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Annapolis, Maryland is many things- Maryland’s state capital and home to the United States Naval Academy, but it is most importantly known as the “Sailing Capital of the United States.” Annapolis is located on the Chesapeake Bay which happens to be the largest estuary in the United States. This estuary stretches into a total of six surrounding states allowing boat lovers near and far the opportunity to test the Bay’s waters. At Click&Boat, we have decided to look into the best sailing spots in Annapolis and around the Chesapeake Bay to inspire new adventures in such an amazing and historical area.
Situated along the Severn River, Annapolis is the ideal rendez-vous point for boaters sailing the Chesapeake Bay. Its harbor offers great shelter, with plenty of anchorages, moorings, and boatyards. With a boat rental in Annapolis, dock at the marina and visit the historic city full of lively waterfront shops, restaurants, and bars.
The sailing scene in Annapolis, Maryland thrives year-round. You will often find that on Friday nights after work, locals will board their boats and sail around the Chesapeake for the weekend. However, there are always sailing events going on as well. Every Labor Day weekend, more than 200 boats take to the water to race. And over the years, major competitions like the America’s Cup and the Volvo Ocean Race have taken place in Annapolis.
Sailing Around Annapolis…
St. Michaels
Located on the Eastern shore in the Chesapeake Bay, boaters love to visit the quiant, historic town of St. Michaels. Voted one of the “Top 10 Best Small Coastal Towns” by USA Today, St. Michaels is nothing short of exceptional dining options, boutiques, cozy B&Bs, and a beautiful harbor. A boat rental in Annapolis is the perfect opportunity to make the trip to St. Michaels and also navigate the Miles River where you may spot Ospreys and Dolphins.
Rock Hall
Rent a sailboat and sail to the so-called ‘Pearl of the Chesapeake,’ Rock Hall. This waterfront village was settled in 1706 and today has it all. You can learn about the Eastern Shore culture, spend time in nature, hiking and biking, and of course spend time out on the water, fishing and sailing. At Rock Hall, you can also take the time to relax. Dock your boat at one of the many waterfront restaurants and bars. Enjoy live music and fresh local catches like oysters, rockfish, and of course- crab!
Chestertown
From Rock Hall, sail up the Chester River and you will arrive in Chestertown. In 1706, Chestertown was the second leading port in Maryland, behind Annapolis. The merchants of the time influenced the architecture in the town. Today, you can dock your boat and explore Chestertown by foot, walking on the sidewalks of eighteenth century brick townhouses and mansions. Spend time exploring this charismatic town, visit the market, discover the local boutiques and grab an ice cream!
Chesapeake City
Sail to Chesapeake City, the “Hidden Treasure of the Chesapeake.” What was once a rowdy boom town in the 1920s, Chesapeake City is now a charming and welcoming sailing destination for boaters all over the Bay. This little town happens to be located on a working commercial canal built between the 1920s and 1940s, that helped connect Baltimore to the Delaware River. Boaters can spend time in the town’s tranquil harbor, and can discover what this quiant nineteenth century styled town has to offer.
Baltimore
From Annapolis, Maryland, you can sail to Baltimore in under seven hours, depending on conditions. Or you can also choose to find a boat rental in Baltimore and sail the area from there! Baltimore is Maryland’s biggest city and has been deemed one of America’s greatest historical destinations. This city played a major role in the defining moments of the Revolutionary War, and its port was critical for ship-building and supply-shipping for World War I and II. Today, while Baltimore holds on to its historical significance, the city offers a lot of things to do and see. You can start with visiting Baltimore’s Inner Harbor, an urban waterfront park!
We can easily say that it is hard not to fall in love with Annapolis and the Chesapeake Bay area. Be sure to check out Click&Boat’s blog on other romantic destinations to sail to in the United States.
