Azores | Lisbon | the Algarve | Gibraltar
Fall 2019 | Oct 23rd to Nov 3rd
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1,061 nm
Oct 23rd 2019
Nov 3rd 2019
Ocean Passage
Coastal Cruising
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This one’s a lot of fun because it combines a nice ocean passage, with some beautiful coastal cruising, a world-class city, and some iconic sailing landmarks.


The trip begins in Ponta Delgada in the Azores, and it should be a quick maybe 3 (to 4) day passage from the Azores over to Lisbon, Portugal. From Lisbon, we then head south along the coast to the Algarve and the magnificent Sagres Cliffs.


If we’ve made good passage time from the Azores, after the Sagres Cliffs, we’ll head over to Lagos/Alvor or a little further East to Ilha de Faro, to enjoy some beautiful barrier islands and a couple of the best kiteboarding locations in Portugal.


Then a sail across the gulf of Cadiz and around to Gibraltar. Passing through the Straits of Gibraltar, see Africa to Starboard and Europe to Port--it feels like you can reach out and touch the two continents.

(Schedule is weather dependent)

Day 1

Joining Day

Arrival times in Ponta Delgada: 12:00 to 20:00 hours. Unpack your bags, relax, meet your fellow crew members, learn your way around the boat.

Day 2 & 3

Preparation & Training

Day two will see us doing briefings and training on Ilha de Sao Miguel. Day three will be preparation and planning for the Ocean Passage.

Day 4 to 6

Azores to Portugal

We will be sailing the Atlantic from Azores to Portugal. This will be a major ocean crossing, covering 780 nm.

Day 7

Arrival, rest, & enjoy the city of Lisbon

According to CN Traveller--Lisbon is Europe's coolest city right now.

Spend the day exploring this jewel of a city on seven hills, (and the evening on-shore if you wish!).

Day 8

Lisbon to the Algarve

Push out early and set sail South along the Portuguese Coast to the famed Algarves and the magnificent Sagres Cliffs. Anchor at dusk at the Sagres Cliffs.

Sagres Cliffs

Day 9

Sagres Cliffs, across the Gulf of Cadiz, to Gibraltar

Wake up and take a morning swim on the beautiful beaches below the cliffs.

Have lunch onboard as we weigh anchor for our overnight passage to Gibraltar. Set watches, raise sails, and head out across the Gulf of Cadiz.


Note:  If we have some extra time, by arriving early on the Azores-Lisbon crossing, we can stop over in Lagoas de Alvor or Ihla do Faro in the Gulf of Cadiz on our way from Sagres to Gibraltar, and enjoy the beautiful barrier islands, beaches, and some of the best kiteboarding grounds in Portugal. 


Here accomplished kite boarders can launch their kites and have a ball, both inshore and offshore, and those that would like to try Kiteboarding can set-up lessons with a local instructor, as there are a number of excellent Kite pro centers along the Algarve.

Faro Barrier Islands

Day 10

The Straight of Gibraltar

Make landfall on Cape Trafalgar—the western end of the Strait of Gibraltar, and see the iconic Rock of Gibraltar appear in the distance as the sun rises.


Passing through the Straits of Gibraltar, see Africa to Starboard and Europe to Port--it feels like you can reach out and touch the two continents.

Gibraltar & North Africa

Day 11

Trip review, clean-up, goodbyes

It’s been an amazing trip—an ocean crossing from the Azores, Lisbon, the Algarve, and Gibraltar. But now it’s time to put the ship back in shape, do our debriefings, and say goodbyes, until the next time.




The schedule above represents a typical itinerary and should only be used as a guide as actual itineraries may change and are always subject to weather and local wind conditions.

All 3rd-party activities, such as scuba diving, kite lessons, and on-shore dining are arranged directly between you and these independent providers.

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