The Moorings, which had its most successful year ever in 2023, seems to have figured out the secret sauce that makes chartering an easy and approachable vacation for even novice sailors and more wary travelers. It’s so easy it feels a little like cheating.

Much of the chart briefing and safety information was offered to the crew online ahead of the trip, which meant our checkout the morning after we slept onboard at the base was a pretty seamless affair, and we were shooting the gap at the base by 11 a.m.

They say you should never sail upwind on vacation, but that’s exactly how we started our trip, tacking to Leverick Bay in a 20-knot northeast trade wind and dodging intermittent showers along the way. On a boat like the 5000 with its numerous lounging areas and cockpits, its hardly a hardship to sail through a shower.

Our zigzag course took us close to islands we’d never paid much attention to including Ginger Island and Salt Island, where a dive boat was tucked in to a small cove. We dropped the main as we passed the Dogs, avoiding a small squall, then powered past the minuscule Moskito Island to enter the channel to Virgin Gorda, avoiding the tempting but verboten shortcut between Anguilla Point and Moskito, unlike at least a few previous charterers of the boat had done, as evidenced by the many tracks stored on the chartplotter.

With a mooring secured—the mooring ball system, both those owned by businesses onshore and those maintained by the online reservable Boaty Ball service, is one of many aspects of the BVIs that’s gotten a major upgrade to keep up with the increased demand—we took a stroll around Leverick Bay Resort, with no agenda other than to take a compulsory trip ashore before enjoying a sublime cocktail hour and dinner aboard.

When we woke the next morning we remarked at how the wind hadn’t let up all night, and by the time we slipped the mooring at mid-morning it was piping up even more. It wasn’t a question of if we should reef, it was a question of whether it should be one or two reefs. 

Our destination was Anegada, the so-called drowned island that sits at just 28 feet above sea level at its highest point, and we weren’t alone: a steady stream of boats were also taking advantage of the boisterous but entirely enjoyable conditions to sail from Virgin Gorda. It was our good fortune that one of them was a sistership, and we sailed up on their hip not in an effort to take out the pent-up desires of a bunch of a racing sailors hungry for competition, but to get in a photoshoot. With the unrelenting breeze, we were dreading having to negotiate a typical photographer-in-the-dinghy style shoot.