Portugal Sailing Itineraries

Azores: 2 Weeks Sailing Trip

Sailing around the Azores has so much to offer. Here is an itinerary for 2 weeks sailing holiday between the central & western group of islands. Just copy and paste to your agenda, pack your suitcase, book a boat, and take photos to remember the holiday of your lifetime. If you like a sailing holiday for one week check our one week trip.

Day 1: Sail to Flores Island, 138 miles

Flores Island

Sailing across the Atlantic directly to Flores is a tremendous opportunity to enjoy and feel the ocean. You will run the risk of watching a variety of dolphins and other species of cetaceans.

Day 2: Arrive at Lajes das Flores (Floress Island)

The island of Flores is Nature in all its exuberance. It is an occasion to observe the coastal caves, waterfalls and the impressive valleys. Lajes das Flores is a cozy refuge picturesque town and fishing port, surrounded by green fields. Flores was declared a Biosphere Reserve in 2009 by the UNESCO due to its landscape, geological, environmental and cultural features.

Day 3: Visit Flores Island

Discover the enchanting towns of Lajes and Santa Cruz and their natural beauties. Going around the island, you may visit one of the most famous natural monuments of the Azores, the rock Rocha dos Bordoes is made up of a large set of vertical basalt columns. After that, visit the Fajãzinha, a typical village by the sea with picturesque ruins of water milk where you can appreciate the Ribeira Grande waterfall. Take a beautiful bath next to the black rocks at the Poço do Bacalhau, a natural swimming pool and visit the enormous cavern of Gruta dos Enxareús.

Must visit: Gruta dos Enxareús; Miradouro da Rocha do Touro; Rocha dos Bordõe and  Cascata do Poço do Bacalhau.

Days 4/5: Round Corvo Island and sail to Lajes do Pico (Pico Island), 153 miles

View of Corvo Island from above

Enjoy another full day of sailing and admire the natural beauty of Pico’s rough south coast before entering the birthplace of the Azores once legendary whale industry, Lajes do Pico. Start visiting Pico Island from the heart of its ancient whaling culture, visiting the Whalemen’s Museum at Lajes do Pico.

Must visit: Whalemen’s Museum at Lajes do Pico.

Day 6: Visit Pico Island

Organize yourself. One day to visit Pico is the least you can do. Start contouring the Island along its coastline towards the unique Landscape of the Pico Island Vineyard Culture, a UNESCO World Heritage Site. Continue through the coastline, and you will be amazed by the roughness of its magma setting. Once in São Roque do Pico visit the Whaling Industry Museum and start climbing the mountain back to Lajes do Pico, stopping at the altitude lagoons of Capitão and Caiado.

Must visit: Landscape of the Pico Island Vineyard Culture; Whaling Industry Museum at São Roque do Pico; Capitão and Caiado Lagoons.

Day 7: Sail to Angra do Heroismo (Terceira Island), 54 miles

Welcome to another full day of sailing and cross your fingers for an amazing ride shared with, for sure dolphins and perhaps turtles and whales! You won’t be the first lucky one.

Day 8: Visit Terceira Island

Terceira Island

Once in Angra do Heroismo, get yourself lost in the immaculate and well-preserved streets of one of the most historical cities of Portugal and a UNESCO World Heritage site. Still, Terceira does not end in the unique charm of Angra. You must drive along the green leaves of a truly stunning landscape towards Algar do Carvão, with its magnificent stalagmites, stalactites, and lake. And by the way, Terceira is the land of joy and excitement in the Azores.

Must visit: UNESCO city of Angra do Heroismo; Algar do Carvão caves.

Day 9: Sail to Praida da Graciosa (Gracious Island), 45 miles

Another sailing day, another opportunity to observe and enjoy the presence of natural treasures like dolphins, turtles and, luckily, whales. Gracious is well-known for its hospitality and traditions.

Day 10: Visit Gracious Island

Classified by UNESCO as a Biosphere Reserve, the island of Gracious is the second smallest of the archipelago and is ranked as an exceptional location for diving and fishing. The charming town of Santa Cruz with its typical windmills provides a single glance. Calder da Graciosa and Furna do Enxofre, a beautiful volcanic cave, are the most iconic natural attractions of the island. The well famous thermal water of Carapace invites you to a therapeutic bath.

Must visit: Town of Santa Cruz; Caldeira da Graciosa; Furna do Enxofre.

Day 11: Sail to Velas (São Jorge Island), 38 Miles

Velas (São Jorge Island)

Your last full sailing day, served along the marvelous North coast of S.Jorge Island, with its indented coastline shape, full of contrast between the central ridge which crosses the island lengthwise and the sharp and rocky coast, with its steep cliffs, which turns the landscape into a mixture of aggressiveness and serene beauty. When arriving at Velas Marina, witness its unique natural scenery, surrounded by a cliff with 200m high.

Day 12: Visit São Jorge Island

Start discovering São Jorge Island. You could first visit the town of Calheta. Across the thin (8 km) but steep Island (300 m) to visit some of its more fabulous rajas (low tongues of lava at the bottom of steep volcanic cliffs). Don’t forget Cubres, Ouvidor and, especially, Santo Cristo, a unique natural lagoon ring-shaped, that is now becoming a surfing sanctuary.

Must visit: Town of Calheto; Faja dos Cubres, Fajã do Ouvidor, and Fajã de Santo Cristo.

Day 13: Sail back to Horta (Faial Island), 22 miles

Arrive at Horta Marina and get yourself a well-deserved last night on board, along with a mythical Gin at Peter’s Café Sport to celebrate a full week of sailing while traveling and discovering the wonderful Azores. But don’t forget, Faial is not only about yachts, the Marina and Horta. Don’t leave us before admiring the Caldeira Volcano, a deep crater of 2000 x 400 meters and Capelinhos Volcano, an almost lunar and arid landscape of 3 square km conquered to the sea by more than 300 explosions and earthquakes in 1957.

Must visit: Caldeira and Papelinhos Volcanos.