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Seeking Exciting and Unpredictable Challenges Offshore

On my latest ocean passage, aboard the 46-foot sloop Callisto, we set sail from Hampton, Virginia, with the fleet of close to 80 Caribbean 1500 boats bound for Tortola. The air was crisp and cold, the wind from the north and on the stern, and once clear of Thimble Shoals, we cracked the sheets and eased our way out of the Chesapeake. In the eight days that followed, the crew of Callisto (who'd never been offshore before), learned about their boat and about themselves, and came to understand that ocean sailing remains a highly personal endeavor, a daunting challenge and, with the right attitude, one that can be incredibly rewarding.

The weather, as usual, proved unpredictable – a late-season Hurricane was flirting with the Caribbean, and a series of low-pressure systems were tracking northeast across the American continent. We ended up stuck in Hampton for longer than we were offshore.

As the skipper/instructor aboard Callisto, I encouraged the crew to stay focused during the delay. The activities grew repetitive, but we kept it fresh by completing odd jobs on the boat (like whipping line-ends in the cockpit), pre-cooking lots of food and engaging in a three-hour lesson on celestial navigation. The day before the actual departure we again went over the rig, hull and engine, repeating the process of a week before.

Once offshore, Callisto took flight, broad-reaching along the coast as we headed southeast towards Cape Hatteras. The first 12-hours sailing in flat water under the lee of the land proved a wonderful warm-up; a chance to get our sea legs before taking our departure from the coast, a chance to get a good hot meal in our (sometimes tender) bellies, and a chance to work out the kinks in our watch rotation.

By midnight we were in the Gulf Stream, off soundings, still flying along at over eight knots through an increasingly boisterous sea that would remain with us for the next eight days. The low-pressure system that had ultimately delayed us remained stationary to the north of Bermuda. It was an odd weather pattern and provided the fleet with challenging downwind sailing in 20-25 knots for the entire week.

We experimented with a variety of downwind sail combinations, trying to get the most out of the boat, while the owners (David and Gretchen Cantor, with their son Aaron) gained valuable experience handling sails offshore. The wind blew hard enough so that mistakes would not go unnoticed – we narrowly avoided damage when we accidentally jibed while shaking out a reef, and did in fact tear our mainsail during another mishap. Thankfully these instances proved to be excellent learning experiences and nothing more serious. Modern cruising boats are ever increasing in size; the instant something goes haywire they become a real challenge to handle, a fact that became more apparent to Callisto's keen owners as we made our way south.

With the boat surfing over 15 knots at times, going forward was a challenging prospect, but both David and Gretchen managed the feat, setting and dousing the pole, reefing and unreefing the mainsail and setting up the preventer. Callisto had nylon webbing jacklines running the length of the boat, and the crew remained attached to the boat at all times. Navigating the bevy of lines on deck at night, however, was no easy task.

Two hundred and fifty miles out, the cooperative breeze finally died as we inched further south away from the center of low pressure (which remained near Bermuda). We ambled along under full sail for the first time, while the big ocean swell gently urged us along. We donned shorts and T-shirts, even at night; in stark contrast to the sweaters and full wet weather gear we had worn at the beginning of the voyage.

By daylight, land was in sight. I did not anticipate the aroma. The simple smell of land; the flowery and smoky fragrance that wafted over the boat as we rounded West End, Tortola, triggered wonderful emotions from my previous visits here, emotions that I wasn't prepared for, that caught me off guard and made me realize how much I'd missed this place, the tropics. For all the crowded harbors and charter boats, there is something here beyond comprehension that makes it feel absolutely wonderful to return. As we made our way in, under sail, I enjoyed a peaceful moment of satisfaction that can only come with the completion of a major challenge, over a week offshore – a long-term goal in the Cantor's case – and I hoped that moment was as meaningful to them and the rest of Callisto's crew as it was to me.

Andy Schell is a professional captain and freelance writer. After the fall sailing season, he and his fiancé Mia Karlsson will return to Stockholm for the winter. Next summer they plan to sail their yawl Arcturus across the Atlantic to Sweden. Contact Andy online at fathersonsailing.com.

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