Water Activities in Annapolis, MD

Sail a Historic 1935 Ketch on the Miles River

Discover the shoreline stories behind St. Michaels

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

Paddle the Patapsco River at your own pace in a single or tandem kayak

Cruise Chesapeake Bay waterways with fall views and complimentary warm apple cider

Bring your own food and drinks for a relaxed private cruise with music and river views

Fish the Potomac after dark with a captain-led private charter

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

Build your confidence above the water with step-by-step coaching

Trade city bustle for a relaxed evening under sail

Rent two boats at once and receive a 10% discount

Share time on the water with friends or family

Sail the Miles River with room to relax aboard Epiphany

Pair sunset views with your own music and drinks

Relax on the water with spacious lounges, onboard entertainment, and room to unwind

Trade the city bustle for a quiet cruise along Baltimore's waterfront

Paddle Deale’s quiet creeks and bays at your own pace

Sail the Anacostia and Potomac with an onboard bar and landmark views

Fish year-round from a heated pilot house

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

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

Cruise in classic comfort with personalized service and scenic water views

Cruise quietly with your own food, drinks, and music

Share a Bentley pontoon outing with friends or family