Azores to Gibraltar: Sailing Paikea Upwind Across the Atlantic

We left Horta on the island of Faial with about a thousand nautical miles between us and Gibraltar, and we weren’t going to get there in a straight line. The plan was to sail up past Terceira, tuck into the eastern side of a high pressure system, and let the northerlies that build there shoot us across. Getting to that high meant one thing first: going upwind, in a boat that most people will tell you shouldn’t be very good at it.

Leaving Horta

Fourteen knots of true wind, true wind angle sitting around 46 to 50 degrees, apparent wind angle down around 30. That’s wind coming in shallow over the deck, and with the boat’s own six or seven knots added to it, we were seeing 19 to 20 knots of apparent wind up on deck even though it was a mild afternoon by open-ocean standards. Boat speed was sitting around seven knots over the ground, tacking through something close to 90 degrees — a little under it on some tacks.

The number that mattered more than any of that: we caught and passed a 40-foot monohull that had been sailing the same route. We tacked to leeward of it, held a couple of degrees higher, put some distance on, then came back up and sailed straight past. Both boats were bashing upwind in the same breeze; ours just did it faster and pointed higher. Catamarans “can’t go upwind” is one of those lines that’s more folklore than physics, and it’s fun to disprove it against a boat that’s actively trying to do the same thing next to you.

A Rough Night Off São Jorge

Earlier in the passage the breeze had been up in the 20s and we’d dropped to second reef, doing around nine knots upwind through a noticeably lumpier sea state. That’s the trade-off with a light, powerful boat going upwind fast — she punches into the waves rather than riding gently over them, and the wing deck and bow cop the consequences. Green water was coming over the bow and slapping the underside of the wing deck regularly, and by the time we eased back to first reef everything below was salt-crusted: cushions, the door behind the cabin, the steering wheel, all of it.

It was rough enough that appetites suffered. The cat was seasick twice. Our son Olly — who doesn’t normally get seasick at all — went a shade of green that had nothing to do with his apple and was sick once too, then spent the rest of the morning asleep next to the cat, both of them off duty. It happens. Going upwind at speed in 15 to 17 knots of breeze with second reef and jib up is a genuinely different motion to reaching or running, and even seasoned crew can get caught out by it.

Behind São Jorge — a long, skinny, waterfall-lined island that’s worth the detour just to look at — the sea state eased a little as we came into its lee, which gave everyone a chance to reset before the next push.

The Bang

At one point we heard a loud bang from the starboard side and immediately thought the worst: a broken daggerboard, mid-Atlantic, a long way from a boatyard. We got a halyard on it, winched it up to check, and — relief — the board came up intact. Rudder still there, saildrive still there, daggerboard still there. Whatever made the noise, it hadn’t taken anything with it.

Our best guess, once everyone had calmed down: a wave hit one of the wing deck’s step boxes at exactly the wrong angle and made a bang loud enough to sound structural. It’s the kind of noise this boat makes reasonably often when she’s slamming upwind — usually forgettable, occasionally alarming enough to stop everything and go and look.

It also got us talking about how the daggerboard’s sacrificial break point is actually built. There are technically two points on it now: the one Shayne added and extended by 400mm during work in Cartagena, and the original factory one further down. We’re sceptical the factory one was ever a genuine sacrificial point — the laminate runs through it as one continuous piece rather than showing any sign of a deliberately weakened section, which isn’t what you’d expect if it was designed to give way under load rather than let something more expensive break instead.

One New Rudder

The original plan for this refit stage was to have two new rudders built before setting off. Time ran out, so we crossed the Atlantic with one new rudder, one old one, and a genuinely asymmetric setup either side of the boat. It worked — nothing about the crossing suggested the mismatch caused a problem — but it’s not the setup we’d choose if the schedule had cooperated.

If you want the fuller story on why we went from the original 29.8kg stainless rudders down to a 7.5kg carbon build, and the load-path thinking behind it, that’s covered properly on the Rudders page.

Why We Came Back to Spain

The busy month and a half before this crossing wasn’t just about boat prep. Shayne was offered a spot on an America’s Cup team joining the 2024 campaign, which meant a return to Spain was already on the calendar before we’d even left the Caribbean — this passage was always going to end with us back on the peninsula, not just passing through.

In the time we had, we got the chain-plate finished using the same process as the earlier one, made new strops for where the rotating rig’s stays attach at the masthead, and got a new lightweight headsail sorted. It’s not perfect yet — there are improvements we can already see — but the potential is there and we’re happy with where it’s landed for a first version.

None of that would have been possible without the run we’d just had getting to the Azores in the first place. Saint Martin to Horta was pure downwind sailing in near-ideal conditions: 210 nautical mile days at times, an 8 to 9 knot average for the whole crossing, spinnaker up for most of it bar a couple of lighter patches. With 150kg out of the boat since the last major weight pass, she’s noticeably livelier reaching and running than she was — a little rocket ship, by Shayne’s own description.

What’s Next: Orca Alley

The next stretch takes us across what’s become known, only half-jokingly, as Orca Alley — the stretch of water off the Iberian coast where black and white orcas have taken a particular interest in sailboat rudders in recent years. We’d like to keep both of ours, especially the new one. Wish us luck.

In This Series

This is part of a longer story — six chapters covering the return crossing from the Caribbean to Barcelona, ending with the discovery that kicked off Paikea’s biggest refit yet. See the full series on Crossing the Atlantic: Caribbean to Barcelona, or read it in order below: