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 85 Hotels in Pico Island
Aldeia das Adegas

Aldeia das Adegas

Rua das Adegas 3A, Sao Roque do Pico
4.5 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
4.5 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 ...

A Casa do Ouvidor

A Casa do Ouvidor

Estrada Regional, 22, Sao Roque do Pico
4.5 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 ...

Casa do Comendador

Casa do Comendador

Rua de Baixo, No 17 S.Miguel Arcanjo, Sao Roque do Pico
4.5 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
3.5 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
3.5 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 ...

Pico Dreams - Sportfish

Pico Dreams - Sportfish

Rua do Laranjal, 9, Sao Roque do Pico
3.5 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 ...

Aldeia da Fonte Hotel-Apartamentos

Aldeia da Fonte Hotel-Apartamentos

Caminho Da Fonte Silveira, Lajes do Pico
4.5 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 ...

Adegas do Pico

Adegas do Pico

Rua do Ramal, 14, Sao Roque do Pico
4.5 out of 5.0

Located in Prainha, this romantic country house is within 12 mi (20 km) of Sao Roque Church, Convent of Sao Roque do Pico, and Caiado Lagoon. Lajes Whaling Museum ...