Sailing the Chesapeake Bay

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Portrayed by countless artists, writers, and sailors throughout history, the majestically enchanting Chesapeake Bay has secured a permanent spot atop the list of premiere boating and sailing destinations in the world. America’s largest estuary, the Chesapeake Bay boasts an impressive 11,684 miles of shoreline, more than the entire US has overall. 64,229 square miles, spanning six different states, means this body of water is home to endless coves, anchorages, and creeks. Its picturesque towns, impressive maritime history, and awe-inspiring landscapes leave a lasting memory for anyone that has had the privilege to sail its mighty waters.


Recreational sailors and professional competitors alike flock to the Chesapeake Bay each year to kick-back or put their skills to the test. Competitions are held year-round in all parts of the bay for all skill levels including the famed Governor’s Cup Yacht Race, the oldest and longest overnight race held by St. Mary’s College of Maryland. Other historic competitions still held annually on the Chesapeake Bay include the Great Chesapeake Bay Schooner Race, the Choptank Heritage Skipjack Race, and the Annual Skipjack Race and Festival.

If you’re looking to sail and explore the Chesapeake Bay, you’ll soon find it has an abundance of great destinations for you to visit. With a natural cruising route for discovery, it’s easy to see plenty of beautiful spots without intense planning. One of the top destinations according to experts is the Wye River, a 16-mile long tributary that runs around a 2,800-acre wildlife refuge known as Wye Island. Expect to see beautiful foliage including the largest remaining collection of old growth forest and wildlife, including bald eagles and great blue herons.

One of the most popular towns located on the Chesapeake Bay is St. Michaels, Maryland, loaded full of marinas, great food and bars, and the famous Chesapeake Bay Maritime Museum. Established in 1965, the museum is dedicated to “preserving and exploring the history, environment, and people of the entire Chesapeake Bay, with the values of relevancy, authenticity, and stewardship guiding its mission.” If you visit, make sure you check out their collection of historic Chesapeake Bay watercraft, the largest in existence, and the Hooper Strait Lighthouse. As this is a working museum, you can always drop in and watch boating restorations live right alongside the men and women working for a real taste of history. It can be rare to get such an intimate look into this art.

This mammoth body of water has been and will continue to be the home and preferred destination for many sailors, both new and old. Whether you’re looking to try sailing for the first time, are a hobbyist, or a serious competitor, the Chesapeake Bay is home to a wealth of history and natural beauty that will satisfy your every craving.

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