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Old 02-21-2008
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You'll probably want to go outside from Buzzards Bay down to Cape May, and then head up the Delaware and over to the Chesapeake Bay. Be aware that going outside generally will require some overnight sailing, and that the New Jersey shoreline can be a very nasty and dangerous one in bad weather, since many of the harbors there are not safe to enter in bad weather.

Once on the Chesapeake, you'll head down the bay until you get to the ICW and take that down to Florida. However, by leaving in October, you'll be dealing with the tail end of the hurricane season, and will need to keep an eye on the weather and have a list of possible hurricane hides for the area you're in at any given moment.

As many of the people, like PBZeer and Camaraderie can tell you, doing the ICW is generally a matter of motoring rather than sailing, and awfully boring and slow if you're by yourself. Doing it without crew may be very painful.

I hope you're not planning on sailing to a schedule of any sort, since that is unwise at best, deadly at worst.

Cam and others will probably give you some excellent advice about making the hop across to the islands and where to go...
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Telstar 28
New England

You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.

—Cpt. Mal Reynolds, Serenity (edited)

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