I rarely give vacation advice, because vacation preferences are a highly personal matter. One man’s idyll is another’s hellish ennui, and everyone’s got a unique definition of fun. My globe-trotting colleague Jonathan Soroff classifies adventure travel as anything that involves thread counts below 600. Meanwhile, my friends Aaron and Carrie got scuba-certified just so they could dive the Great Blue Hole in Belize, which sounds like the kind of terrifying activity from which not everybody comes home. And in fact, the Great Blue Hole proved too much for one guy on their boat, making for a long ride back to the dock with a corpse for company. Call me soft, but I prefer to avoid mortal terrors of the briny deep.
So your vacation is not my vacation, but this is the time of year when thoughts turn to palm trees and beaches, and over the years I’ve heard one particular destination referenced in universally reverential tones and hung with the phrase “best vacation ever.” That would be a sailing trip with the Moorings out of their British Virgin Islands location. The concept is pretty simple: You sail around BVI on a private yacht with a crew to make your meals and mix your drinks and ensure that you make it from island to island without sinking or causing international incidents. (You can also try this without a crew, if your idea of leisure involves sewage pump-outs and crushing responsibility.) I know that a crewed charter sounds very Jay and Bey, but it’s not as expensive as you might think—in our case, about $1,600 per person for five nights, and that included food and booze. Calculate what you’d spend for Painkillers and mojitos over five nights, and the Moorings is like a Carnival cruise without the jorts and norovirus.
The tab was reasonably reasonable because we split it three ways between couples with our friends Steph and Ted and Dave and Michele. Each couple got a cabin on the 48-foot catamaran, with the fourth berth reserved for the captain and his wife, a South African couple probably in their late 50s. Our crew, who we’ll call Ahab and Rachel, were on their last tour of duty for the season and obviously sick of living on a boat with demanding vacationers, some of whom bring their own tiny bells to ring when they want something. Ahab, who had a beard and hoop earrings (as required by the International Code for Salty Fellows), lamented, “People think we’re stupid… Maybe we are.” I assured him I could get my own beers out of the cooler, especially since that was to be my main form of onboard exercise.
Ahab and Rachel’s initial wariness of us was exacerbated by a certain cultural hurdle, namely Ted. On a boat under way, there is a long list of things you must not do, and Ted delighted in informing Rachel that he’d done all of them. On the first day, as we sailed for a remote beach, I saw Ted emerge from below deck and say, “Hey Rachel, I put the toilet seat up and opened the porthole, just like you said!” This news was met with an icy stare as South African earnestness collided with the Bostonian penchant for busting balls. By the next day, she was just ignoring him, as is proper.
By the middle of the week, we were in a groove. We’d sail someplace more beautiful than the place before, then go snorkeling or hike around and explore, then go back to the boat and have cocktails. You’d spend the morning sitting up front on the bow, watching the waves roll past because there’s nothing else to do. Dave’s phone went dead on the first day, and he never recharged it. You’re just hanging out with your friends, sailing through these CGI cerulean waters and hopping off at white beaches framed by forested mountains. One day I stuffed a $20 bill in my pocket and swam to a beachfront bar. Have I adequately depicted how excellent this all was? I’m not sure that I can.
Of course, there are perils. Sometimes the crucible of close quarters causes interpersonal issues to emerge—we heard of one guy who locked himself in his cabin for a couple of days after a blowup with his shipmates. Other people, let’s say ones who don’t drink or swim or go outside, are odd candidates for a sailing voyage but somehow end up booking one anyway and then wondering why everyone says this is so great. And some people might party a little too hearty. “We had a guy come into a cabin and crawl into bed with someone,” Rachel said. “He was coming back from a bar and got onto the wrong boat. It happens all the time.”
On the last night, Ahab and Rachel seemed a little bit giddy—you could tell they were excited to get off the boat and go home for the first time in eight months. “Let’s tell her we decided to stay three more nights,” said Ted, before doing just that. For the first time all week, I wished he were serious.