Current Weather in Velas, São Jorge15°C • 11 kn • SSWLive Forecast
Sailing Itinerary

7-day Azores sailing itinerary from Velas to Horta

7 days 146 nm 4 destinations May–September Moderate EUR 3,400–45,000
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Interactive Route Map

Explore your sailing route. Click on any location to see each stop. You can find detailed information on each day of the itinerary below with insider tips, recommended restaurants, drone spots, activities, and more.

Complete Itinerary

Detailed day-by-day guide with insider tips, ratings, and everything you need to know.

Day 1

Day 1 — Horta (Faial) to Velas (São Jorge)

Velas, São Jorge22 nm4.5 h
Cliff-backed harbor and fajas

Depart Horta for a short blue-water hop to Velas, a natural harbor tucked beneath 200 m cliffs. Settle into the marina, then stretch your legs along the waterfront or plan a hike to nearby fajas and natural pools.

Restaurants
4.0
Water Sports
4.0
Activities
3.0
Sightseeing
5.0
Day 2

Day 2 — Velas (São Jorge) to Angra do Heroísmo (Terceira)

Angra do Heroísmo, Terceira49 nm9.5 h
UNESCO harbor and Monte Brasil

Make an early start for the passage to Terceira, with good chances of spotting dolphins and, in season, whales. Berth in Angra’s sheltered marina and wander the UNESCO-listed old town under Monte Brasil.

Restaurants
5.0
Water Sports
3.0
Activities
3.0
Sightseeing
5.0
Day 3

Day 3 — Explore Terceira (Angra do Heroísmo)

Terceira (shore day)
UNESCO streets, lava tubes, and viewpoints

Stay berthed in Angra for a full island day. Head inland to volcanic features and sweeping viewpoints, then cool off in natural pools before dinner back in the UNESCO town.

Restaurants
4.0
Water Sports
3.0
Activities
2.0
Sightseeing
5.0
Day 4

Day 4 — Angra do Heroísmo (Terceira) to Lajes do Pico (Pico)

Lajes do Pico, Pico54 nm10.5 h
South-coast landfall and whaling heritage

Sail a rewarding blue-water leg to Pico’s rugged south coast. Enter Lajes do Pico, once a whaling base and now home to insightful museums and a scenic waterfront.

Restaurants
4.0
Water Sports
3.0
Activities
3.0
Sightseeing
5.0
Day 5

Day 5 — Explore Pico Island

Pico (shore day)
Vineyards, lava tubes, and lagoons

Dedicate a full day to Pico’s UNESCO vineyard landscapes, volcanic caves, and clear lagoons. Balance gentle hikes with tastings and a swim in natural pools.

Restaurants
5.0
Water Sports
3.0
Activities
3.0
Sightseeing
5.0
Day 6

Day 6 — Lajes do Pico (Pico) to Horta (Faial)

Horta, Faial21 nm4 h
Classic Atlantic port and volcanic vistas

Cross the channel to Faial and berth in storied Horta. Celebrate landfall, then plan time for the island’s Caldeira rim and Capelinhos Volcano landscapes.

Restaurants
5.0
Water Sports
4.0
Activities
3.0
Sightseeing
5.0
Day 7

Day 7 — Explore Faial (Horta)

Faial (shore day)
Caldeira rim, Capelinhos, and Porto Pim

Spend your final day exploring Faial’s volcanic landmarks and beaches. Return to Horta for a relaxed evening before departure.

Restaurants
4.0
Water Sports
3.0
Activities
3.0
Sightseeing
5.0

7-day Azores sailing itinerary from Velas to Horta

Set a course across the heart of the Azores on a 7-day itinerary connecting Faial, São Jorge, Terceira, and Pico. Begin among Horta’s ocean-crossing murals, reach the fajas beneath São Jorge’s towering cliffs, explore Angra do Heroísmo’s UNESCO-listed streets and volcanic interiors, then cross to Pico for vineyards, lagoons, and whaling heritage before returning to Faial’s crater and ash fields. Expect blue-water passages with wildlife sightings, sheltered marinas at key ports, and unforgettable island landscapes.

Why you’ll love it
– Open-water day sails between islands with regular dolphin and whale encounters in season
– São Jorge’s famed fajas and natural pools, perfect for hikes and swims
– Angra do Heroísmo’s UNESCO center, Monte Brasil, and nearby lava caves
– Pico’s vineyard culture, Mount Pico backdrop, and whaling museums
– Faial’s Caldeira rim and Capelinhos Volcano for classic Azorean vistas

Good to know
– Best season May–September for steadier weather and warmer water; still prepare for Atlantic swell and changeable winds
– Visitor berths and essential services are available in Velas, Angra do Heroísmo, Lajes do Pico, and Horta; book ahead in peak months
– Plan early departures for the longer legs (Velas–Terceira and Terceira–Pico) and monitor forecasts and Notices to Mariners
– Respect protected areas at fajas, Monte da Guia, and Capelinhos; follow local signage and drone regulations

This route balances active sailing days with two shore-focused days to explore Terceira and Pico at a relaxed pace. It suits confident crews comfortable with passage planning, variable winds, and occasional swell.