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Old 02-16-2012
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The Harbor Inn Marina and the St. Michaels Marina are pretty comparable in facilities. Both have small pools, on site restaurants, clean bathrooms, etc. They're both walkable to the town and museum, though the St. Michaels marina has a slight edge in proximity. The Harbor Inn could probably be considered more family friendly due to not having two outdoor bars right near the docks. Cheap dockage is available at the Maritime Museum with a membership, but there's no pool.

If you're not in that part of the Bay often, you should definitely visit the Wye and drop the hook in Dividing or Granary Creeks. From there you can dinghy to Wye Island, most of which is a state park. Shaw Bay in the Wye and Leeds and Hunting Creeks in the Miles are also great, relatively unspoiled anchorages.
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