I will be stopping in the Chesapeake on my way to Florida in the fall—any hints as to how to get the best exposure to it in the week or two I’ll be sailing there? Thanks, Will
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There are so many sides of the Chesapeake and I don't just mean Eastern v western shore.
Some people are afraid of Baltimore. We love it. Great restaurants, taverns, museums, I've been told the buses are free on weekends. Camden Yards if you're a baseball fan. We sailed to Baltimore for one of the tall ships weekends and will never, ever sail there during that type of event again. It was harrowing.
If you want a mix of touristy and non-touristy, I would suggest anchoring out in some of the tributaries and coves as much as possible. A sail up the Chester River is worth it, especially if you're a fan of John Barth's Friday books.
Take a day to visit the navel academy in Annapolis. That could very well take an entire day and you still won't get through everything. The Annapolis water taxi is reliable and easy to use.
Back across to the Eastern shore, the Wye River area is beautiful. We anchored in Tilghman Cove, which only fits about two boats comfortably. A man came out onto his lawn and played his guitar for us. Shaw Bay on a night with a full moon? Magical.
West River has good anchorages.
Beyond that, I'm afraid I've only sailed through to get out to the ocean. We haven't really stopped to explore. I'm hoping to change that this year.
A warning: we discovered that some channel lights in the Hampton, VA area are solar. We discovered this motoring up the channel at 3 am. By that time the lights are off completely.
Others, I'm sure, can fill in some gaps. Let us know when you're in the area.