As soon as anyone learns that I’m a charter captain, invariably the question comes: “Where’s the best place to charter?”
If you’ve ever read TripAdvisor or Expedia reviews, you’ll note that “best” means a lot of things to a lot of people. I know that whatever answer I give, it rarely satisfies. I’ve learned to take a breath and try to size up the asking party about what they would consider “the best” because they’re not really asking me about my favorite, they’re asking me about theirs.
I try to explain that those interested in history and culture will enjoy Greece, Italy, and Croatia in the Med, while those looking for more remote and exotic locales should investigate Tahiti or Tonga. And if bars, beaches, and shopping feature prominently on the agenda, the Caribbean, specifically the BVI, makes a good target. The toughest thing for people to grasp is that whatever they choose, the best is what they make of it.
Expectations vary wildly by person and by day. One year we had a group of eight boats in French Polynesia, arguably a bucket list destination. Even today, Tahiti is relatively remote, mostly undeveloped, and stunningly beautiful. The beaches are white, the water is warm, and if you know where to go, you can snorkel with manta rays as they glide below hoovering up breakfast. One guest, however, found nothing to her liking over the course of the week, whether it was the people, the prices, or the French-Tahitian cuisine. “Well, there’s always the amazing swimming,” I offered.
“It’s toilet water,” she threw back at me and stomped off in search of a Pacific Ocean of white wine.
In Croatia, one guest fought the imaginary windmills of tourism, calling parts of Split and Dubrovnik “ridiculous Disneyland.” It’s true that you can quickly overdose on stores hawking Game of Thrones memorabilia, but the depth and richness of history oozes from every medieval stone. Maybe look past the calamity of tchotchkes and enjoy an Aperol at a cliffside cafe, contemplating the legions that came before.
In the Exumas, where it seems all hues of colorful blue water are born, we were enjoying a lovely beam reach when one guest who was new to sailing muttered, “It’s just the same water no matter where you go. It never changes and is never new.” Well yes, it is water.
Over the years, I’ve taken a few groups to Delos in the Greek Cyclades Islands. The whole island is an archeological dig with thousands of years of history and remarkably preserved structures. Mostly, my groups lasted 10 minutes before scattering, with some of the younger ones donning headphones and dancing through the ruins to Katy Perry. You can lead the proverbial horses to water, but you can’t make them enthusiastic about drinking.
The worst part is that some people love sailing and exploring while others barely remain conscious out of sheer boredom. And they’re usually all on the same boat, so what do you? The dilemma of being everything to everyone befalls all charter skippers, especially those who bring along a variety of friends and family, young kids, those prone to seasickness, and teenagers who are hard to impress in the best of times. When planning your charter vacation, you too will be faced with threading the needle of diverse interests.
The “best” approach is to plan ahead, share your details, create excitement, and get buy-in from as many of your party as possible. Then stay a half-day ahead of the group by religiously reading the cruising guide and furiously mixing culture, shopping, and maybe a lunch at a luxury spa. One of those is bound to be “the best” for at least one person aboard.
The above question replays at most of my boat shows, speaking engagements, and cocktail parties. Despite a genuine effort on my part to be helpful and informative, some people decide that there surely must be a “best” answer and that I’m just hedging, so they glaze over and then follow the proffered party tray of champagne glasses to easier conversational pastures. I don’t take it personally because I know that on any given charter with six guests, four will love it, one will be nonplussed, and one will find a way to hate everything.
“Best” is a confounding concept, at best.
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November/December 2024
