Charms of the Chesapeake
September 13 - 19, 2026
$3,995 /double • $5,095 /single

From colonial port towns and elegant waterfronts to wild barrier islands, this intimate journey reveals the heart and soul of the Chesapeake Bay. Explore historic Annapolis, sail aboard a classic schooner, trace the paths of Harriet Tubman and Frederick Douglass, and experience the quiet beauty of Maryland’s Eastern Shore before viewing the wild ponies of Assateague from the seas and strolling sandy beaches amidst island charm of Chincoteague.
Tour Includes
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TOUR INCLUDES
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Local home pick-up service and luggage handling
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Fully escorted by Globe Treks tour manager
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All meals, attractions, guides, and activities
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Two-night stay at the Annapolis Waterfront Hotel
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Guided tour of Maryland’s capital, including the U.S. Naval Academy and William Paca House
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Sailing adventure aboard the 75-foot schooner Woodwind
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Two-night stay at the luxurious Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina
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Guided exploration of Easton, Oxford, and Cambridge
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Visit to the Harriet Tubman Underground Railroad Visitor Center and Frederick Douglass Park
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Two-night oceanfront stay on Chincoteague Island, Virginia
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Cruise on the Assateague Explorer to view wild ponies
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Delicious regional cuisine, from waterfront seafood feasts to elegant Chesapeake dining
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Deluxe 14-passenger motorcoach with extra legroom, refreshments, and door-to-door pickup
