Annapolis, Maryland

At the literal and metaphorical center of Chesapeake Bay lies Annapolis. It’s home to nearly a dozen marinas that all put you in the center of the city, but the Annapolis Yacht Basin places you directly in the aorta. Depending on which slip you get, you may be only feet away from bustling Main Street. High-speed fuel pumps, 
Wi-Fi access and immaculate amenities make for a comfortable extended stay. 

There are plenty of dining options within walking distance. Café Normandie and Luna Blu Ristorante Italiano have both received high praise for their ability to deliver both European ambience and flavor. If a bucket of blue crab claws and cold beer is more your speed, you’ve come to the right place. Cantler’s Riverside Inn and Mike’s Crab House are popular local spots. 

For those who arrive in this port under power, the schooner Woodwind cruises provide a breath of fresh air while you pass a backdrop of lighthouses and the setting sun. There are always cultural offerings and, of course, the U.S. Naval Academy.

Annapolis has managed to blend 21st century amenities with 17th century charm.

To read an explanation of the beauty of boating in Annapolis and the Chesapeake in the fall by George Sass Sr., click here.