The Atlantic Ocean has been crossed by sailors for five hundred years, and the island groups that mark its passages have shaped every offshore route ever since. The Azores sit at the precise midpoint of the North Atlantic, 1,900 miles from Newport and 1,350 from Lisbon — a natural landfall for every transatlantic passage and a mandatory stop for most of them. The Canary Islands anchor the eastern end of the trade wind route to the Caribbean, where the ARC fleet gathers every November and thousands of cruisers spend the winter preparing their boats for the crossing. Bermuda stands alone 635 miles east of Cape Hatteras, the finishing line of the oldest ocean race in American sailing and the waypoint for every US East Coast boat heading south. Cape Verde, 1,300 miles south of the Canaries, sits deep in the reliable trades and offers the shortest ocean crossing to both Brazil and the Caribbean.
These are not casual sailing destinations. All four require offshore passage-making to reach — multi-day ocean crossings in open water, careful weather routing, and boats prepared for conditions that will not be gentle if you choose the wrong window. These guides are written for sailors who are ready for that, and who want practical information about what they will find when they arrive: the marinas, the provisioning, the customs processes, the local sailing culture, and the passages onward.
The Azores: Atlantic Crossroads for Offshore Sailors
Equidistant from the US and Europe, Horta is the mandatory stop for every transatlantic passage — the wall, Peter's Café Sport, and the nine islands that reward the sailor who lingers.
The Canary Islands: The Atlantic's Premier Passage-Making Base
The launching pad for the downwind Atlantic trade wind route to the Caribbean — Las Palmas, the ARC, and why thousands of boats winter here every year.
Bermuda: The Offshore Sailor's Island
The Newport Bermuda Race finishing line, 635 miles east of Cape Hatteras, and the reef-girdled gateway island for the run south to the Caribbean.
Cape Verde: The Last Stop Before the Tropics
Mindelo's spectacular harbor, morna music, and the ideal jumping-off point for sailors heading to Brazil or the Caribbean on deep trade wind reaching.
Planning the Atlantic Circuit
The classic offshore sailing circuit treats these islands as a sequence. Departing from the US East Coast in spring, a boat crosses to Bermuda first — a 635-mile reach that tests crew and equipment. From Bermuda, the options open: continue east to the Azores (1,800 miles), or turn south toward the Caribbean. The classic autumn circuit reverses: down from the Canaries to Cape Verde, then west across the Atlantic on the trade winds to the Caribbean. The Azores are the pivot point of nearly every North Atlantic passage, sitting at the crossroads of the eastbound and westbound routes.
Weather routing is not optional on any of these passages. The North Atlantic is a dynamic ocean. The Azores High is the dominant feature — when it is strong, it drives the trade winds south and creates the calms and gentle conditions that make the westward crossing pleasant. When it weakens or shifts, the depressions that track east along 40–50 degrees north bring gales that can reach any of these islands. The Gulf Stream between the US coast and Bermuda amplifies any weather system that passes over it. Cape Verde sits at the edge of the trade wind belt where easterly winds are reliable but the approach from the Canaries can be an exciting beat. Know your weather before you depart, have a plan B for your departure window, and carry sufficient provisions to wait if the window does not materialize.
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