Cruising the Chesapeake Bay
From Baltimore, MD to Cape Charles, VA
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The Chesapeake Bay is a spectacular North American cruising ground that was shaped by a big bang 35 million years ago when a comet or asteroid slammed into what is now the lower tip of the Delmarva Peninsula. That impact left a crater 55 miles wide that became a convenient depression for rivers to flow into as the glaciers of the last Ice Age melted some 10,000 years ago. The Algonquian word Chesepiooc, meaning “at a big river” became the source of the name for the estuary now called the Chesapeake.The Chesapeake Bay spans more than 64,000 square miles and is home to 150 major rivers and streams. A true boater’s playground, you will find everything you need. From live music and great tiki bars, to cruising with the kiddos, there’s no shortage of fantastic Chesapeake Bay marinas and fun activities here. Below please find a sample itinerary, complete with marina information, deals and discounts.

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Harbor East Marina
305-398-6800
Miami Beach, FL
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Annapolis Yacht Basin
305-398-6800
Miami Beach, FL
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Haven Harbour Marina
305-398-6800
Miami Beach, FL
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St. Michaels Marina, LLC
305-398-6800
Miami Beach, FL
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Safe Harbor Oxford
305-398-6800
Miami Beach, FL
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Safe Harbor Zahniser’s
305-398-6800
Miami Beach, FL
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Parks Marina
305-398-6800
Miami Beach, FL
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The Tides Marina
305-398-6800
Miami Beach, FL
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Cape Charles Yacht Center
305-398-6800
Miami Beach, FL

Cruising the Chesapeake Bay

From Baltimore, MD to Cape Charles, VA

Cruise Length
TOTAL
Miles

The Chesapeake Bay is a spectacular North American cruising ground that was shaped by a big bang 35 million years ago when a comet or asteroid slammed into what is now the lower tip of the Delmarva Peninsula. That impact left a crater 55 miles wide that became a convenient depression for rivers to flow into as the glaciers of the last Ice Age melted some 10,000 years ago. The Algonquian word Chesepiooc, meaning “at a big river” became the source of the name for the estuary now called the Chesapeake.The Chesapeake Bay spans more than 64,000 square miles and is home to 150 major rivers and streams. A true boater’s playground, you will find everything you need. From live music and great tiki bars, to cruising with the kiddos, there’s no shortage of fantastic Chesapeake Bay marinas and fun activities here. Below please find a sample itinerary, complete with marina information, deals and discounts.

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Harbor East Marina
410-625-1700
Baltimore, MD

The best of the Baltimore is located just steps off the docks at Harbor East Marina. Located in the heart of the city, the Harbor East area of Baltimore boasts 12 square blocks of fine dining restaurants, world-class hotels, hip lounges, quaint pubs, and the best of national and local shops. In addition to all that Harbor East has to offer, marina guests can walk to all the major attractions at the Inner Harbor, Fell’s Point and Little Italy including the National Aquarium and the Maryland Science Center. A quick cab ride will take sports fans to Oriole Park at Camden Yards and M&T Bank Stadium. From Harbor East Marina, guests are also just a short walk away from all of the major attractions at the Inner Harbor, Fell’s Point and Little Italy. Nestled in the center of it all, Harbor East is your gateway to discovering the best of Baltimore.

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Annapolis Yacht Basin
410-263-3544 ext 101
Annapolis, MD

A walking tour of historic Annapolis, which is arrayed like spokes in a wheel from the Maryland State House, will delight architectural aficionados. Examples of Federal, Italianate, Georgian, Queen Anne and Greek Revival styles from the colonial period through the early 1900s abound. Good provisioning near the marina is hard to find. The locals’ favorite, Graul’s Market, with excellent produce, meat and fish is a mile and a half away. However, the marina has rental car and taxi services available to help stock up at Trader Joe’s, Whole Foods and Fresh Market. The Annapolis Yacht Basin has fuel and Annapolis Harbor Boat Yard is a full service maintenance yard that is conveniently located on Spa Creek near the historic district.

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Haven Harbour Marina
(410) 778-6697
Rock Hall, MD

Rock Hall has everything a boater could wish for from first class service/maintenance facilities, restaurants, a grocery store, and fun events all accessible by bike, on foot, or by the great trolley system that connects all of the marinas. Rock Hall has many antiques and crafts stores including America's Past Antiques, Fishbone's Antiques, Rock Hall Gallery and the Artists of Rock Hall Gallery. You will also find gift stores, jewelry, clothing and accessories including Smilin Jake's Casual Apparel on Main Street. Don't miss Pirates and Wenches weekend aka Fantasy Weekend, which includes a decorated dinghy flotilla and kayak races, Caribbean beach party, treasure hunts, entertainment, contests and games for landlubbers and boaters alike. When looking for a place to grab a bite select from Bay Wolf Restaurant, Harbor Shack with live music on Saturday nights, and Waterman's Crabhouse.

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St. Michaels Marina, LLC
410-745-2400
St. Michaels, MD

For boaters, the focus of this Eastern Shore town is the Chesapeake Bay Maritime Museum with exhibits, restored vessels and hands-on boatbuilding workshops. It is where James Michener did his primary research for his best selling novel, “Chesapeake,” 40 years ago. The picturesque streets of St. Michaels are perfect to stroll along while looking for lunch or dinner. Topping off provisions is easily done within walking distance of the marina at Olivins, a gourmet grocery, or Acme supermarket. Fuel is available at St. Michaels Marina. Higgin’s Yacht Yard is the last full-service boatyard in existence in town.

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Safe Harbor Oxford
410-226-5101
Oxford, MD

Oxford’s main attraction is the town itself. It is one of the oldest towns in Maryland, officially founded in 1683. The charming, tree-lined village is a quiet antidote to the hustle and bustle of city life. The Oxford Market, a convenience store, is the only spot in town to buy any essentials for provisioning. If you need fresh fish and seafood, watch for the watermen when they bring their catch in early in the day. The marina is also a full-service boat yard, with gas and diesel available. Hinckley Yacht Services also has a full-service yard in town. Both Brewer and Hinckley provide quality work and craftsmanship.

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Safe Harbor Zahniser’s
410-326-2166
Solomons, MD

Zahniser's Yachting Center is one of the most comprehensive marine facilities on the Chesapeake Bay; Located in the town center of Solomons Island, Maryland, Zahniser's is a full-service marina that blends the beauty of a pristine yacht club and the technical expertise of an award winning repair yard. It's the perfect starting point to enjoy the historic village of Solomons Island, either on foot or by bicycle. A destination not to miss - unwind, relax, and enjoy! The marina also has: WiFi, Courtesy Bicycles, a Recycling Center, a Sail Loft & Canvas Shop, Marine Surveyor, Sailing School & Yacht Charters. The marina can also haul vessels up to 70 tons.

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Parks Marina
757-891-2581
Tangier, VA

Tangier Island is the home of working watermen who get up well before dawn to get their boats ready for crabbing and oystering. The island is most well known for its soft shell crab, for which it claims to be the world capital. With a total population of about 700, most who live there can trace their ancestry back to a handful of families. The small settlement is unique to the Chesapeake and wandering its lanes is the ideal way to pass the time after lunch or dinner at one of the two local restaurants. And, of course, order soft shell crab and crab cakes. Parks Marina is just across the harbor channel from the many crabbing shacks built on stilts along the shore. The marina is owned and operated by 85-year-old Milton Parks, and is a simple affair with fixed docks, pilings and a faded signboard. Milton gladly offers advice on how to dock in the strong current and, once your boat is tied up, he will spin many a story of the island’s inhabitants and history. Daley & Sons is the only grocery store on the island. There are no repair or fueling services for recreational boaters on Tangier Island, but in a pinch a waterman may be able to provide some assistance.

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The Tides Marina
804-438-4418
Irvington, VA

The Tides Inn Marina, 11 miles from Windmill Point on Carter’s Creek, is one of the most luxurious marinas on the Chesapeake Bay. Once docked on their private peninsula, you will have access to complimentary laundry, excellent shower and bath facilities, van and water taxi services, dining and lounges. The resort has a variety of dining options to choose from, all with their own unique style. Relax and recharge with therapeutic treatments at the Journey Spa, or play golf at the Golden Eagle Golf Course. There is always an array of outdoor activities available including tennis, kayaking, croquet, and complimentary bicycles.

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Cape Charles Yacht Center
757-331-3100
Cape Charles, VA

Some cruisers who have visited this revived, historic railroad town on Virginia’s Eastern Shore say it’s one of the Mid-Atlantic’s best-kept secrets. Life is easy in this inviting bayside town, with bikes and golf carts sufficing for transportation and menus heavy with local seafood. With most of its structures built between 1885 and 1920, Cape Charles has one of the largest concentrations of restored late-Victorian and turn-of-the-century buildings on the East Coast. Many of these beautiful structures are now transformed into bed and breakfasts, galleries and specialty boutiques. The Gull Hammock Gourmet Market and Drizzles are two high-quality groceries for additional provisioning. They are adjacent to the historic district and conveniently located on your way back from the beach to your boat. At Cape Charles Yacht Center, yachts have full access to nearby Bay Creek Resort, featuring a Beach Club pool as well as two signature golf courses designed by Jack Nicklaus and Arnold Palmer.

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