By Eileen Ogintz
Tribune Media Services

For once, we’re masters of our own destiny — in paradise, no less.


Now if we can just survive the week of togetherness!

Our entire crew on the Moorings cataraman Mary Morgan III

My far-flung gang has come to the British Virgin Islands — the undisputed Sailing Capital of the World — for a week aboard a chartered Moorings sailboat. It is the first time my husband and I and our three kids (plus my daughter Reggie’s boyfriend) have been in the same place at the same time in more than a year. My youngest daughter has just returned from a semester abroad; Reggie and Dan live and work in San Francisco; my son works and attends graduate school in New York. My husband and I live in Connecticut.

I was desperate to figure out a way to get us all together away from home in a place we’d all enjoy. A sailing trip was their top pick — we’d happily done it before. The British Virgin Islands have long been popular with sailors because of the constant winds and the fact that you are rarely out of sight of land. It’s no wonder then that more than 700 sailboats and yachts, the largest fleet in the Caribbean, are moored in Tortola. The Moorings has been in business for more than 40 years here and this trip we’re aboard a 46-foot Catamaran with four cabins — the largest boat we’ve ever sailed ourselves.

Everywhere we look here there is turquoise blue sea, bobbing sailboats, cruise ships and mega yachts, not to mention the small islands off in the distance. (This is an archipelago of some 60 islands, after all.)

The best part: There is no one telling us what time we have to eat dinner or even where we are going next. Welcome to the alternative to mega cruise ships and fancy resorts.

My three kids, Matt, Reggie and Melanie, all experienced sailors, nixed the idea of a captain, much less a cook, though that certainly is an option on charters. (Captains cost $185 a day.) Being the master of your own vacation destiny can be cheaper than you might think, though, certainly cheaper than a big resort where you’re paying $5 for a soft drink, double that when the kids are old enough for alcoholic concoctions. Sailboats with two cabins start at around $330 a day. Look for the latest deals on

This is our third sailing trip in the Virgin Islands, though our first in six years. I joke that I don’t think we’ll be searching out women to braid the girls’ hair this trip, or that Melanie will fall asleep at dinner. “You just have to chill, mom,” says Mel, who, like her older sister, has taught sailing. “You don’t have to take care of everything anymore!”

Certainly, I don’t expect everything to go as planned. It never does when kids, no matter how old they are, are part of the equation. But it’s still hard to let go of those expectations when the kids bicker (sibling issues don’t disappear in paradise), it rains (and I forgot my rain jacket), food freezes in the small fridge (it happens no matter what we do) and I discover I’ve forgotten the meat for our planned fajitas dinner.

“We’ll eat veggie fajitas,” my daughter Reggie says with a shrug. “This is an adventure, not a resort where everything is done for you!”

She’s right. And that means the most memorable aspects of the trip will likely be what I didn’t plan or anticipate — from the kids beating me at Scrabble (I used to be the family champion) to my husband diving 40 feet — literally — to retrieve the top to our dinghy’s motor, which fell into the water when he tried to repair it. (Thanks Sail Caribbean for lending us the needed gear after our dive), to Melanie’s regaling us with her expertise on reefs after a semester studying environmental issues in Thailand.

We wake up with the sun in a place where pirates once ruled. The British Virgin Islands is not nearly as developed as the U.S. Virgin Islands so the ambiance is far more relaxed, especially offshore. We jump from the boat to snorkel and swim. We eat gargantuan lobsters on the island of Anegada, home to just 300 people and famous for its lobsters. The kids try windsurfing and paddle-boarding at The Bitter End Yacht Club on Virgin Gorda, which boasts an unparalleled array of watercraft for sailors and guests.

The biggest issue of the day — besides where to go — is whether we have enough ice. A trip like this requires that you be willing to let go of some of your creature comforts. We may have a blender and microwave on board, but we’re the only dishwashers and we’ve got to pump the water after a shower that isn’t always hot.

“Who cares!” my kids say. When the watermelon freezes, they use it in drinks.

Along the way, Reg and her boyfriend, Dan Foldes, will become certified divers, thanks to PADI’s online course and Sail Caribbean Divers, which also has run summer teen programs here for more than three decades. We’ll dive together as a family (more about that in another upcoming column), snorkel, kayak and most importantly, catch up on our lives.

It takes a lot of pulling together on a trip like this — from deciding our course to what to make for breakfast, putting up and taking down the sails, deciding where to moor the boat and getting the dinghy going when it stalls. We can’t just get away from one another either — short of jumping off the boat.

We disagree — sometimes loudly — over sailing technique, what to cook for dinner, whether we need more beer, as well as some more important issues of the day. A floating mat we’ve rented from Last Stop Sports blows overboard.

At The Bight, an anchorage and long-ago hideout for pirates, located on Norman Island, just a quick sail from Tortola where we started, there is no one else around but other sailboats. When I offered the kids the chance to go eat at the waterfront restaurant, they said they preferred a just-us dinner onboard our boat.

I smiled. That was the point, after all.

For more on this sailing trip through the BVI, please read Eileen’s Travel Diaries