Charming cobblestone streets, a prime location on the Chesapeake Bay and centuries of history make Annapolis a great destination for a relaxing weekend trip.  www.casualtravelist.com

Charming cobblestone streets, a prime location on the Chesapeake Bay and centuries of history make Annapolis a great destination for a relaxing weekend trip. www.casualtravelist.com

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In Annapolis, Maryland, crab is king. Stuffed in omelets or held together in crab cakes, crab - in all its forms - is the heart of Annapolis food.

In Annapolis, Maryland, crab is king. Stuffed in omelets or held together in crab cakes, crab - in all its forms - is the heart of Annapolis food.

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Things to Do in Annapolis During a Day Trip

Things to Do in Annapolis During a Day Trip

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Annapolis, Maryland: I love to walk this quaint street and wander into the bookstores,  art galleries with the nautical art, and great little restaurants. George Washington ate or slept at some of the places here!

Annapolis, Maryland: I love to walk this quaint street and wander into the bookstores, art galleries with the nautical art, and great little restaurants. George Washington ate or slept at some of the places here!

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Annapolis, Maryland. A sunny day, a water taxi ride, and perfect lunch!

Annapolis, Maryland. A sunny day, a water taxi ride, and perfect lunch!

Check out the colonial history, vintage shops, and delicious seafood in Maryland's capital | Washingtonian

Check out the colonial history, vintage shops, and delicious seafood in Maryland's capital | Washingtonian

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The best restaurants, bakeries & seafood shacks in Annapolis... sure to please even the pickiest foodie!

The best restaurants, bakeries & seafood shacks in Annapolis... sure to please even the pickiest foodie!

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An Annapolis Maryland day trip or overnight delivers interesting history, delicious food, quaint shops, and plenty of ways to get out on the water.

An Annapolis Maryland day trip or overnight delivers interesting history, delicious food, quaint shops, and plenty of ways to get out on the water.

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Whether they have over-the-top American charm (we're looking at you, Woodstock, Vermont) or proximity to some of the loveliest landscapes on earth (hello, Big Sur), these towns are worth a stopover. And, since they are all on the smaller side—all are home to fewer than 130,000 people, and most far less—you can experience their culture and beauty like a local.

Whether they have over-the-top American charm (we're looking at you, Woodstock, Vermont) or proximity to some of the loveliest landscapes on earth (hello, Big Sur), these towns are worth a stopover. And, since they are all on the smaller side—all are home to fewer than 130,000 people, and most far less—you can experience their culture and beauty like a local.

101 Day Trips in Maryland - All Within 3 hours of Annapolis, MD! | Macaroni Kid

101 Day Trips in Maryland - All Within 3 hours of Annapolis, MD! | Macaroni Kid

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