Destinations to Explore While Sailing on the Chesapeake

Boats - SailingOne of the best parts of having your own boat is being able to explore unique areas with your family. Chesapeake Bay features a variety of must-see attractions, so narrowing them down for your boating expedition can be difficult! Here are a few destinations to explore before you put your boat into boat storage at a marina in Annapolis.

Fort McHenry

Do you want to explore history as you tour Chesapeake Bay? If so, be sure to stop by Fort McHenry. This star-shaped fort, which is best known as the location of the Battle of Baltimore in the War of 1812, offers a Visitor Center where you can learn all about the fort’s history and significance. You can also walk around the fort and explore the barracks. Flag Change Programs occur twice daily, and are sure to entertain visitors of all ages.

Hart-Miller Island

This island, accessible by personal boat, offers beautiful beaches for your family to explore. If you have time, you can even plan a camping trip on the island. Bicycle rentals are also available, so you can easily explore the island after you dock your boat. Swimming, picnicking, and wildlife viewing are other fun activities that you can enjoy during your visit to Hart-Miller Island.

Calvert Cliffs

As your family boats through Chesapeake Bay, be sure to schedule a stop at Calvert Cliffs State Park. This day-use park features beautiful sandy cliffs along its shoreline. The sea continuously erodes these cliffs, revealing prehistoric fossils. During your visit, your family can explore nature trails, swim at the beach, or play at the recycled tire playground.


If you are ready to explore a new city while boating in Chesapeake Bay, be sure to stop at Annapolis. You can store your boat at a transient boat slip in a marina, and spend the day shopping, dining at fine restaurants, and taking in the unique culture of this historic city. When you visit, be sure to check out the galleries in the Arts District and schedule a tour at the United States Naval Academy.


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