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Things to do in Siena

Itineraries for Your Trip to Siena

Siena locals share their perfect days.
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3 Days in Siena for Foodies

Curated by Rebecca WinkeItalophile and travel enthusiast who’s lived in and written about Italy for more than two decades.

Siena’s central location between the Chianti, Val d’Orcia, and Crete Senesi areas of Tuscany means that the UNESCO-listed medieval city is also a foodie paradise. Vineyards producing wines like Vino Nobile di Montepulciano and Brunello di Montalcino are within striking distance, as are hyper-local specialties like Pienza’s pecorino cheese, earthy black truffles and aromatic olive oil from Chianti, and charcuterie made from Siena’s heirloom Cinta Senese pork.

When I want to indulge in a Tuscan foodie break, I settle for a few nights in Siena. From here, it’s easy to cast my gourmet net wide and enjoy the best of the region. Here’s how to spend three days enjoying dining and imbibing Tuscany’s delights from Siena.

Siena and the surrounding countryside are scorching in the summer months, so avoid vineyard visits during the midday hours.

If you only have time for one thing, take a wine tour through the hills of Chianti, Val d’Orcia, or the Crete Senesi.

Day 1

Start your trip by exploring Siena’s local cuisine in the heart of its medieval old town. Admire the main Piazza del Campo square, soaring Gothic cathedral, and other UNESCO-listed landmarks while stopping to sample sweet and savory specialties from local eateries and gourmet shops.

Skip the restaurant dinner tonight and instead connect with a local for a cooking demonstration and family-style meal in their home. Relax over dinner and wine while learning more about the city and its culinary culture.

Day 2

Today, head just north of Siena to explore the Chianti countryside and its gourmet delights. Begin with a morning truffle hunt led by an expert forager and trained pups to unearth precious black truffles in the Tuscan woods. Celebrate your success with a truffle-themed lunch paired with local wines.

Dedicate your afternoon to the best of Chianti’s wine country. Join a guided tour with transportation so you can imbibe worry-free and visit a number of the area’s most storied wineries for tours and tastings as the sun begins to dip behind the vineyard-covered hills.

Day 3

The Val d’Orcia, home to some of Tuscany’s flagship wines and foods, stretches out to the south of Siena. Today head to Pienza to try its distinctive pecorino sheep cheese, then sample wines from nearby Montepulciano and Montalcino at the tiny boutique wineries scattered across the countryside.

Cap off your trip with a sunset drive in a vintage Fiat 500 through the Crete Senesi hills just outside the city. Pause for a prosecco toast at a scenic overlook at dusk, then stop at a countryside restaurant for a true Tuscan dinner.

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