a small intimate spot with a surprisingly upscale menu. The husband/wife owners are passionate about what they do and it shows. Excellent wine list. On the main piazza in Gaiole. Via Bettino Ricasoli, 53; 0577 553194; reservations a must
traditional Tuscan dishes simply, but carefully prepared. On the main piazza in Gaiole. Via Bettino Ricasoli 58/60; 0577 559987
a Gaiole institution now run by the third-generation of the Bianchi family. Pizza (served only in the evening) is the specialty, but there are also excellent pastas and meat dishes. Don’t miss the homemade tiramisu. On the main piazza in Gaiole. Via Bettino Ricasoli, 44; 0577 749501
part of the Tenuta Perano winery owned by the Frescobaldi family, the osteria is an upscale destination popular with wine tourists. Beautiful décor, professional service and commanding views of the surrounding countryside. About 3 kilometers outside of Gaiole, not far from the small village of Vertine. Strada di San Donato in Perano; 0577 749563
Gaiole’s local enoteca/wine bar is owned by our family friend, Riccardo, and is the go-to local spot for aperitivi, wine and light snacks. Don’t miss it. On the main piazza in Gaiole directly across from La Voglia Osteria. Via Bettino Ricasoli, 33
If you’ve never been to this part of Tuscany, you may want to see some of the area’s more well-known nearby cities and towns. That would certainly include Siena (1/2 hour drive from Gaiole); San Gimignano (about 1 hour from Gaiole); and Monteriggioni (close to San Gimignano). Closer by, the hilltop towns of Radda, Volpaia and Castellina are also well worth a visit.
the birthplace of Chianti and the home/estate of the Ricasoli family. Tours of the family estate and on-site tasting room. Lunch options include both an upscale restaurant and a simple bar serving sandwiches and small plates. Località Brolio, Gaiole-in-Chianti; www.ricasoli.com; advance reservations recommended.
One of Chianti’s best and most iconic producers. Architecturally evocative tasting pavilion; on-site restaurant; and bonus: a series of contemporary art installations throughout the ancient “borgo” that is part of the winery property. Reservations are a must. www.castellodiama.com
this local museum, located in the former cantina of the Ricasoli family just outside of the main piazza, is a deep dive into the town’s Etruscan origins and its rich history of wine production. There are also areas dedicated to the history of the local Eroica cycling race, and a permanent exhibit of works by the artist Cesare Olmastroni who created many beautiful images of the town and surrounding area during his lifetime. Purchase tickets in advance or on-site. www.chiantiorigo.it
this whimsical outdoor collection of contemporary art installations is a surprise and a hidden gem in a region known more for renaissance art than modern sculpture. Located in the town of Pievasciata about 20 minutes by car from Gaiole. The walk through the park is relatively flat and easy. See: www.parcosculturechianti.it