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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 1,384 Hotels in Chianti Region
Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

Via del Puglia, 61, Figline Valdarno
4.5 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).

Villa I Barronci

Villa I Barronci

Via Sorripa 10, San Casciano in Val di Pesa
4.5 out of 5.0

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

Borgo Del Cabreo

Borgo Del Cabreo

Via Monte Fioralle Case sparse, 9, Greve in Chianti
0.0 out of 5.0

Situated in Greve in Chianti, this property is within 1 mi (2 km) of Wine Museum and Piazza Matteotti. Passignano Abbey and Church of Santa Maria Assunta are also within 6 mi (10 km).

Villa la Palagina

Villa la Palagina

Via Grevigiana 4, Figline Valdarno
4.0 out of 5.0

Located in the mountains, this family-friendly hotel is within 9 mi (15 km) of Franciscan Monastery of St. Francis, Fashion Valley, and Wine Museum. Museum of Terranuova Tuscany and Masaccio Museum of Sacred Art are also within 9 mi (15 km).

Locanda le Piazze

Locanda le Piazze

Localita Le Piazze 41, Castellina in Chianti
4.0 out of 5.0

Situated in Castellina in Chianti, this hotel is within 6 mi (10 km) of Casa Vinicola Luigi Cecchi, Archaeological Museum of Chianti, and The Rock of Staggia. Church of San Lorenzo and Magione Castle are also within 6 mi (10 km).

CDH Hotel Radda

CDH Hotel Radda

Strada Statale 429, Radda in Chianti
4.5 out of 5.0

Situated in a rural location, this spa hotel is 3.1 mi (4.9 km) from Castello di Radda Winery and within 6 mi (10 km) of Castello d'Albola and Casa Vinicola Luigi Cecchi. Archaeological Museum of Chianti and Church of San Sigismondo are also within 9 mi (15 km).

Palazzo San Lorenzo

Palazzo San Lorenzo

Via Gracco Del Secco 113, Colle di Val d'Elsa
4.5 out of 5.0

Located in Val d'Elsa, this spa hotel is within a 10-minute walk of Art in Color, Ranuccio Bianchi Bandinelli Archeological Museum, and Colle di Val d'Elsa Cathedral. Piazza Arnolfo di Cambio is 0.8 mi (1.3 km) away.

Il Borgo di Vescine

Il Borgo di Vescine

Località Vescine, Radda in Chianti
4.5 out of 5.0

Situated in a rural location, this hotel is 3 mi (4.8 km) from Casa Vinicola Luigi Cecchi and within 6 mi (10 km) of Archaeological Museum of Chianti and Castello di Radda Winery. Castello d'Albola and Church of Santa Maria Assunta are also within 9 mi (15 km).

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These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.