Best 241 things to do in Annapolis, MD

Discover Annapolis's Navy culture, history, and Chesapeake character

Bring your own drinks and cruise Annapolis on a private tiki boat for 8–16

Cruise the South River with spacious seating, storage, and an onboard toilet

Take a versatile 19-foot boat out for watersports, dining stops, and easy cruising

Cruise or fish aboard a stable 23-foot center console

Relax and cruise the South River on a spacious pontoon

Private evening on the water with sunset views from the South River

Cruise Chesapeake waterways to Annapolis landmarks with a captain

Cruise Chesapeake Bay coves and historic waterfronts en route to Galesville

Cruise Chesapeake Bay to Rock Hall with time to explore ashore

Cruise the Chesapeake Bay to explore historic St. Michaels by boat

See Chesapeake landmarks and explore historic Oxford by boat

Cruise Chesapeake Bay aboard a 60-foot Viking with captain, crew and fuel included

Cruise the South River with 250 HP power and an onboard toilet

Choose your Gettysburg Licensed Battlefield Guide for a private 2–3 hour car tour

Cruise Chesapeake Bay with your own drinks, music, and flexible stops

Private cruising with your playlist, swim stops, and bring-your-own drinks

Release stress with a fun shared Rage Room session

Break a sweat in a color-lit rage room with your crew

Take aim during a group axe-throwing session

Make glowing neon art in a blacklight room

Break glass and blow off steam in a hands-on rage room session

Sail the Miles River with room to relax aboard Epiphany

Propose aboard a private yacht with champagne and a harbor sail