OK, OK, if we leave at dawn we’ll be able to arrive in Anegada before sunset, assuming we’re stopping at Guana Island to snorkel. Suze might want to go surfing at Loblolly, and we should have a lobster at the Anegada Reef. But then we need to plan when we’re getting to the Baths, so we can’t spend too long there, and what about the Bitter End?”
Stop! Freeze everything. What are we trying to do? This is a bareboat charter, not a cruise ship activities desk. Why don’t we just see where the wind takes us and enjoy the moment, I suggest. And we did precisely that, and our loosely planned bareboat charter in the British Virgin Islands this past February is still firmly planted in my memory as one of the best.
I admit that some people become extremely frustrated with my fondness for a simple itinerary. Sure, I think it’s important to have a rough idea of where you’re going and to ensure your guests see special places, but the pace of such a cruise needs to be dialed back in order to reach relaxation mode. Fortunately, on this trip I was joined by my old friends Jack Bulger, his wife Suzy Kraft, their daughter Sienna and Kathy Gallaher — and they each embraced all of the special benefits of the nonplan plan.
After 15 years of chartering in the Virgin Islands I’ve realized that the key to a memorable trip is to spend more time doing less. There is no way you can stop at all the special places the Virgin Islands offer and actually have the time to enjoy the surroundings. There are, however, a few spots I include as must-sees, and then each year I try to sprinkle in around these another place or two. My must-sees include White Bay on Jost Van Dyke; Gorda Sound including Saba Rock; and Bitter End Yacht Club; a snorkel layover at the Indians; and Cooper Island. That’s it!
This charter with Voyage, located in Soper’s Hole in Tortola’s West End, was my first sailing charter — and I was hooked. Jack and I have had our share of sailing “adventures,” including one plagued delivery with Suzy to Antigua that dealt us gale-force winds, a leaky boat, a slightly crazy crew member and morning sickness. (It turned out Suzy was pregnant with Sienna!)

Freedom Chaser, the Voyager 500 catamaran we chartered this time, provided the exact opposite experience. She was in superb condition, a spritely performer and extremely comfortable. Ever since our Antigua death march, I felt it was my solemn duty to make Suzy realize that sailing can actually be enjoyable. Engines do work, refrigeration can keep food cool, and not all boats come equipped with a bipolar crew member who doesn’t know how to lift the toilet seat and who hits himself, screaming, “I’m bad, I’m bad!”



