Travel Destinations

Island Hopping: The Chesapeake Bay Islands


The waters of the Chesapeake Bay resonate with a kind of welcoming quiet, as this part of the country is perhaps one of the more laid back with views that are as tranquil as the people are friendly. It's not too far from a number of metropolitan areas, yet these cruising grounds will put you a million miles away mentally. The bay, with more than 64,000 square miles, is a big place for cruisers to explore, but if you're inching your way around its pretty shorelines, consider checking out the following islands.

Kent Island, Maryland

One of the largest islands on the bay, it's located at one of the narrowest points of the main waterway, which is spanned by the Chesapeake Bay Bridge. The island sits at the eastern end of that bridge, which could be why it gets its share of tourists, although there's a good chance visitors come here to indulge in the incredible seafood and absorb the area's history. Kent Island was established in 1631, when William Claiborne of Jamestown set up a trading post on what would become the oldest English settlement in the state. Stevensville is the historic downtown area, with restored buildings that preserve its 19th-century feel. There's shopping and dining too, plus the award-wining Terrapin Nature Park. For the active set, there are public piers for fishing and crabbing, kayak rentals and a nice, paved biking trail that winds over the island.


  • Castle Harbor Marina (410-643-5599) A full-service facility with 347 slips, ship store, bathhouses, swimming pool, hot tub, children's wading pool and fuel dock.
  • Bay Bridge Marina (410-643-3162) Located at the base of the Bay Bridge, accommodating vessels up to 130 feet.
  • Queen Anne Marina (410-643-2021) A full service marina offering fuel, ship store, travel lift and catering services from Silver Swan Bayside.


Cobb Island, Maryland

Located at the junction of the Potomac and Wicomico rivers, it's separated from the mainland by Neale Sound and connected by a fixed bridge. Cobb Island is a small community that's mainly residential, but it's easily walkable and very scenic, which is the draw for many cruisers. In addition, there are still a number of watermen working out of the island, and their boats, along with pleasure craft, are lovely to see tied up on Neale Sound. It's a great place to stop for lunch or dinner when traveling from Southern Maryland or the northern neck of Virginia, as there are a few fine seafood restaurants serving the specialties of the area, such as rockfish, steamed crabs and oysters and fresh crab cakes. There's an ice cream parlor, too. If you play golf, there's an 18-hole course that's open to the public at Swan Point Yacht and Country Club, which is just north of Cobb Island.


  • Captain John's Crab House (301-259-2315), just across the Neale Sound from Cobb Island. The marina offers transient dockage for boats up to 42 feet along with free pump out, dockside gasoline, bait and tackle and, of course, the Crab House Restaurant.

Tilghman Island, Maryland

Like Kent Island, it too is located on Maryland's Eastern Shore, only Tilghman is farther south and separated from the mainland by Knapps Narrows. It's in the mid-Chesapeake Bay region and very close to the much-loved port of St. Michaels, along with Oxford and Easton. It's a true waterman's village and home to the last sailing skipjack workboat fleet on Chesapeake Bay. (That fleet is on display at Dogwood Harbor.) Among the fun things to do here are charter a boat with a professional fishing crew or arrange for tours around Sharps Island Light, located off the tip of the island, and to Poplar Island, which served as a campsite for British warships during the War of 1812. If you prefer to explore Tilghman by foot, take a long and leisurely nature walk. You could see eagles, egrets and herons, and Monarch butterflies make stops to the island in late summer.


  • Knapps Narrows Marina & Inn (410-886-2720), adjacent to the Knapps Narrows Bridge, is both a full-service marina and boatyard, as it has a 35-ton lift and work shed. Transient slips are available on the 1,000-foot floating dock.
  • Tilghman Island Inn & Marina (410-886-2141), offers dock and dine at their first-class restaurant with amazing water views and outside dining.

Tangier Island, Virginia

Located in a part of the bay called the Lower Eastern Shore, Tangier is made up of small islands divided by marshes and small tidal streams. Tangier Island is a bit isolated, as its 12 miles from the mainland and separated by the expanse of Tangier Sound. Accessible only by boat or airplane, it's about one mile wide and three miles long, with only about 800 residents, many of whom are descendants of the original settlers and make a living crabbing and oystering. There are limited amenities here (a few restaurants, a hardware and grocery store among them), but the casual atmosphere can improve anyone's blood pressure. Most people get around the island by golf cart, bike or moped, and in the summer, boaters who tie up like to spend the afternoon exploring. Stop by the Tangier Island History Museum and ask about the free kayaks and canoes available for self-guided tours of the water trails around the island.


  • Parks Marina (757-891-2581) is the only marina on this island, and while this deepwater facility is not fancy, it's welcoming. You can dock for a brief stay or overnight, and showers are on-site. Boats up to 100 feet have berthed here. Try to arrive at slack tide for easy docking.

Afternoon Delight

There are countless places to tie up for the night on Chesapeake Bay, and then there are locations that are just right for an afternoon on the hook. Two of the most popular are Hart-Miller and Dobbins islands in Maryland. There are no docks on these islands, but there's plenty of natural beauty, and in the peak summer season, big raft-ups make for great socializing and people watching. Hart-Miller, a 1,100-acre island located just north of the North Patapsco River and south of Middle River, is one of the most popular anchorages on the bay. The island is part of a state park, with camping facilities, a ranger station and an observation tower. When you're not joining in on a game of water football, you can walk the 3,000-foot beach. There's safe mooring on the western shore, where you can hike, picnic, fish and bird watch. Pretty Dobbins Island, with its tree-covered, caramel colored bluffs, is located in the Magothy River adjacent to Pasadena, Md. Thanks to a deep and well protected anchorage, it draws big crowds in the summer. It's a pretty place, but it's also party central, at least on weekends. Note, however, that the beach is not a public playground. Boaters have to restrict themselves to the sliver of sand between the river and the mean high water line, which marks the division between private and public property.

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