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Home » Travel Tips

Cruising Maryland’s Eastern Shore

Submitted by on 12/07/2016 – 5:16 pmNo Comment
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Hoopers Island

Photo from Flickr by Urban Hippie Science

The eastern Chesapeake Bay offers some of the best sailing in the United States, and a yacht charter from Annapolis is the ideal way to see it. The bay can make for some challenging navigating, but it would be a shame to not visit the nooks and crannies on the Eastern Shore. You’ll be rewarded with a wealth of options for nature walks, kayaking, and great food pulled fresh from the water.


Hoopers Island

A nice route out of Annapolis Bay would be to sail south as far as Solomons and reach over across the bay to Hoopers Island. During the day, visit Hoopers Island Oyster Aquaculture Co. to learn all about farming the bivalves native to the bay. HIOAC is also active in the restoration of the Chesapeake Bay, working to preserve the fishing way of life while also making it sustainable and non-destructive for the environment. If you’re into oysters, this is a fun way to learn about them. In summer, the company takes small groups out on its boat to see oyster cultivation first hand. Reserve tickets online.

There are public harbors in the area, but wherever you choose to stay, be sure to eat at Old Salty’s. It’s not fancy – perfect for the shorts and T-shirts you packed for the week – but it’s loved by locals and visitors for classic dishes of the area, such as crab cakes and seasoned steamed shrimp by the pound. Old Salty’s is open Wednesday to Sunday from 11 a.m. to 8 p.m.

Cambridge, Dorchester County

Sail north, passing Taylors Island and head into the Choptank River to Cambridge. There are many worthwhile stops in this area, but Cambridge offers a lot of sites within walking distance of each other and a lovely marina. Of particular note is the Harriet Tubman Museum and Educational Center. Part of a network of sites chosen for their historical significance as part of her life and the Underground Railroad (called the Harriet Tubman Underground Railroad Byway), a visit to the museum is particularly timely with the renewed interest in her legacy.  It keeps limited hours from Tuesday to Saturday, and a good place to orient yourself in this county is the Dorchester visitor center.

You could provision your boat like a VIP all up and down the Eastern Shore, but why miss out on the land-based eating experiences? Your biggest dilemma in Cambridge will be choosing where to have that 5 o’clock cocktail followed by locally caught seafood. For picnics and on-board meals, don’t miss buying local produce at the farmer’s markets – or at the farms themselves.

Set out for the Eastern Shore with an Annapolis yacht charter and you might well find yourself longing to return every summer.

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Blanche has written 758 articles. +Aaron Bradford is the leader, mentor and chief geek of HappyTimeblog. He put together the crack team of writers known by codename “The Firm“. He's a permanent traveller and a lifestyle hacker. Wanna know more? Check out my Bucket List or my About page... I'm here to show you how to live a Life Less Ordinary

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