Home Tour Ideas Itineraries Itinerary: Annapolis, Maryland

Itinerary: Annapolis, Maryland

March 11, 2026

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WALK THROUGH HISTORY

Step back in time at Historic London Town & Gardens, where a once-bustling Colonial port town has been brought back to life. Stroll through reconstructed buildings, and wander 10 acres of woodland and gardens. For a deeper dive into the city’s story, join a period-attired guide from Watermark, whose walking tours bring Annapolis’ Revolutionary and maritime history to life—from the Maryland State House to the U.S. Naval Academy, where tomorrow’s leaders begin their service.

After dark, uncover a more mysterious past with Annapolis Ghost Tours & Crawls. Led by spirited guides, these tours mix haunted history with a taste of local nightlife, featuring eerie tales and moonlit strolls.

GET ON THE WATER

Life in Annapolis flows with the tides. Hire a boat from Annapolis Fishing Charters for a classic Chesapeake Bay outing. Or, try light-tackle action with Hookset Guide Service, where anglers enjoy a hands-on experience just south of the city. Prefer to stay dry? Watch the sails drift by from the docks, or take a scenic harbor cruise. However you explore it, the bay is always the main attraction.

TASTE THE BAY

Dining is a celebration of land and sea. Sample legendary crab cakes at Boatyard Bar & Grill, a local favorite known for fresh-caught seafood and “all killer, no filler” crab cakes. O’Brien’s Oyster Bar & Seafood Tavern serves up oysters, shrimp, and house-made specialties in a warm tavern setting, while Iron Rooster puts a creative twist on comfort food from breakfast through late night.

Beyond downtown, raise a glass at Great Frogs Winery, where rustic charm meets Chesapeake terroir, or visit The Vineyards at Dodon, a sustainable estate where tastings pair perfectly with the peaceful countryside. If craft beer is more your style, Forward Brewing in Annapolis’ Eastport neighborhood offers inventive, small-batch brews with a welcoming community vibe.