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Chesapeake Bay & Eastern Shore

Savor the Local Specialties – Blue Crabs and Oysters Freshly Plucked From the Largest Estuary in the U.S.

Maryland's Yachting Paradise

 Nestled between neighboring states midpoint on the eastern seaboard, the State of Maryland is not only central to national history, it's heart and home to the Chesapeake Bay, the largest estuary in the United States and one of the most scenic waterways in the world. Known for its captivating beauty, a Chesapeake Bay yacht charter reveals the visual breadth in the words, “Heaven and earth have never agreed better to frame a place for man's habitation,” written in the 1600's by English explorer, Captain John Smith while mapping the mighty Chesapeake.

Your luxurious Chesapeake Bay yacht charter will take you into a seaway of over 11,000 miles of shoreline weaving into secluded inlets, gentle coves, quiet ports and bustling harbors. This spectacular yachting journey on 200-miles of sheltered water is one rich with lush vegetation, prolific wildlife and plentiful sightseeing activities.

Views from your sensational Chesapeake Bay sailing charters offer glimpses of the Great Blue Heron wading in the open waters of wetlands and bright-colored Kingfishers flying low as they hunt for fish. From your Chesapeake Bay sailing charters, watch as osprey, commonly referred to as the Sea Hawk or Fish Hawk, soar gracefully over the shores and dive headlong into the waters to grab their prey, while possums, squirrels and rabbits take leave in the cordgrass and wildflowers of the salt marshes.

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Yachting Seaports Along a Chesapeake Bay Yacht Charter

Along with a wealth of natural treasures, your sublime Chesapeake Bay yacht charter offers anchorages in fascinating locales that will make your passage even more fruitful. Annapolis, Maryland's beautiful capitol city, is home to the distinguished U.S. Naval Academy. Be sure and visit the historic Maryland State House, wander through the cobbled streets, and stop in at Chick & Ruth's Deli, a landmark diner and local favorite for delicious crab cakes, piled-high sandwiches, and over 24 varieties of homemade pies daily. Setting sail from Annapolis, yacht charters will have you tacking across the bay in search of the most idyllic cove.

On your our Chesapeake Bay sailing charter, a trip to St. Michaels is a must - an enchanting seaside village that evokes the sense of being swept back in time. Popular for shoppers who delight in unique and charming boutiques, crab lovers seeking to savor the freshest local fare and history buffs who come to see the Chesapeake Bay Maritime Museum's magnificent display of restored boats.

Heading farther south, your luxury you can moor at Solomon's Island, a quaint seafaring town at the mouth of the Patuxent River. Against picturesque scenery, The Drum Point Lighthouse, in classic, cottage-style, welcomes guests to climb the steps and survey the landscape from above. Afterward, take a relaxing walk on the wooden boardwalk leading to The Calvert Marine Museum, where exhibits on the history and culture of Southern Maryland holds visitor's attention for hours.

Other southern ports of interest include Tilghman Island, Oxford and Cambridge, while Annapolis yacht charters voyages to the northern routes of The Chesapeake explore Rock Hall, Chestertown, Georgetown and of primary interest, the Baltimore Harbor.

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Luxury Yacht Charters to Baltimore's Inner Harbor

No Chesapeake Bay yacht charter journey would be complete without time spent in the remarkable city of Baltimore and its bustling Inner Harbor. Host to outstanding cultural attractions, exceptional dining and phenomenal views of this notable seaport, you can tour the National Aquarium or The Maryland Science Center and then indulge your taste buds in a one-of-a-kind culinary experience of Maryland-style, jumbo lump crab cakes at Phillips Seafood, one of Baltimore's best-loved restaurants.

Top off the day at Fort McHenry, a cherished National Monument and inspiration for Frances Scott Key's anthem, “The Star-Spangled Banner,” which honors the valiantly successful defense against British attack during the War of 1812.

From Annapolis, yacht charters will whisk you away on a glorious excursion into the heart of yachting luxury, outstanding coastal beauty and impressive American history, for an exciting and poignantly memorable voyage of discovery.

Local Island Scenes