The Azores stopover: nine islands, one decision

The Azores sit in the middle of the North Atlantic — 1,400 nm from Lisbon, 2,000 nm from New York — and every year thousands of sailors pass through them on the way to or from Europe. Most stop at Horta on Faial, paint their boat’s badge on the harbour wall, and leave. A few stay longer. Those are the sailors who understand what the Azores actually are.

Horta: the obvious choice

Horta Marina on Faial is one of the most famous waypoints in the world. The wall outside the marina is covered in hundreds of boat paintings — a tradition that supposedly brings good luck on the onward passage. The marina is well-run, well-stocked, and has good repair facilities. Peter’s Café Sport, where every transatlantic sailor has had a beer, is real and good.

The downside: Horta is crowded from May to September. The marina takes reservations but often has a waiting list. The town is oriented around the sailing traffic in a way that can feel a little transactional.

Flores: the one they miss

Flores is the westernmost island in the EU and one of the most dramatic pieces of land in the Atlantic. Caldeira Funda, a caldera lake ringed by hydrangeas and basalt cliffs, is the most photogenic anchorage you will find this side of the Pacific. The island has a small marina at Lajes das Flores that handles cruising boats, and the town is relaxed in the way places are when they are not on the main tourist circuit.

The sailing: Flores sits exposed on the western edge of the archipelago. If you are approaching from the west, it is a natural first stop. If you are heading west, it is the last land you will see before North America.

Pico: the volcano at anchor

The marina at Madalena on Pico is functional. The anchorage in the channel between Pico and Faial is excellent — good holding, sheltered from the prevailing swell, and you wake up with the bulk of Pico’s 2,351m volcano in front of you. The island has good wine and excellent hiking.

The practical question: where to clear customs?

If you are arriving from outside the EU, you clear customs at the first port of entry. Horta is the easiest — customs officers are experienced with yachts and the process is quick. Santa Maria, the southernmost island, is the official entry point by regulation, but Horta is accepted in practice for passage yachts.

How long to stay

If you have time, two weeks in the Azores is not long enough. If you are on a tight passage schedule, three to four days in Horta to rest, provision, and fix whatever broke on the passage is the minimum. The temptation to push straight on is understandable — Horta to Falmouth is 1,300 nm and the weather windows close in October — but the Azores reward the sailor who slows down.

The wall in Horta is not going anywhere. Your boat’s badge will be there next season. The question is whether you saw the islands or just the marina.