Photo: Alton Bertie Photography
The name is really a quiet promise. Windward is the direction you sail on purpose — into the wind, not just running with it. Reserve is the rest: reserved, in the old-fashioned sense. More interested in getting it right than talking about it.
Photo: Alton Bertie Photography
The Adventure and The Second Wind are kept to the same standard — well-maintained, easy to relax on, and crewed by people who actually know these waters. We'd rather do two boats well than a fleet of ten adequately.
Windward Reserve maintains a small, trusted roster of local captains — and chefs, if you'd add one — rather than staffing up big and hoping for the best. You'll get someone who's sailed these waters long enough to have opinions about them, not just directions to them. Every trip is fully captained; we don't offer self-captained charters.
Anyone can point you to The Baths. Fewer people can tell you it's worth going before 9am, or that the Bubbly Pool only bubbles when there's a north swell running. That kind of detail is the whole reason the Locations page is built the way it is — around the kind of day you want, not just a list of famous names.
Take a look at the fleet, or jump straight to checking available dates.