Some like it hot

According to received wisdom, there’s no point in going to the Caribbean in the summer. “Too hot,” the naysayers grumble. “And if it’s not too hot, it’s too wet. You’d have to be pretty dumb to go down there in hurricane season.” All of which is true, and also not true.Yes, it can be hot, yes, it rains more than in winter and yes, there is the chance a marauding
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According to received wisdom, there’s no point in going to the Caribbean in the summer. “Too hot,” the naysayers grumble. “And if it’s not too hot, it’s too wet. You’d have to be pretty dumb to go down there in hurricane season.” All of which is true, and also not true.

Yes, it can be hot, yes, it rains more than in winter and yes, there is the chance a marauding hurricane might meander over your little patch of the islands. But on the other hand, rumors of unbearable weather are much exaggerated. I haven’t found the summer temperatures to be significantly higher than in winter. You’ll get some rain, but in my experience, prolonged downpours are the exception rather than the rule; the islands still average 9 hours of sunshine a day in summer.

Nor have I found humidity to be a problem, at least not around the island coastlines. I’ve suffered through many muggier August days in Massachusetts than I’ve experienced during summer vacations in the BVI or the Grenadines.

You shouldn’t obsess about hurricanes, either. The National Hurricane Center says most big storms miss the Windward and Leeward islands, and long-term weather predictions are pretty good. Charter company base managers are extremely knowledgeable about conditions in their own stamping grounds and it’s not in their interests to have boats full of clients stooging around exposed anchorages if a hurricane is imminent.

It’s far better to dwell on the positives of the Caribbean summer—cheap flights, empty beaches, and uncluttered anchorages. You can usually strike a good deal for a boat, especially for last-minute bookings.

I still have fond memories of a week in the Grenadines some years ago, when a group of us booked a Beneteau 473 out of St. Vincent in the first week of August. We reeled off nearly 50 miles the first day, enjoying a beam reach to Carriacou, just north of Grenada, in 20 knots of trade wind. Then we spent the next six days pottering back via the Tobago Cays, Union Island, Mayreau, Mustique and Bequia.

There were plenty of other charter boats out, mostly crewed by stalwart Brits and Frenchmen who know a good deal when they see one, but we were easily able to get away from other boats when we wanted to.

The weather? A few showers each night, the odd, easily-spotted, short-lived squall during the day, but mostly blue skies and a warm 15 to 18-knot easterly breeze. It was a great week of sailing, and I’d do it all over again.

We had booked last-minute flights, after first scanning the Atlantic weather maps for lurking tropical depressions that might morph into something nasty. If LateSail had been around then, we might well have used that, too. This British company has just opened a U.S. office. It specializes in hooking people up with inexpensive, last-minute bareboat charter deals. U.S. operations director James Gilbert says LateSail works with around 100 charter companies worldwide. Anything that gets you a better deal can’t be bad.

Flotilla news

I took the family on a few flotilla vacations when the kids were smaller, and a great time was had by all. There were always a few other boats with children aboard, and we all made some good friends.

Sunsail and Horizon Yacht Charters have come up with new angles on flotillas. Olympic sailor Zach Railey will be the guest star on the “Racing with Railey” flotilla vacation in the BVI from November 6-13. There’ll be low-key beer-can racing, lots of family activities, and a chance to get Zach to help improve your sailing skills.

Horizon will break new ground with a November flotilla sailing from the BVI to the Spanish Virgins, Culebra and Vieques. As far as I know, this has never been done before, and it seems like a good chance to explore these uncrowded islands.

Horizon also has a competition that will net the winner not only a week’s charter, but also a day with America’s Cup helmsman Peter Holmberg as your skipper. Entries close on August 31, so be quick.


Conch Charters, 800-521-8939.

CYOA Yacht Charters, 800-944-CYOA

Footloose Charters, 888-852-4666

Horizon Yacht Charters, 877-494-8787

Sunsail, 800-797-5309

TMM Yacht Charters, 800-633-0155


Star Clippers, 800-442-0551



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