Eighteen boats, fifteen of them monohulls, on three islands in the middle of the Atlantic — and the first decision is which island you fly to, because it determines everything else.
Eight are at Ponta Delgada on São Miguel, in the eastern group. Six are at Horta on Faial and four at Angra on Terceira, both in the central group. São Miguel and Faial are about 150 nautical miles apart across open ocean, so a week that takes in both is a week of passages. An Azorean island-hopping holiday really means the central group, and that is the reason to choose Horta.
The central group is the one place here where the islands are close enough together to work properly: Faial, Pico and São Jorge sit within roughly twenty miles of each other, with the Pico channel between the first two and the great volcanic cone of Pico — Portugal's highest point at 2,351 metres — standing over the whole week. Horta itself is one of the most storied harbours in sailing: the Atlantic crossing's traditional halfway stop, with Peter Café Sport on the front and the marina walls painted by decades of passing crews, each boat leaving its mark.
This is genuine mid-Atlantic sailing. The swell arrives from systems thousands of miles away, the weather changes faster than in the Mediterranean, and the channels between the islands funnel the wind. The Azores high is named after this place for a reason — but when it moves, the Atlantic reaches you. Portugal's country page notes that the Azores carry an additional requirement beyond the mainland rules; check it before booking.
The season is short and the fleet is old by our standards — a 2011 average build year — which fits a market where boats work hard in demanding conditions. Rates sit in a narrow band of €3,300 to €5,970, and all 18 boats change over on a Saturday.
