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Chianti Region Vacation Packages

Take a sightseeing trip of Tuscany's renowned wine region and visit its vineyards, wineries, ancient churches, castles and hilltop villages.

The Chianti region’s mastery of the grape has made it one of the most famous wine regions of the world. Its wine-growing countryside is simply beautiful with miles of green hills, valleys, vineyards, olive groves and ancient forests. Dotted throughout the landscape are medieval villages with old churches, castles and towers. Tour centuries-old settlements, hike or cycle through the scenic countryside and sample Chianti wines, from new varietals to old favorites.

Chianti has been producing wines for more than 2,000 years, reaching prominence as a wine region in the 13th century. Its best-known appellation is the Chianti Classico, which dates back to 1716. Enjoy tasting sessions in wine bars, restaurants and tours of the region's wineries. No matter where you are staying in Chianti, there will be a winery close to you. Guided tours of the region make traveling between wineries easy.

Spend some time in Chianti’s centuries-old villages. Tour Radda in Chianti, a medieval walled town. Visit the 15th-century fortress and Etruscan burial sites of Castellina in Chianti. At Greve in Chianti find an arcaded, triangular plaza bordered by historical buildings.

Although you can move around Chianti by train, bus and car, consider renting a bike for a cycling trip along country lanes. Combine your love of the outdoors with an appreciation of art at the Chianti Sculpture Park in Pievasciata. Among the oak trees are a number of installations by artists from all over the world.

Chianti is a region that loves to party and festivals, concerts and markets are held throughout the year. Savor the summer wine and food festivals in San Casciano, Tavarnelle and many other places. Visit Impruneta in the fall for its festival celebrating the harvest of the grape. Witness how Panzano in Chianti marks the start of spring with a procession in period costumes.

Reach Chianti by flying into Pisa or Florence and using a car or public transportation to explore the region’s history, medieval villages, vineyards and countryside.

Top Hotel Deals

See all 702 Hotels in Chianti Region
Castello di Spaltenna

Castello di Spaltenna

Via Spaltenna 13, Gaiole in Chianti
of 5, from 35 reviews
5.0 out of 5.0

Situated in Gaiole in Chianti, this spa hotel is within a 15-minute walk of Gaiole in Chianti Stadium and Church of San Sigismondo. Medieval Tower of Barbischio is 2.1 mi (3.3 km) away.

La Loggia Villa Gloria

La Loggia Villa Gloria

Località Maciallina, Castelnuovo Berardenga
of 5, from 20 reviews
3.0 out of 5.0

Located in Quercegrossa, this hotel is within 6 mi (10 km) of University for Foreigners of Siena, Stadio Artemio Franchi, and Siena Stadium. Palasport Mens Sana and Santa Maria alle Scotte Polyclinic are also within 6 mi (10 km).

Villa I Barronci

Villa I Barronci

Via Sorripa 10, San Casciano in Val di Pesa
of 5, from 26 reviews
5.0 out of 5.0

These hotel accommodations are located throughout the area in San Casciano in Val di Pesa.

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

Via del Puglia, 61, Figline Valdarno
of 5, from 45 reviews
3.0 out of 5.0

Located in the heart of Figline Valdarno, this hotel is 0.3 mi (0.5 km) from Franciscan Monastery of St. Francis and within 6 mi (10 km) of Museum of Terranuova Tuscany and Masaccio Museum of Sacred Art. Soffena Abbey and Fashion Valley are also within 9 mi (15 km).

Relais Villa Tavolese

Relais Villa Tavolese

221 Marcialla, Certaldo
of 5, from 15 reviews
3.0 out of 5.0

Located in Marcialla, this hotel is 2.3 mi (3.7 km) from Santa Lucia al Borghetto Church and within 6 mi (10 km) of Tenuta Maiano and Vine and Wine Museum. Museum of Sacred Art and Casa del Boccaccio are also within 9 mi (15 km).

Top Flight + Hotel Deals

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