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Old 03-22-2011
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There are only a handful of all-weather inlets along the Atlantic coast, so you need to be as careful about planning your trip as you are about selecting sails. You can still get caught with high winds on the inside route on the larger sounds in NC and the Chesapeake (if you go that way, via the C&D Canal and down Delaware Bay to the Cape May Canal), but you will have more options to seek safe harbor.

If you intend to go offshore for extended periods, you'll need to do more than select sails. You will need to consider inflatable PFDs with harness, jack lines, an EPIRB (which you can rent from BoatUS) and a life raft. There are also a lot of things you need to secure below and you also need to assure that you keep sea water out of your fuel and water tank vents.

Your best bet is to wait out questionable weather and not try to stick to a predetermined schedule. There's a lot to see and appreciate along the way, so it won't be lost time if you plan accordingly.

That said, I brought my own boat up from the west coast of Florida to Connecticut and practiced what I just preached. The worst weather we encountered was unexpected winds in the 38 kt range in the Chesapeake. We were able to duck into a harbor of refuge within a couple of hours.

Based on your original question, it sounds like you might want to recruit a crew member or two with appropriate experience if you go offshore.
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