Authentic Journeys on the Bay: The Heart of the Chesapeake

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The Maryland Inn in Historic Annapolis

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Annapolis Maryland from Annapolis Harbor

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Crabs at Cantler’s Riverside Inn

Start your day with the film “Annapolis: An American Story” at the Museum of Historic Annapolis
Take the museum’s self-guided tour of the historic city, including stops at William Paca House & Garden, Brice House and Hogshead
Time-travel with optional interior visits to one or more of the historic sites
For lunch, dine on a Maryland crab cake washed down with a “colossal” milkshake at the iconic Chick & Ruth’s Delly
Stroll, browse and shop the boutiques and find a nautical-themed souvenir on the carefully restored red brick streets of downtown Annapolis
Catch a genuine dock-to-table dinner experience at Cantler’s Riverside Inn traditional crab shack
Reflect on your journey through nearly 400 years of history and catch some Z’s at the Maryland Inn of the Historic Inns of Annapolis

Annapolis Maritime Museum

The Skipjack Wilma Lee

Thomas Point Shoal Lighthouse Tours

Greet the day at the Maryland Inn
Have a breakfast crepe with a cafe au lait at Cafe Normandie
Set sail on a skipjack for a Chesapeake Bay Storyteller tour aboard the Skipjack Wilma Lee OR ride the waves to visit the historic Thomas Point Shoal Lighthouse
Relax with local fishermen and sailors over lunch at the Boatyard Bar & Grille
OR pick up a seafood platter at Wild Country Seafood and dine at outdoor picnic tables, just steps away from the Annapolis Maritime Museum
Explore maritime heritage and the Bay’s ecology at the Annapolis Maritime Museum, housed in the former McNasby’s Oyster Company
Raise a pint in the airy taproom at Forward Brewing
Enjoy dinner overlooking Spa Creek at Carol’s Creek Cafe
Rest up for more adventure at the Maryland Inn

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St. Michaels Harbor

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Noon Formation at the U.S. Naval Academy

Lyon Distilling

Lyon Distilling in St. Michaels

Wake up in the historic and charming Maryland Inn
Enjoy breakfast at the Iron Rooster for some Southern-style down-home cookin’
Get a behind-the-scenes tour of the U.S. Naval Academy
Drive to St. Michaels (1 hour drive)
Have lunch on the water at Foxy’s Harbor Grille
Shop for gifts and souvenirs and browse art galleries in this quaint coastal town
Tour the St. Michael’s Winery, Bordeleau Winery, Lyon Distilling or Eastern Shore Brewing
Enjoy Italian fare in the lively and vibrant Limoncello Restaurant and Wine Bar
Spend the night in the 18th century, enhanced with modern comforts at the Log Canoe Inn

Chesapeake Bay Maritime Museum

Hooper Strait Lighthouse at the Chesapeake Bay Maritime Museum

St. Michaels Marina

Chesapeake Bay Maritime Museum

Guests hold a Blue Crab at the Chesapeake Bay Maritime Museum

Wake up to a wonderful water view at the Log Canoe Inn
Grab a quick breakfast at The Blue Crab coffee shop
Visit the Chesapeake Bay Maritime Museum, a Chesapeake Bay Storyteller
While at the museum, tour the Hoopers Island Lighthouse and take a Miles River Cruise on the Winnie Estelle buyboat
Relax over lunch with locally caught seafood at Blu Miles Restaurant
Take a mini road trip along the Frederick Douglass Driving tour with stops at sites in St. Michael’s and Tilghman Island
OR explore the life of a waterman at the Tilghman Watermen’s Museum
Take in a glorious Bay sunset on Tilghman Island
Enjoy a dinner of seafood fresh from Tilghman Island’s fishing docks at Tickler’s Crab Shack at the Wylder Hotel
Stay the night at the Wylder Hotel