Sample Chesapeake Itinerary

Five-Night Itinerary


Day 1    Guests can board ARABELLA along the vibrant Annapolis waterfront in the early afternoon.  Famous for its stunning period architecture and lively seaport culture, Annapolis is a mecca for history bluffs 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” cocktail hour on Arabella’s aft deck, don’t forget to sample the wealth of dining opportunities Annapolis is so famous for.

Day 2  This morning we set sail into the upper 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 crab fisherman hauling their catch, sailing oyster dredges dragging the shallows for these succulent shellfish, while sealife of all types teem about.

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 Meritime Museum is a must-see, with a collection of 85 vessels and the restored Hooper Strait Lighthouse on display.  Cap off the day by sampling the authentic cuisine of this hidden side of Maryland.

Day 3  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 sparkling inhabited islands and creeks.  We’ll launch our fleet of sea kayaks for exploring the marshes upstream, or you can rent a bike, take a short trip across the river to Bellevue on the oldest privately operated ferry service in the United States (since 1683!), and ride along the quiet wooded lanes.  Be sure to work up an appetite, because tonight we’ll be treated to a Chesapeake tradition – the crab boil- where we’ll get to enjoy the local harvest of the sea as it’s been prepared for generations.

Day 4  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 Chesapeake Biological Laboratory, where we can learn more about the ecology and natural resources of the Bay.

Day 5  Today we’ll cross the bay and venture further up the Choptank River, to the bustling town of Cambridge.  One of the oldest towns in Maryland, Cambridge offers museums and historic homes, as well as the Brookes Barrel Company.  Here we get a chance to cruise on a traditional Chesapeake Bay skipjack, the Nathan, which serves as a sailing ambassador for the town.  Plan a walking tour, or set off on your own expedition by kayak along the peaceful riverfront.  Tonight join your shipmates at one of Cambridge’s great dining spots to recap the highlights of your cruise.

Day 6  Our final sail up 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 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. 


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