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Conventional wisdom has it there can be only one captain on a boat, and that skippering by consensus never works. When it comes down to the wire, one voice must be heard above all others, or chaos will ensue. Well, that’s obviously a male viewpoint. My friend Pip and I share a passion for sailing and adventure, and we’ve done some offshore racing and family cruising, but neither of us had ever
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Conventional wisdom has it there can be only one captain on a boat, and that skippering by consensus never works. When it comes down to the wire, one voice must be heard above all others, or chaos will ensue. Well, that’s obviously a male viewpoint. My friend Pip and I share a passion for sailing and adventure, and we’ve done some offshore racing and family cruising, but neither of us had ever taken charge of a sailboat. Our confidence had been bolstered by a rigorous sailing course that qualified us to skipper a charter boat. It also revealed that we have different but complementary skill sets, so we decided a collaborative skippering experience might work best for us. With no male egos to get in the way, the omens were good.

We approached our charter in the British Virgin Islands with a heady mix of excitement and nervous anticipation, reasoning that our combined sailing knowledge would see us through the week. We had no reason to doubt our individual abilities, and felt comforted by the fact that we had each other to rely on, confer with and learn from.

Two skippers need a strong crew. We assembled a dynamic bunch of women from New England and old England to accompany us. Bird provided crucial sailing assistance, as well as psychotherapeutic advice. Aviva recorded our daily exploits with beautiful watercolors, while Jen created exquisite meals with fresh local ingredients. The week’s entertainment culminated with a truly memorable water ballet performance directed by Pam and featuring The Water Sisters.

The Footloose charter base on Tortola is wedged behind pontoons bulging with Moorings and Sunsail boats; we wondered if we’d have to grease the sides of Sail Mate, our 43ft catamaran, in order to get out. A terrified Pip took the wheel for departure and set off rather faster than anticipated, blaming the throttle controls. After a rather hairy snorkel stop at the Indians that involved 18-20 knots of wind, a large swell and pushy bareboat skippers ready to play chicken for the nearest mooring, we made the Bight on Norman Island with plenty of daylight to spare. It was a pleasure to see everyone so excited, especially those who had never been in the Caribbean before. We swam, enjoyed the sunset, and then shared a superb dinner followed by—ahem—pole dancing.

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Pip had been to the BVIs enough times to know the importance of arriving early at the Baths. But when we arrived still bleary-eyed the next morning, we were met by red danger flags on shore snapping in the 20-knot northeasterly breeze. No problem, we’d just pick up a mooring so Aviva could do some painting. You can guess what happened next. Somehow we ended up wrapping the dinghy painter around our prop. Yes, I admit it, panic ensued: cursing, engines refusing to start, big swell, rocks—yikes! Then we realized we were drifting away from rocks and other boats, and that we were in no real danger.

We bent on a new painter for the dinghy so we could cut free the wrapped line. Thankfully, Bird is always up for a physical challenge. Topless, fearless, knife clenched between her teeth, she was soon over the side doing battle like a Bond girl. Not to be left out, Aviva and Pip joined the struggle and managed to pull the last piece of yellow line from the prop. The only casualty was a lost boathook—amazing! We dusted ourselves down, breathed a huge sigh of relief, and then had a cracking sail up to the Bitter End.

Trouble always comes in threes, and as we prepared to depart the Bitter End, the port engine refused to start. Fortunately Lionel, a roving mechanic from Footloose, came to our rescue, fixing the engine and replacing the boathook and painter. Moored at Leverick Bay that night, we went ashore to see a really corny pirate show. Inspired, we returned to the boat and had our own limbo dancing competition.

The next morning we decided to confront our demons and return to the site of the by-now legendary prop wrap. This time there was much less wind and swell at the Baths, and we arrived early enough to have our pick of the moorings. We went ashore in the dinghy and had a lovely few hours exploring the caves and swimming in the crystal clear water. By lunchtime all the tourist buses were gone and we had the place to ourselves. The disaster du jour was losing the kill-switch clip from the dinghy, but Aviva’s hairclip made a wonderful MacGyver-style substitute.

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