things to do in Grasonville, MD

Sail a Historic 1935 Ketch on the Miles River

Discover the shoreline stories behind St. Michaels

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

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

Honor your loved one with a private farewell shaped around your wishes

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

Pair colonial history with a pub meal

Learn to glide above the water with step-by-step instruction

Rent two boats at once and receive a 10% discount

Explore Maryland's Eastern Shore aboard a 1942 training aircraft

Explore St. Michaels after dark through ghost stories and maritime history

Anchor in protected waters for a gentle paddleboard yoga flow

Sample Six Curated Wines While Sailing Chesapeake Bay

Pair sunset views with your own music and drinks

Taste your way through Annapolis history, one restaurant stop at a time

Step inside one of Dorchester County's five intact Georgian historic homes

Set your own course for waterfront stops or a laid-back day at anchor

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

Discover colonial life and the landmarks that shaped Annapolis

Take to the water in a kayak for one

Cruise quietly with your own food, drinks, and music

See Maryland's Eastern Shore from between the wings of a vintage biplane

Walk Easton's haunted past through its notorious Tragedy Triangle

Build paddleboarding skills with certified coaches, then paddle at your own pace