Men's Journal

Illustration by James Noel Smith Photo credit: Bob Smiley

VIRGIN GORDA

Stage Your Own Regatta

Bitter End Yacht Club sits on Virgin Gorda’s North Sound, among the most secluded and protected deep-water harbors in the Caribbean — making it a great venue for an impromptu regatta on a rented 13-foot Laser. I found this out nine years ago while on a 10-day chartered trip through the Caribbean with William F. Buckley, the late, great father of modern conservatism.

Bitter End hosts amateur regattas every Sunday and Wednesday afternoon, but if you’ve got a quorum of willing partners like we did, you can set up your own private race around the eight-mile sound anytime, using whatever you can find to create a makeshift course. Buckley used two buoys and our anchored yacht to map out a triangular route. I’m not a sailor by any definition (luckily, Bitter End doesn’t ask for any proof of expertise), but I found myself paired with an architect who had spent his fair share of time on Long Island Sound. Buckley (76 years old at the time) was paired with a 30-something friend who hadn’t lifted a finger all week and whose full-time job was raising capital to colonize Mars. To put it bluntly: I liked our chances.

Our German captain, Franz, blew the yacht’s horn, and off we went. Buckley’s skiff took the lead and never lost it. He never missed a buoy, never broke a sweat, and never lost the powder-blue skipper’s cap he’d worn all week. This was, after all, the same man who in younger days sailed across the Atlantic. And the Pacific. My partner and I stayed busy capsizing and getting whacked by the boom. It was the perfect place to try sailing, even if we did end up getting schooled by an American icon.
— Bob Smiley

TK

Illustration by James Noel Smith

Trip Planner (click on the map at left for a larger view)

Hiring a Boat: Bitter End Yacht Club still rents the same 13-foot Lasers that Buckley took for a sail (and the staff still remembers the day he came in). Rentals are available year-round, but the best winds are winter and spring (from $40 an hour; beyc.com).

Beyond Sailing: The island’s Baths — a maze of pools and grottoes amid 40-foot granite boulders strewn across a white-sand beach — are often overrun with tourists by midmorning, so visit the adjacent Spring Bay National Park. It’s got an even bigger beach and more remote granite formations to explore (bvinationalparkstrust.org). The North Sound is also home to a series of small tropical islands, but you can find the best views underwater while snorkeling at ———————————————the majestic Eustatia Reef (from $30; divebvi.com).

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