it was the most intense and unforgettable sporting event of my life. Two minutes of pure chaos, passion, and history colliding in the middle of one of Italy’s most beautiful cities.

The race takes place twice a year, on 2 July and 16 August, and is unlike anything else in the world. Ten horses, each representing a different contrada (district of Siena), thunder around the packed square in a blur of colour, flags, and noise. The energy in the city is electric.

If you do want to attend, make sure you do your research. It’s not an event you can just show up to. However, it is 100% worth the effort.

Watch 2 minutes of absolute chaos (watch to the end, it’s worth it):

Learn More:

Wikipedia

New York Times

The Guardian

New Yorker

Vogue

Palio (Documentary) - (Amazon) (Netflix)

Pictures of the Piazza del Campo: Normal Day - Race Day