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Picking a Charter Destination

The best charter destination is the one that fits your needs

The best charter destination is the one that fits your needs

Picking a destination should reflect the interests of your group, says People often ask about my favorite charter destination, and invariably, I sidestep the question with one of my own: “Well, what do you want to do on your vacation?” Most often I hear an incredulous, “Why, sailing, of course!”

The truth is that vacations run to a schedule. They need to cover a lot of ground and meet expectations of diverse family members and friends. By day three of a charter, you sail when you can and motor when you have to in order to make it to the next snorkel spot, land tour or drinking establishment.

Most of us find sailing is a nice plus on a charter vacation, but too often there’s no wind, too much wind or the right amount of wind but from the wrong direction. There’s a reason those boats have engines, you know.

For example, in the British Virgin Islands, you can’t ever seem to get from Nanny Cay to the Bitter End Yacht Club without an afternoon of tacking, dismayed by your VMG. In Greece, you may be slogging to weather during a Meltemi wind to make it to the next safe harbor during daylight because Med mooring in the dark sucks.

So besides sailing, you’ll need to choose your charter destination based on what you want to see and do as a tourist. Are you looking for a variety of rum cocktails and ample shopping? Then the BVI will do nicely. In Mexico, you can’t possibly find more T-shirt shops and beach bars, and the sailing is easy with line-of-sight navigation. If you want to contemplate life with a cooler of beer and a book surrounded by idyllic white beaches, try the Tobago Cays in the Grenadines. You can spend a week here, snorkeling with sea turtles, kite-boarding and limiting your socializing to a beach BBQ.

For a step back in time when cruisers were still exotic creatures to local island populations, Tonga is your best bet. The cruising grounds of the Vava’u Island group are tiny and the people so genuine that you’ll find yourself lingering just to chat with them awhile and wondering how time has stood still in the middle of the South Pacific.

If you’re a photographer, the colors of the reefs of Bora Bora and Huahine will make you want to buy a drone. Almost the definition of a tropical paradise, Tahiti lures young honeymooners and crusty old sailors alike. Point your lens in any direction, and you’ll look like a pro.

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Of course, it’s not just your vacation. You’ll likely have a spouse, friends and maybe kids along so you need to think about their enjoyment too. If a tooth extraction is easier than getting your mate on a boat, you may want to consider bribes like offering up stunning history and magical culture. In that case, head to Europe. Whether the lure is wine tasting in Italy and France, medieval forts and castles in Croatia, or the mesmerizing power of ancient Greece, there’s much here to use as bait. And if you feel you must prove your seaworthiness somehow, remember that you’ll get plenty of opportunities here to try your hand at Med-mooring, which can be more challenging than sailing.

When chartering, especially at international destinations where you go through the hassle of flying in, you want to consider the place on its own merits. Study the location, plan the excursions and anchorages, and check the weather. Then just do your best to sail regardless of the wind.

If you’re still set on sailing from dawn to dusk, consider a local charter if you live by the water or sign up for some training with a sailing school. And before you tell me how you don’t need sailing school, remember that none of us can ever know too much about trimming sails and estimating set and drift—and if that doesn’t make for the most fun family vacation, consider going it alone. 

Photos Courtesy of Zuzana Prochazka

September 2019

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