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The Family Way

Before I actually took my family on a flotilla vacation, I couldn’t understand why anyone would take their family on a flotilla vacation. The mere thought of sailing along in a group of a dozen boats, being herded like sheep into marinas by some officious lead skipper, not to mention the forced jollity with total strangers, filled me with horror. After all, one of the reasons I go sailing is to

Before I actually took my family on a flotilla vacation, I couldn’t understand why anyone would take their family on a flotilla vacation. The mere thought of sailing along in a group of a dozen boats, being herded like sheep into marinas by some officious lead skipper, not to mention the forced jollity with total strangers, filled me with horror. After all, one of the reasons I go sailing is to get away from stuff like that. A bareboat and the freedom to go where I like, when I like—now that’s what I call a charter vacation.

But sometimes you have to sacrifice your own preferences for the greater good. The children—then aged 4 and 6—viewed sailing as a means of transport from one beach to the next, and were vocal in their dislike of the passages between anchorages. They missed their playmates and keeping them entertained while sailing the boat wasn’t much fun for the adults either. As any parent knows, if the children aren’t having fun, neither are the adults. There had to be a better way, and perhaps a flotilla was it.

About three days into our first flotilla vacation in Greece’s Ionian Sea, I was wondering what had taken us so long. The kids were playing happily with some new friends and we were exchanging war stories with their parents, who had gone flotilla sailing for much the same reasons as us. It was the beginning of a family tradition that continued for the next five years, through more flotillas in the Greek islands and Croatia.

That first charter laid to rest my preconceptions about flotilla sailing.

#1 — Flotillas are for the nautically challenged. In fact, skill levels varied as much as you’d find in any group of a dozen boats, anywhere. Boathandling caused some initial grief for small-boat sailors who had never docked a big sailboat under power, but with the guidance of the lead crew they were soon backing up to quays like old hands.

#2 — You have to sail in a pack. Not so. Flotilla skippers are completely okay with you wanting to spend the night in a different anchorage or head off on your own for a few days.

#3 — You have to spend shore time with people you don’t know. This is up to you. Apart from briefings, there are no forced get-togethers. You can join in the parties and meet other people, or keep to yourself.

#4 — You’re told when you have be in a harbor. Aside from the usual charter rule of not sailing after sunset, I’ve never found this to be the case.

There’s no doubt that many first-time charterers find the presence of an ever-cheerful lead crew—skipper, engineer and hostess—to be reassuring. Having someone on hand to help you into or out of a gnarly spot, take your lines, reset your anchor, unwind an errant dinghy painter from your propeller or unblock your toilet is a luxury that I am not ashamed to enjoy.

Knowing that local experience has gone into organizing the itinerary is also a good thing if you want to concentrate on sailing rather than route planning. No lead crew is going to take you anywhere not worth going to.

But my overriding memories of those long-ago flotilla vacations are of groups of laughing children splashing in the shallows; passing cocktails around the cockpits of three or four boats during impromptu raft-ups; and meeting good sailors who became good friends. They were great times, and proof indeed that preconceptions are often dead wrong.


Ready for a family flotilla of your own? From June 10-17, join SAIL and Sunsail on a Family Fun Flotilla in the BVIs. We’ll island hop with a Sunsail lead boat hosted by SAIL’s charter editor Meredith Laitos. In addition to hands-on sailing for kids and families, you can expect a week of family fun, including dinghy races at the Bitter End Yacht Club, paddleboarding in the Baths and treasure hunts. If you crave spectacular island scenery and sailing camaraderie for kids from 1 to 92, this is your ideal summer vacation.

To learn more about Flotilla Adventures from SAIL and Sunsail, call 800-736-9539, or click here.

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