Sail the Chesapeake, then crack a bushel
Annapolis, MD anchors a bachelor party weekend built around 12 curated venues including Middleton Tavern. The nearest major airport, BWI, is 30 minutes from the core.
sunset cruise • 2 hr
74' schooner into the Chesapeake with cocktails aboard
boat cruise • 3 hr
Take the helm in the sailing capital of the U.S.
food tour • 2.5 hr
Mallets, Old Bay, and a bushel at a creekside crab house
walking tour • 2 hr
Colonial streets + the USNA yard
bar • balanced • $$
250-year-old waterfront tavern with nightly live music + oyster bar
bar • balanced • $$
Painkillers on the City Dock waterfront deck
bar • balanced • $$
West Street tavern with live bands, trivia, and karaoke
Crab house • $$$ • Best for: group-dinner
The definitive Annapolis crab pick since 1974, on Mill Creek
Chesapeake seafood • $$$ • Best for: dinner
Spa Creek views of the Bay Bridge + city skyline
Seafood / raw bar • $$ • Best for: lunch
Award-winning crab cakes + a great raw bar
hotel • Max 2 guests
Only hotel directly on the harbor at City Dock
airbnb • Max 10 guests
Walk-to-the-dock 4BR with a creek view
house • Max 14 guests
Dock and a bridge walk to the historic district
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