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- Owning a non trailer-able sailboat gets old. I sail on arguably the prettiest part of the Chesapeake, where the Bay meets the Patuxent River, up from the Potomac River. Even so, sailing in the same waters over and over becomes tedious.
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I guess it depends on where you are, but I dont get sick of it 1 bit. There are hundreds of miles of shoreline to explore, rivers, towns, anchorages... Not to mention going offshore, down the ditch... At the same time, I like to just tie off the tiller and cruise down the Magothy or under the bridge and call it a day.