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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 1,978 properties in Chianti Region
Borgo Del Cabreo £165
Reviewed on 6 Apr 2019
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Borgo Del Cabreo

Borgo Del Cabreo

Via Monte Fioralle Case sparse, 9, Greve in Chianti
     
    4.9 of 5
    0.0 out of 5.0

    What a charming and extraordinary place. Great service and beautiful accommodations, loved it!

    Castello di Spaltenna £206
    Reviewed on 16 Oct 2018
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    Castello di Spaltenna

    Castello di Spaltenna

    Via Spaltenna 13, Gaiole in Chianti, SI
       
      4.7 of 5
      5.0 out of 5.0

      Beautiful location, stunning views, wonderful service. For a luxury resort the beds were terribly uncomfortable. Suggesting terrace for high end rooms was also misleading and not worth the price. The ‘casual’ restaurant is not casual at all and best to head into the centre for casual dining and ...

      Palazzo Leopoldo Dimora Storica & Spa £97
      Reviewed on 26 Apr 2019
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      Palazzo Leopoldo Dimora Storica & Spa

      Palazzo Leopoldo Dimora Storica & Spa

      Via Roma, 33, Radda in Chianti, SI
         
        4.6 of 5
        0.0 out of 5.0

        Lovely spacious grand room. Difficult parking Struggled up the hill with luggage. No offer of help from staff. A few problems with internet Nice location.

        Hotel Ristorante Alcide £51
        Reviewed on 2 Mar 2019
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        Hotel Ristorante Alcide

        Hotel Ristorante Alcide

        Viale Marconi, 67/A, Poggibonsi, SI
           
          3.9 of 5
          4.0 out of 5.0

          The man in the reception desk beniamyn his name give me an exelent service

          Tenuta Di Ricavo £125
          Reviewed on 12 Oct 2018
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          Tenuta Di Ricavo

          Tenuta Di Ricavo

          Località Ricavo, 4, Castellina in Chianti, SI
             
            4.7 of 5
            4.0 out of 5.0

            Owner/Manager is lovely welcoming woman who is very helpful and patient. Food is outstanding. Rooms are updated and spacious. We had a wonderful stay and the prices were reasonable for such high quality. Only issue is the rocky dirt entrance road. It needs grading. It is very rough.

            Agriturismo Papageno
            Agriturismo Papageno

            Agriturismo Papageno

            Via Verrazzano 71, Rignano sull'Arno
               
              4.0
              of 5, from 1 reviews
              2.0 out of 5.0

              Situated in Rignano sull'Arno, this agritourism property is 0.1 mi (0.1 km) from Valdarno and within 12 miles (20 km) of The Mall Luxury Outlet and Castello di Nipozzano. ObiHall is 11.3 mi (18.3 km) away.

              Salvadonica £257
              Reviewed on 28 Apr 2019
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              Salvadonica

              Salvadonica

                 
                4.7 of 5
                0.0 out of 5.0

                The place is much nicer than the photos. Wonderful staffs and owners, the restaurant is fantastic!

                Villa Sabolini £70
                Reviewed on 16 Jan 2019
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                Villa Sabolini

                Villa Sabolini

                Loc. Mensanello, Colle di Val d'Elsa, SI
                   
                  4.4 of 5
                  4.0 out of 5.0

                  Beautiful view and wonderful staff!

                  Top Deals on Flights

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