Azores 7-Day Sailing Itinerary from Faial

Faial - 7 day sailing itinerary

Duration: 7 days
Distance: 147 nm
Difficulty level: Advanced
Best season: May-September
Off Season: October-April
2

Sailing itinerary overview

Set sail on a breathtaking sailing route in the heart of the Azores, from the legendary harbor of Horta to the lush trails of Terceira and the rugged charm of Pico.

Day 1 Faial

Faial

Your sailing trip will start from Horta - a legendary stopover for Atlantic sailors, renowned for its marina, vibrant maritime history, and the iconic Peter Café Sport. Located on Faial Island, it's a place where ocean crossings are celebrated, stories are shared, and hulls are painted with colorful murals on the marina walls — a sailor’s tradition for safe passage. Surrounded by volcanic landscapes and views of majestic Pico Mountain, Horta is both a refuge and a rite of passage for anyone sailing the Azores.

Day 2 São Jorge Island

22 nm 4 hours
São Jorge Island

Velas Marina, nestled beneath towering 200-meter cliffs of São Jorge Island. Explore the charming towns of Velas and Calheta, then cross the island — just 8 km wide but rising steeply to 300 meters — to discover some of its most remarkable fajãs (narrow lava platforms at the base of volcanic cliffs). Don’t miss Cubres, Ouvidor, and especially Fajã de Santo Cristo — a unique, ring-shaped natural lagoon that’s fast becoming a sanctuary for surfers.

Day 3 Terceira Island

49 nm 10 hours
Terceira Island

Enjoy a day of sailing to Terceira Island - Angra do Heroísmo. Keep an eye out — with a bit of luck, you might spot playful dolphins, turtles, or even whales.

Day 4 Explore Terceira Island

Explore Terceira Island

Terceira Island offers a perfect blend of natural beauty and cultural richness. Angra do Heroísmo, is its crown jewel, with elegant architecture, cobbled streets, and a proud maritime past. Beyond the city, Terceira’s lush green landscapes hide volcanic caves like Algar do Carvão and dramatic coastal views. Known for its festive spirit, traditional bullfights, and warm hospitality, Terceira is a lively and unforgettable stop for sailors exploring the Azores.

Day 5 Pico island

55 nm 10 hours
Pico island

Set sail for Pico Island and enjoy another full day on the water. Take in the raw beauty of Pico’s rugged south coast before arriving in Lajes do Pico — the birthplace of the Azores’ once-legendary whaling industry.

Day 6 Explore Pico Island

Explore Pico Island

Pico Island deserves at least a full day to explore. Start in Lajes do Pico, the heart of the island’s historic whaling culture, by visiting the Whalemen’s Museum. Then, continue to the Vineyard Landscape of Pico Island — a unique patchwork of lava stone walls and vines found nowhere else in the world. In São Roque do Pico, discover the fascinating Whaling Industry Museum. Finish your loop inland, passing the peaceful highland lagoons of Capitão and Caiado on your way back to Lajes.

Day 7 Horta - Faial

21 nm 4 hours
Horta - Faial

Arrive at Horta Marina and enjoy a well-earned final night on board — and don’t miss the chance to toast your week of sailing with a legendary gin at Peter’s Café Sport. But remember, Faial is more than just yachts, the marina, and the town of Horta. Before you leave, take time to admire the impressive Caldeira Volcano, a vast crater measuring 2,000 by 400 meters, and visit the Capelinhos Volcano — a surreal, lunar-like landscape of 3 square kilometers, born from over 300 eruptions and earthquakes in 1957.

Optional Stops Along the Route

Marina Horta

Marina Horta

Marina

Horta marina enjoys legendary status among ocean sailors and is seen as a must-stop transatlantic port. While some note arrival hassles, the marina’s convivial atmosphere and Horta’s unique charm make it well regarded by sailors.

Information provided by Navily.com
Horta

Horta

Anchorage

The general atmosphere is lively and friendly, with the famous Peter Café and waterfront spots being highlights. Shoreside facilities are comprehensive—including bars, restaurants, grocery stores, bakeries, chandlers, and laundromats. Access from the anchorage to town is easy, by dinghy or on foot.

Information provided by Navily.com
Caldeira Do Inferno

Caldeira Do Inferno

Anchorage

A well-sheltered anchorage popular with flotillas passing through the channel. The village has a good supermarket and a few waterfront tavernas serving fresh fish. Fuel and water are available at the quay. Expect company in high season — arrive early to secure a stern-to berth.

Information provided by Navily.com
Madalena

Madalena

Anchorage

The Ermoúpoli marina in Syros is liked for its central location and charming town, with many shops, restaurants, and a vibrant atmosphere. While the lively setting is a major draw, the frequent and strong swell from ferries poses a significant recurring problem for mooring and comfort. Despite this, sailors generally consider it worth the stop due to the local vibe, reasonable prices, and easy access to island amenities.

Information provided by Navily.com
Marina das Velas

Marina das Velas

Marina

The general impression of Marina Velas is. Sailors generally highlight the warm welcome, safety, and the friendliness of the small town. While the marina is small and berths for larger boats are limited, the experience offers peaceful atmosphere, cleanliness, professionalism, and the genuine pleasure of visiting an authentic port.

Information provided by Navily.com
Velas Port Commercial

Velas Port Commercial

Anchorage

Sailors generally view this bay as an enjoyable anchorage, surrounded by green cliffs and close to a charming small village with useful amenities. The island also offers natural beauty, hiking opportunities, and local dairy specialties.

Information provided by Navily.com
Marina d'Angra

Marina d'Angra

Marina

Sailors appreciate the lively city, beautiful setting, and good harbor protection, with occasional advice to reinforce moorings under certain winds. Sailors value easy access, a broad range of essential services, and enjoyable walks and excursions in town and around the island. The warm welcome further enhances the experience.

Information provided by Navily.com
Baixa da Prainha

Baixa da Prainha

Anchorage

General feedback for the anchorage is good: Sailors appreciate the beautiful surroundings, with Angra lauded as one of the Azores' nicest towns. The area is lively, welcoming, and offers various activities and walks, though some find it somewhat touristy at times. The location balances scenic value and shore convenience, making for an enjoyable anchoring experience.

Information provided by Navily.com
Forte de São João Baptista

Forte de São João Baptista

Anchorage

A well-sheltered anchorage popular with flotillas passing through the channel. The village has a good supermarket and a few waterfront tavernas serving fresh fish. Fuel and water are available at the quay. Expect company in high season — arrive early to secure a stern-to berth.

Information provided by Navily.com
Ilhéus das Cabras

Ilhéus das Cabras

Anchorage

The Ermoúpoli marina in Syros is liked for its central location and charming town, with many shops, restaurants, and a vibrant atmosphere. While the lively setting is a major draw, the frequent and strong swell from ferries poses a significant recurring problem for mooring and comfort. Despite this, sailors generally consider it worth the stop due to the local vibe, reasonable prices, and easy access to island amenities.

Information provided by Navily.com
Marina Lajes Do Pico

Marina Lajes Do Pico

Marina

Sailors show that the marina offers a friendly atmosphere and unique charm. Despite its small size and limited berths, it stands out for its tranquility, closeness to nature, and the outstanding welcome given to Sailors. Many strongly suggest stopping here, even though advance reservation is needed.

Information provided by Navily.com
Lajes

Lajes

Anchorage

A well-sheltered anchorage popular with flotillas passing through the channel. The village has a good supermarket and a few waterfront tavernas serving fresh fish. Fuel and water are available at the quay. Expect company in high season — arrive early to secure a stern-to berth.

Information provided by Navily.com
Ribeiras Anchor

Ribeiras Anchor

Anchorage

The Ermoúpoli marina in Syros is liked for its central location and charming town, with many shops, restaurants, and a vibrant atmosphere. While the lively setting is a major draw, the frequent and strong swell from ferries poses a significant recurring problem for mooring and comfort. Despite this, sailors generally consider it worth the stop due to the local vibe, reasonable prices, and easy access to island amenities.

Information provided by Navily.com

Share your thoughts & ideas about sailing from Faial

We’d love to hear your comments and suggestions! Share with fellow sailors recommended marinas or coordinates of anchorages to stay for the night or even your favorite restaurant, winery or oyster farm.

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