Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Pico Island Vacations

Pack those stellar shades. We have Pico Island 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 Pico Island – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Pico Island 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 Pico Island

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 Pico Island 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 Pico Island well.

Top Hotel Deals

See all 89 Hotels in Pico Island
Aldeia das Adegas

Aldeia das Adegas

Rua das Adegas 3A, Sao Roque do Pico
    4.0 out of 5.0
     
     

    Situated near the beach, this apartment building is within 1 mi (2 km) of Convent of Sao Roque do Pico and Sao Roque Church. Caiado Lagoon and Museu do Vinho ...

    Hotel Caravelas

    Hotel Caravelas

    Rua Conselheiro Terra Pinheiro, 3, Madalena
      4.0 out of 5.0
       
       

      Situated on the boardwalk, this hotel is 0.7 mi (1.2 km) from Museu do Vinho and 2 mi (3.1 km) from Pico Island Vineyard Culture. Gruta das Torres and Peter's ...

      Casa do Comendador

      Casa do Comendador

      Rua de Baixo, No 17 S.Miguel Arcanjo, Sao Roque do Pico
        4.0 out of 5.0
         
         

        Situated by the ocean, this guesthouse is 1.2 mi (1.9 km) from Sao Roque Church and 2.4 mi (3.8 km) from Convent of Sao Roque do Pico. Caiado Lagoon and Lajes ...

        Sara Village

        Sara Village

        Estrada Regional Nº1 Nº20, Sao Roque do Pico
          3.0 out of 5.0
           
           

          Situated in Sao Roque do Pico, this country house is close to Sao Roque Church and Convent of Sao Roque do Pico. Area attractions also include Caiado Lagoon ...

          Aldeia dos Caldeirões

          Aldeia dos Caldeirões

          Rua dos Caldeirões, Madalena
             
             

            Situated in the mountains, this vacation home is within 9 mi (15 km) of Gruta das Torres, Pico Island Vineyard Culture, and Museu do Vinho. Mount Pico is 9.2 ...

            Baia Da Barca Apartamentos Turisticos

            Baia Da Barca Apartamentos Turisticos

            LUGAR DA BARCA,, MADALENA DO PICO
              3.0 out of 5.0
               
               

              Situated in Madalena, this apartment building is 0.4 mi (0.7 km) from Museu do Vinho and 2.3 mi (3.7 km) from Pico Island Vineyard Culture. Gruta das Torres ...

              A Casa do Ouvidor

              A Casa do Ouvidor

              Estrada Regional, 22, Sao Roque do Pico
                4.0 out of 5.0
                 
                 

                Situated near the beach, this villa is 0.4 mi (0.7 km) from Sao Roque Church and 1.5 mi (2.4 km) from Convent of Sao Roque do Pico. Caiado Lagoon is 8.8 mi (14.2 ...

                Pico Dreams - Sportfish

                Pico Dreams - Sportfish

                Rua do Laranjal, 9, Sao Roque do Pico
                  3.0 out of 5.0
                   
                   

                  Situated near the airport, this guesthouse is within a 15-minute walk of Sao Roque Church and Convent of Sao Roque do Pico. Caiado Lagoon and Museu do Vinho ...

                  Casa das Barcas

                  Casa das Barcas

                  Rua Do Cais, Sao Roque do Pico
                    3.0 out of 5.0
                     
                     

                    Situated in Sao Roque do Pico, this bed & breakfast is within 1 mi (2 km) of Convent of Sao Roque do Pico and Sao Roque Church. Mount Pico and Caiado Lagoon ...

                    Aldeia da Fonte Hotel-Apartamentos

                    Aldeia da Fonte Hotel-Apartamentos

                    Caminho Da Fonte Silveira, Lajes do Pico
                      4.0 out of 5.0
                       
                       

                      Situated by the ocean, this eco-friendly hotel is 2.4 mi (3.9 km) from Lajes Whaling Museum and 8.9 mi (14.4 km) from Caiado Lagoon. Convent of Sao Roque do ...