If not all who wander are lost, then not all who charter are content with sailing between snorkeling spots and sinking a few Painkillers at beach bars. Some want a dose of hard-sailing action blended in with their sunshine and warmth—the kind of action you can only get from sailboat racing.

And yes, racing and bareboat chartering can go together. Why not charter a boat and enter it in the BVI Sailing Festival and Spring Regatta, a week of sailing and partying that takes place at the end of March each year? As a veteran of a half-dozen Spring Regattas, I feel qualified to say that this is the ideal blend of sailing and apres-sailing, all set in the gleaming blue waters of the Sir Francis Drake Channel and around the islands surrounding it. It’s one of the greatest sailboat racing venues I’ve ever seen.

All you need to do is gather a willing crew—which should not be difficult— and charter a boat. Most bareboats entered for the regatta are chartered from The Moorings or Sunsail; both are regatta sponsors and are well accustomed to the demands of racing crews. They also offer the lure of one-design racing, since they have more identical boats in their fleets than most of the other companies. Ask your favored company if you’re allowed to race their boats.

This being a fun event, you can take it as casually or seriously as you and your crew want; there are always some teams who are there for the bragging rights that come with an overall win in one of the two bareboat classes and others who are perfectly content just to have the excuse to sail harder than they might be able to with their families. Indeed, it’s not unusual for teams to charter two boats, one each for the racers and non-racers, meeting up after the racing each day.

In keeping with that spirit, the rules are basic, limiting the extent to which you can “turbo” your charter boat. You may roll up the mainsail stack pack but must leave it attached to the boom, you can take off the bimini (in fact, you can gauge the “seriousness” of the crews by whether or not they leave theirs rigged) and you can tune the rig. You can re-lead sail control lines but you’re not allowed to use anything that’s not on the boat. There’s more, but you get the drift.

Our crew, Team Merlin from Marblehead, Massachusetts, scrubbed the bottom before breakfast each morning, showered copiously to leave as little water in the tanks as possible, and tensioned the rig on our Moorings Beneteau 48 until it hummed. All the tweaking paid off with a hard-fought victory against a host of Jeanneau 51’s in a week marked by some of the most enjoyable sailing we’ve had in the islands.

It began with a race around Tortola, which we shared with many of the racing-class entrants in the regatta, followed by a shorter race the next day to the Scrub Island resort. That took care of the Sailing Festival part of the event. After a layday, the three-day regatta itself kicked off, and we enjoyed some top-shelf on various courses among and around the islands before winding up with the awards party at Nanny Cay Marina.

It was a subdued bunch that filed onto the ferry to St Thomas next morning, but at least we remembered the trophy. 

Photos courtesy of Ingrid Avery

October 2019