Friend trips, well-fed.
The Drake Supper Club is the un-commercial side of SailChecker. Every year or so we charter a yacht somewhere we want to sail, fill it with friends, and run a trip the way we’d want to be hosted. Good food. Better wine. A route that earns its swim stops.
Spare berths get offered to SailChecker members at a real discount. The trade is simple: you give us honest feedback, model for the (low-key) filming crew when we ask, and write a review when you’re home. That’s the whole deal.
…stunning natural beauty, exquisite food and wine, watersports — and best of all, great company.
Two logged. One open. Two on their way.
The trip that gave us most of the photos — and the lesson that monohulls beat cats under sail. Birra Messina, charcuterie in Lipari boats, Nina the Piaggio Ape.
See how it went → Logged · Oct 2025Seven days, six islands, one Oceanis 46.1. Hydra, Kythnos hot springs, Sounion at sunset. Fancy dress night returned, predictably.
See how it went → Active · Oct 2026Early October, exact week TBC. Eight cabins around a Sun Odyssey 440, Stromboli at sunset, granita for breakfast.
Reserve a cabin → Coming · ’27 (TBC)All genders welcome — excluding men. 🙂 Same Drake shape, a different set of voices around the table. Pitched as a training week: hands on the helm, lines in your hands, MOB drills. Date locks when the cabins fill.
Register your interest → Coming · 2027Trade-wind sailing through the British Virgin Islands. Drake’s Anchorage (yes, really), Foxy’s, Anegada lobster.
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