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Gaiole in Chianti Vacations

Pack those stellar shades. We have Gaiole in Chianti vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Gaiole in Chianti – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Gaiole in Chianti vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Gaiole in Chianti

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Gaiole in Chianti vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Gaiole in Chianti well.

Gaiole in Chianti Flight + Hotel packages

Top Hotel Deals

See all 131 Properties in Gaiole in Chianti
Castello di Spaltenna

Castello di Spaltenna

Via Spaltenna 13, Gaiole in Chianti
    5.0 out of 5.0
     
     

    Situated in Gaiole in Chianti, this spa hotel is within a 15-minute walk of Church of San Sigismondo and Gaiole in Chianti Stadium. Meleto Castle and Medieval ...

    Castello di Spaltenna$258

    Castello di Spaltenna$258
    Borgo Casa al Vento

    Borgo Casa al Vento

    Località Casa Al Vento - Barbischio, Gaiole in Chianti
       
       

      This family-friendly Gaiole in Chianti farm stay is within 3 mi (5 km) of Medieval Tower of Barbischio, Gaiole in Chianti Stadium, and Church of San Sigismondo. ...

      Borgo Casa al Vento$127

      Borgo Casa al Vento$127
      Castello di Meleto

      Castello di Meleto

      Localita Meleto, Gaiole in Chianti
         
         

        Situated in a rural location, this farm stay is 0.1 mi (0.1 km) from Meleto Castle and within 3 mi (5 km) of Gaiole in Chianti Stadium and Church of San Sigismondo. ...

        La Pieve Marsina

        La Pieve Marsina

        Loc. Argenina, Monti in Chianti, Gaiole in Chianti
           
           

          Located in the historical district, this family-friendly apartment building is within 6 mi (10 km) of Castle of Brolio, Chianti Sculpture Park, and La Fornace ...

          Castello di Tornano

          Castello di Tornano

          Loc. Tornano, Gaiole in Chianti
             
             

            Situated in a rural location, this farm stay is 4.4 mi (7.1 km) from Castle of Brolio and 9.8 mi (15.8 km) from Valdarno. Porta Camollia and Porta Romana are ...

            Castello di Tornano$245

            Castello di Tornano$245
            La Fonte del Cieco

            La Fonte del Cieco

            Via Ricasoli 18, Gaiole in Chianti
              3.0 out of 5.0
               
               

              Situated in Gaiole in Chianti, this hotel is steps from Gaiole in Chianti Stadium and Church of San Sigismondo. Medieval Tower of Barbischio and Meleto Castle ...

              La Fonte del Cieco$76

              La Fonte del Cieco$76
              Hotel Le Pozze Di Lecchi

              Hotel Le Pozze Di Lecchi

              Loc. Molinaccio, Gaiole in Chianti
                4.0 out of 5.0
                 
                 

                Situated in a rural location, this spa hotel is within 6 mi (10 km) of Cantalici Winery, Castle of Brolio, and Chianti Sculpture Park. La Fornace Art Gallery ...

                Hotel Le Pozze Di Lecchi$142

                Hotel Le Pozze Di Lecchi$142
                Gaiole Suites

                Gaiole Suites

                Via Alcide dé Gasperi, Gaiole in Chianti
                   
                   

                  Situated in a rural location, this apartment building is within a 10-minute walk of Church of San Sigismondo and Gaiole in Chianti Stadium. Meleto Castle and ...

                  Fattoria Castello Di Starda

                  Fattoria Castello Di Starda

                  Localita' Starda, 1, Gaiole in Chianti
                     
                     

                    Situated in a rural location, this apartment building is 1 mi (1.7 km) from Valdarno and within 9 mi (15 km) of Cantalici Winery and Meleto Castle. Church of ...

                    Fattoria Castello Di Starda$97

                    Fattoria Castello Di Starda$97
                    Villa Sofia

                    Villa Sofia

                    Via Marino 43, Gaiole in Chianti
                       
                       

                      Located in the historical district, this family-friendly villa is within 6 mi (10 km) of Chianti Sculpture Park, La Fornace Art Gallery, and Meleto Castle. Church ...

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.