The return leg from the Canaries to the Azores is one of those passages that sorts out who you really are as a sailor. You've likely come down the Atlantic on the trades — fast, downwind, gloriously predictable — and now you're heading back north, roughly 900 nautical miles, beating or close-reaching against the residual northerlies until the Azores High does you a favour and swings the breeze.
Timing is everything here. Leave too early and the high sits stubborn and low, pushing you hard on the wind for days. Leave in May or June and you'll often find a generous arc of westerlies or a brief lull that lets the boat breathe.
The passage itself is rarely dull. Sperm whales appear with unnerving nonchalance in the deep water south of Faial, and common dolphins will work your bow in numbers that make experienced hands stop what they're doing. Nights are long and luminous — the Milky Way reflected in a genuinely dark ocean is something you carry home in your chest for years.
Expect variable conditions: a couple of days of lumpy four-metre Atlantic swell is not unusual, and anyone prone to seasickness should prepare accordingly.
Making landfall at Horta on Faial is one of the great Atlantic arrivals. The marina wall paintings are a tradition you add to yourself if you've crossed from the Americas, and Peter's Café Sport remains the unofficial clearing house for Atlantic gossip and SSCA bulletins. Provision well in Las Palmas de Gran Canaria before departing — Horta's supermarkets are adequate but not generous.
Most bluewater sailors do this on passage aboard their own boats; chartering is limited and skippered options are the practical choice for those without offshore experience.
April through June suits confident bluewater sailors with sea-passage miles; fair-weather coastal cruisers should wait for a settled forecast window or reconsider entirely.