The Palio di Siena is one of Italy’s most thrilling and historic festivals, held twice each summer in the medieval city of Siena, Tuscany.
This centuries-old tradition centers around a breathtaking bareback horse race in the city’s main square, the Piazza del Campo, where ten horses and riders—each representing a neighborhood or “contrada”—compete in a spectacle of speed, strategy, and community pride.
Far more than just a horse race, the Palio is an expression of Sienese culture, passion, and rivalry, celebrated each year on July 2 (Palio di Provenzano) and August 16 (Palio dell’Assunta).
In the days leading up to the event, Siena transforms into a living stage of medieval pageantry, with colorful parades, flags, and traditional costumes filling the streets. Each contrada marches proudly with musicians and flag-throwers, while horses are blessed in local churches before the race.
When the 90-second contest begins, the Piazza erupts in pure adrenaline, and afterward the celebrations continue late into the night with banquets, music, and gatherings across the city.
Sneak Peak:
If you want to get a feel for what Palio is like, there’s a terrific documentary on Netflix called Palio. Check it out.
What makes this a great group experience?
The traditions, festivals, parades, history, costumes, pageantry, and neighborhood rivalries make this a thrilling spectacle for ages 8 to 80.
It’s important to stay somewhere that balances convenience to Siena with the space and comfort a family or large group needs.
The following villas provide just that—giving you a Tuscan home where you can gather after the day’s excitement and celebrate together.
Antipasti on the Patio is only 15 minutes from Siena’s Piazza del Campo, so you won’t feel far from the action, but once you’re back at the villa, it feels like your own private corner of Tuscany.
With space for up to fourteen guests across six bedrooms, it works really well for families or a group of friends who want to experience Palio together.
The house itself has that rustic Tuscan charm—stone walls, terracotta floors, wooden beams—yet it doesn’t skimp on modern comforts like air-conditioned bedrooms and a proper kitchen where you can cook together.
What I love most about this place are the outdoor spaces. You can share long meals under the loggia, make pizzas in the wood-burning oven, or even grab some fresh vegetables straight from the garden.
The pool is perfect for cooling off on hot summer days, and there’s a hot tub waiting for you in the evening when you just want to relax.
There’s even a small gym if you’re the type who likes to squeeze in a workout, though honestly, lounging with a view of the Tuscan hills might be more tempting.
Just outside delightful Monteriggioni and 20 minutes from Siena, this villa is one of those rare finds tailor made for a group celebration.
With 16 bedrooms and space for up to thirty-two guests, it’s designed for multi-generational gatherings, milestone celebrations, or friends’ reunions.
The setting has that rustic Tuscan charm you’d expect, but it’s paired with modern comforts that make a stay feel effortless, from a professional kitchen perfect for group meals to plenty of dining and lounge areas where people can spread out but still feel connected.
The outdoor spaces are just as inviting. There’s a private pool where you can cool off after a hot Palio day, plenty of terraces for lingering over wine and conversation in the evening, and gardens that set the scene for quiet walks or casual group hangouts.
What makes it special, though, is how well it’s set up for sharing experiences—you can gather everyone for long dinners, let the kids play while the adults relax, and still have enough space for quiet downtime when you need it. And Monteriggioni is an extra bonus.
