Five-Night Itinerary*:

Day One: Guests can board Arabella along the vibrant Annapolis, (the first capital of the US), waterfront at 4pm. Famous for its stunning period architecture and lively seaport culture, Annapolis is a mecca for history buffs and adventure seekers. Check out the scene at the US Naval Academy just steps from the dock, then discover the sights, epicurean adventures and charming stops that this city has to offer. After a “welcome aboard” cocktails on Arabella’s aft deck, don’t forget to sample the wealth of dining opportunities Annapolis is so famous for.

Day Two: This morning we set sail into the middle Chesapeake, whose sheltered waters and bountiful fisheries of America’s greatest estuary have attracted people for centuries. As we cruise past wooded shores, you’ll see crabbers hauling their catch, sailing oyster dredges dragging the shallows for these succulent shellfish, while sealife of all types teem about. Our sail today brings us to the mouth of the Choptank River , off which branches the Tred Avon River - on which we find the port of Oxford. This tidy village is full of history and charm, surrounded by the sparkling inhabited islands and creeks. We'll launch our fleet of sea kayaks for exploring the marshes upstream, or you can rent a bike and take a short trip across the river to Bellevue, the oldest privately operated ferry service in the United States (since 1683), and ride along the quiet wooded lanes. Dinner will be at the lovely and historic Robert Morris Inn (included).

Day Three: Back out into the Bay today for a brisk sail down to Solomons, at the mouth of the Patuxet River on the west shore of the Bay. This delightful port offers many attractions, including a restored 1934 seafood packing house, but a short cruise upriver shows a very different culture than seen so far. Nestled amongst the heavily treed bluffs along the river are plantations and manor houses that are survivors of the Antebellum South. Many of these are now restored and open to the public. Our visit to this unique area would not be complete, however, without a visit to the Calvert Marine Museum, where we can learn more about the ecology and natural resources of the Bay. Dinner is on your own tonight in town.

Day Four: Sunrise finds up slipping past the red clay Calvert Cliffs, remnants of an ancient seabed and laden with fossils. The crew shakes the morning dew from the sails, we then direct our course northwest back to the Maryland Eastern Shore. By lunchtime, we're dropping anchor off the Eastern Shore seaport of St. Michaels, where we'll spend the day ashore exploring this historic seaport. The Chesapeake Bay Maritime Museum is a must-see, with a collection of 85 vessels and the restored Hooper Strait Lighthouse on display. Take in St. Michaels bustling Main Street, with many delightful shops, while the narrow streets lined with 17th and 18th century houses make for an enjoyable stroll including the Inn at Perry Cabin that was once home to Laura Ashley, and is in the Orient Express Hotel Group. Be sure to work up an appetite, because tonight we'll be treated to a Chesapeake tradition - the Crab Feast - where we'll get to enjoy the local harvest of the sea as it's been prepared for generations (included).

Day Five: This morning we'll sail past the wooded shores of Kent Island, where we'll pass under the majestic span of the Chesapeake Bay Bridge, which has joined the Eastern and Western shore of the Bay since its construction in 1952. Our final destination is Baltimore, a city steeped in history. From Fort McHenry, home of our national anthem, looming over the Harbor, to the towering spans of the 18th Century warship USS Constellation, to the magnificent Baltimore Aquarium, the largest marine aquarium in the country, Baltimore offers something for everyone.  After an afternoon soaking up the attractions on the harborfront, we suggest venturing off to the old settlement of Fells Point. Then we will raise a final toast to fair winds and calm seas at our cocktail party on board…after which you are free to explore Baltimore's many unique restaurants for dinner.

Day Six:Our final sail down the broad waters of the Chesapeake, a cloud of canvas overhead- seabirds skimming low over the blue water, finds us sailing back into the bustling harbor of Annapolis.  After a farewell brunch, you’ll still have time to stroll the waterfront for one last look at the tranquil waters of the Chesapeake Bay.

*This is a sample itinerary. All stops are subject to the captain’s discretion and may vary due to weather or unforeseen circumstances.