Sailing Directions by Don Street
A passage across the Atlantic Ocean is not a trip to be lightly undertaken. Your boat and crew must be prepared to face heavy weather. If this will be the first ocean passage for you or your boat, do some rehearsals: While still in your home waters, when a good hard blow comes through, take your boat out for a sail and ascertain any deficiencies in either boat or crew. Take your boat back in and rectify the deficiencies. Then go out in a second blow, which you will be much better prepared for. Go home again and rectify any deficiencies that are still not corrected from the first trial. Etcetera.
The hardest part of sailing westward across the Atlantic is getting from Europe to the Canaries or Madeira. Once there it is basically all down hill and easy sailing to the Caribbean.
Take a look at the weather charts on the back of the Imray-Iolaire North Atlantic Passage Chart 100. These will show why you should have gotten out of Northern Europe by September, as the gale frequencies there increase drastically after midSeptember, through October and November. By now, you should be in Madeira or the Canaries, or even the Cape Verde Islands.
If you are leaving from Gibraltar, you should carefully check your weather report — in November you can run into some bad southwest blows, and the northwest coast of Africa has virtually no harbours of refuge. Take off on a good weather report from Gibraltar, and work your way well to the west to give yourself plenty of sea room before heading southwestward to Madeira or the Canaries.
Madeira and the Canaries
In the Madeiran Archipelago island of Porto Santo, there may be room in the harbour at the marina, or you can anchor off.
In Madeira one can find a wonderful secluded anchorage in Bahia de Abra. It is absolutely deserted, and a few miles west of there, one can find the Quinta do Lorde marina three miles east of Canical.
If you continue on to the Canaries you will discover that there are relatively few anchorages and the marinas are chock-a-block full. Unless you are joining the rally, forget about going to Las Palmas, Gran Canaria, until after the ARC 2009 departs on November 22nd. There is a marina at Rubicon on Lanzarote, plus Puerto Calera where space might be available.
The islands’ best infrastructure to support the yachting industry and make good any deficiencies discovered in gear and equipment is in Tenerife. In the opinion of many, the nicest islands in the Canaries are the three westernmost islands: Palma, Hiero and Gomera.

The Cape Verdes
We visited the Cape Verdes on Iolaire in 1985 and 1989 and preferred them to the Canaries. I revisited them via “the big bird” in 2002, and again in 2005 on Sincerity, an 88-foot ketch.
I recommend spending December exploring the Cape Verdes, and crossing the Atlantic in January when the trades have filled in and late-season hurricanes are avoided. Landfall should be Isle Sal to check in, then sail downwind to São Nicolau, Sta. Luzia (an uninhabited island with a three-mile-long white sand beach), and São Vicente and its port city of Mindelo.
Mindelo is wonderful, with beautiful colonial Portuguese architecture. A German, Kai Brossman, has completed a 120-berth marina with repair services, electronics, rigging and sail repair. Kai also points out the Cape Verdeans are wonderful at improvisation; he feels that within three weeks anything broken on a yacht can be replaced or repaired.
After Mindelo, sail south to Santiago, which has a dozen unexplored anchorages available to the experienced sailor — check Google Earth and see what I mean. Then visit Fogo, with its colony of blue-eyed, red-haired Cape Verdeans descended from a French count who arrived in the 1880s and cultivated grapes (and the local damsels!). Then on to Brava, which has an excellent harbor on the northeast side and a sheltered cove on the southwest corner, a perfect jumping-off spot to cross the Atlantic.
Across the Pond
I am strongly of the opinion that when crossing the Atlantic you should go from the Canaries down to the Cape Verdes, enjoy the cruising there, and then cross from the Cape Verdes to the Eastern Caribbean. The reason I say this is because the Great Circle route from the Canaries is 2,535 miles, but this route can really only be sailed by boats that have plenty of fuel and/or are lightweight fliers with a crew that is willing to do a lot of sail changing, setting spinnakers and the like. The more traditional route is to head southwest from the Canaries, at least down to 20°N, and then across — about 2,615 miles. This route brings you quite close to the Cape Verdes,
so why not sail from the Canaries to the Cape Verdes? It is only 780 miles, with guaranteed Trades down the African coast.
You can enjoy the Cape Verdes and then take off from Brava, a wonderful little island where the Yankee whalers used to pick up crew. From there to Antigua (2,175 miles) you are down in the deep Trades, and will have some glorious sailing as the course is a little bit north of west and the Trades are a little bit north of east. You can rig your spinnaker pole semi-permanently out to starboard, to be used to wing out the jib if it is blowing hard, or for your spinnaker if the wind goes light. Iolaire, 46 feet on deck, has sailed three times from the Cape Verdes to the islands
of the Eastern Caribbean — in 14 days and some hours in 1949, under gaff rig when owned by
R.H. “Bobby” Sommerset; then in 1985 and 1989 under my command as a double-headsail
Marconi yawl. On all three trips the spinnaker pole was rigged to starboard and left up there for
the entire trip. No gybing!
Southwest Winds
If you look at the weather charts, you will note that in November in the Canaries, there is a
southwest arrow. If the wind goes round to the southwest, you should sit in the Canaries and
wait until it goes back around to the easterly quadrant. It can blow southwest for two or three
days and blow hard. The ARC has discovered this occasionally, when participants were discouraged to discover they were beating to windward in heavy weather for the first three or four days of their transatlantic crossing, rather than having a glorious sleigh ride all the way.
It should be noted that a southwester could settle in for even longer periods. In 2002 dozens of
boats that left the Canaries were driven all the way down to the Cape Verdes, where they stopped to pick up fuel and/or wait for the wind to go around to the east.
Boat preparation and sailing directions westward across the Atlantic will be covered in more detail in my completely new Street’s Guide to the Atlantic and Caribbean Basin, available in 2010. A detailed guide to the Cape Verdes will form an entire chapter. I recommend the following charts for a westward transatlantic crossing:
- Imray C20: Gibraltar to Azores and Canaries
- Imray-Iolaire E2: Islas Canarias. Plans: Pto de la Luz, Pto de los Marmoles and Pto de Naos, Pto de San Sebastian, Pto de Santa Cruz, Darsena Pesquera (Santa Cruz de Tenerife), Morro Jable, Pto de la Estaca
- Imray-Iolaire E3: Arquipelago da Madeira. Plans: Pto Santo, Pto do Funchal
- Imray-Iolaire E4: Arquipelago de Cabo Verde. Plans: Pto da Furna, Pto Grande, Pto de Sal-Rei, Pto Novo, Pto da Praia, Cavaleiras, Pto Velho, Bahia da Palmeira
This article originally appeared in the November 2009 issue of Carbbean Compass.