Leaving Horta on Faial after the obligatory marina wall painting is one of those departure moments you carry for years. The passage east to Cascais or the Tagus runs roughly 1,500 kilometres across deep North Atlantic water, and it demands respect rather than romance. The Azores High sits between you and home, which means this is rarely a downwind sleigh ride.
Most boats work a two-step: head north first to around 42–44°N until you find the westerlies properly established, then gybe east and let the gradient carry you in. Try to punch straight east from Faial and you'll spend days flogging into a light headwind while your fuel tanks quietly empty.
Day to day, the passage swings between glorious reaching in 20 knots of west-southwest breeze and grey, lumpy patches as Atlantic lows track through. Dolphins are a near-daily certainty; sperm and blue whales appear with real frequency in the first few hundred miles east of the archipelago, which stays with you long after the seasickness fades.
Night watches here feel genuinely offshore — dense darkness, bioluminescence in the wake, no shipping lanes crowding you.
Cascais makes a satisfying landfall with its wide bay, reliable anchoring east of the marina, and good chandlery for anything that broke mid-passage. From there it is a short, current-assisted motor or sail up the Tagus into Lisbon's Doca de Alcântara, where cold Vinho Verde and a pastel de nata taste entirely disproportionately good after nine or ten days at sea.
This is an offshore delivery or experienced cruiser's passage, not a chartering holiday — leave Horta between late May and early July before the Atlantic season advances.