Search for a place or activity
Things to do in Chianti

Itineraries for Your Trip to Chianti

Chianti locals share their perfect days.
Find your Chianti itinerary

3 Days in Chianti for Foodies

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

Chianti’s picturesque countryside of vineyards, olive groves, and thick oak woods is where some of Tuscany’s most beloved specialties are produced, from bold red wines and peppery extra-virgin olive oil to heirloom pork and beef, pecorino sheep cheese, and truffles. This is the epicenter of the region’s rustic traditional food and wine—and a blockbuster destination for traveling foodies.

I’m lucky to live within striking distance of this beautiful region. We often pop into Tuscany for a weekend of feasting on hearty plates of pappardelle tossed with hare or wild boar ragù, grilled fiorentina steaks, and other rib-sticking delights. Eat and drink your way through Chianti in three days with these insider suggestions.

Spring and fall are the best times to visit both for the weather and for the seasonal cuisine.

If you only have time for one thing, visit a boutique winery to sip Chianti Classico while gazing over the hills where it's produced.

Day 1

Kick off your trip in the heart of the Chianti Classico wine country, visiting the tiny hilltop villages of Greve in Chianti with its unique main square, Panzano with its fortress, and Castellina with its historic town walls, plus other hamlets like Radda in Chianti and Gaiole in Chianti. Stop for wine tastings and to feast on a Tuscan lunch at a countryside or village trattoria. Meat lovers should book lunch at Solociccia in Panzano, the restaurant of celebrity Tuscan butcher Dario Cecchini.

Spend the evening connecting with a local host for a cooking demonstration and dinner. Learn how traditional local dishes are prepared from scratch, then enjoy casual conversation over a family-style dinner.

Day 2

One of Chianti’s most prized local delicacies is the black truffle, so this morning join an expert forager and trained pups for a truffle hunt in the Tuscan woods. Cap off your experience with a truffle-themed lunch paired with local Chianti wines at a farm-to-table countryside restaurant.

This afternoon, visit the medieval hill town of San Gimignano at the far western reaches of Chianti, stopping on the way at a family-run olive farm for a tour and tasting. In San Gimignano, learn how to make fresh pasta in a local farmhouse kitchen—or sit down for dinner and wine at a local winery.

Day 3

Travel to the far southern reaches of Chianti today to visit Siena and its surrounding countryside. Begin with a food tour through the medieval old town to take in its main square, cathedral, town hall, and other landmarks while snacking on a variety of local sweet and savory treats.

End your time in Chianti with an aperitivo experience on board a vintage Fiat 500. Enjoy the scenic countryside paired with a drink and nibbles.

See more things to do in Chianti