Known as the sailing capital of the United States, Annapolis sits at the mouth of the Severn River off the Chesapeake Bay with a beautiful view of the Bay Bridge. As you cruise into the harbor, you are welcomed by the U.S. Naval Academy seawall on your starboard and a skyline of church steeples and historic landmarks at your bow. Once you shake out your sea legs and walk the brick and cobblestone streets, you see midship-men strolling around donning their brass, local boutiques touting their wares and restaurants serving fresh seafood.
The town is filled with history and Maryland pride dating back to 1649. Not only is it the state capital, it’s engraved with plenty of maritime traditions. Annapolis hosts the U.S. Sailboat and Powerboat Shows. The community also gathers for the spring Sock Burning to celebrate the start of the boating season by tossing their socks into a bonfire and slipping on sailing shoes.
During your visit, stop by the Annapolis Maritime Museum to learn about the town’s rich nautical past and contributions to the boating industry.
The town might be small but it offers tons of activities to keep you busy! Capital SUP offers standup paddleboard lessons and even paddleboard yoga if you are a pro. Interested in learning about Annapolis’s history? Check out Watermark’s walking tours.
If you really want to feel like a local, walk across the bridge over Spa Creek and attend Eastport-A-Rockin. It’s the home-grown music festival with local vendors scattered throughout the Eastport neighborhood. Another special event that attracts crowds is the Annapolis Film Festival, which showcases more than 70 proclaimed films over four days.
WHERE TO DOCK
Annapolis Town Dock
From your boat, you will experience the hustle and bustle of downtown Annapolis while enjoying panoramic views of the city.
Annapolis City Marina
This convenient location provides you with the liveliness of downtown Annapolis and the funky vibe
Annapolis Yacht Basin
(410-263-3544, ext. 101)
A few steps from the center of the yachting community, the marina is neighbored on one side by the Annapolis Yacht Club and on the other by the Marriott Hotel.
WHERE TO DINE
McGarvey’s Saloon & Oyster Bar
Long-standing tavern offering dozens of craft beers plus a raw bar and pub menu. It’s a local favorite for oysters and crab dip.
Boatyard Bar & Grill
A nautical-themed watering hole for crabs, oysters and other seafood, plus burgers and pizza.
For fine dining, this venerable chophouse for prime cuts offers a lengthy wine list, retro booths and subdued lighting.
Jimmy Cantler’s Riverside Inn
Grab a seat at a picnic table on the deck overlooking Mill Creek and enjoy a traditional Maryland feast of hot steamed crabs.