Best 57 things to do in Princess Anne, MD

Canopy-covered river cruising with drinks, snacks, and friends

Hear Ocean City ghost stories on a guided historic district walk

Walk St. Michaels at night and hear tales of the spirits of rowdy women

Walk Berlin, MD at night and hear local ghost stories and legends

Walk Cambridge’s Haunted High Street on a 12-stop ghost tour

Cruise Ocean City’s bays at sunset with ghost stories and local lore

Walk Princess Anne after dark and hear the town’s most disturbing ghost stories

Walk with a storyteller through Pocomoke City and the haunted forest at night

Private river cruising for your group outing or special event

Cruise to Smith Island for a seafood feast and free time ashore

Cruise to Smith Island and explore Ewell at your own pace

Sail to Smith Island for a seafood feast and time to explore

Explore island back bays while searching for wild ponies and coastal wildlife

Explore Assateague’s back bays and search for wild ponies by boat

Ride a guided jet ski eco tour around Chincoteague and Assateague

Cruise Chincoteague Bay at sunset on a private luxury pontoon

Cruise Chincoteague Bay at sunset on a private skiff for up to 4

Be your own captain on a Landau pontoon in Chincoteague Bay

Rent a shallow-draft skiff and captain your own Chincoteague Bay day

Captain your own double-decker pontoon with a top-deck slide for your group

Paddle from Chincoteague to Assateague to look for wild ponies and lighthouse views

Cruise the back side of Assateague to spot wild ponies and coastal wildlife

Walk Chincoteague’s history and birdwatching spots with a local guide

Cruise at sunset to spot Assateague ponies and coastal wildlife