California Meets the Alentejo: Ashley & Jay's Foil Retreat

Some weeks at Time 2 Wing leave a mark — not because everything went according to plan, but because everything just clicked. The waves, the people, the laughs, the dinners that ran way too late. Ashley and Jay's retreat was one of those weeks.

Foilers who've put in the time

Ashley and Jay flew in from California with a serious resume already behind them. This wasn't their first foil trip, not even close. They've chased waves and conditions in different corners of the world, and you can feel it the moment they're on the water — the kind of comfort and reading-the-ocean instincts that only come from putting in real time.

Coaching foilers at this level is a different kind of fun. You're not teaching the basics; you're sharing waves, swapping notes, pushing each other to commit to the bigger sets. And honestly? Watching a couple who both rip is one of the best things about this job.

The conditions delivered. Hard.

We've had good weeks. We've had great weeks. This one was mega.

The Alentejo coast lined up almost exactly the way you'd draw it up — clean swell, manageable wind, the kind of glassy faces where you actually have time to look down the line and pick your section. Day after day, the ocean kept giving. Ashley and Jay made the most of every single session, riding waves that I think they'll still be talking about back in California.

The jetski sessions in particular were something else. You know those moments where you're towing into a set and you can already tell from the lineup that something special is coming? We had a lot of those. Whoops, hollers, the occasional speechless paddle back to the ski. Just intense, properly good times out there.

The evenings (and the drinks, let's be honest)

Here's the thing nobody tells you about hosting people who already know how to foil: the dinners get better. There's no early-night-recovery pressure, no "we need to be sharp tomorrow" caution. Just two foilers from California, the Time 2 Wing crew, and a string of evenings in Vila Nova de Milfontes that ran a little longer — and a little louder — than we'd planned.

Maybe a few too many bottles of wine got opened. Maybe some of those nights ended later than was strictly wise. We regret nothing. The food was unreal, the company was even better, and somewhere in the middle of all that the kind of friendship formed that you can't really plan for — it just happens when the right people end up around the same table.

Until the next chapter

Ashley, Jay — you two were the absolute best to have here. The level of foiling, the energy you brought to the evenings, the way you fit right in with the crew from day one. This wasn't really a retreat anymore by the end of the week; it was just friends hanging out on the Alentejo coast, with some world-class foiling in between.

California is a long flight from Portugal. We don't care. Come back. We'll have the jetski warmed up, a table booked in Milfontes, and probably one bottle of wine too many waiting.

Looking to book your own Foil Retreat on the Alentejo coast? Reach out via time2wing.com — whether it's your first foil trip or your tenth, we'd love to have you.

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