Best 254 things to do in Chesapeake Beach, MD

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

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

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

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

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

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

Cruise the Patuxent River on a 20-foot pontoon

Cruise the Patuxent River for fishing, swimming and water sports

Cruise the Patuxent River at your own pace by pontoon

Bottom-fish with room to cast on a 16-angler boat

Private bay fishing with gear, bait, and fish filleting included

Private fishing time to follow seasonal bites farther from shore

Walk Easton's haunted past through its notorious Tragedy Triangle

Soak in Solomons Harbor views with a weather-permitting ride on the Patuxent River

Hear true local ghost stories on a nighttime walk through historic Cambridge

Paddle National Harbor in a beginner-friendly sit-on-top kayak