Water Activities in Essex, MD

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

Trade city streets for time on the water

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

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

Cruise or fish aboard a stable 23-foot center console

Take to the water with two boats rented together

Relax and cruise the South River on a spacious pontoon

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

Take the helm for a relaxed cruise along the Annapolis waterfront

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

A relaxed captain-led ride through Chesapeake Bay tributaries to Annapolis

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

See three historic lighthouses from the water

Paddle from Eastport or take a sit-inside kayak to your favorite spot

Cruise Kent Narrows waterways with local narration and panoramic views

Take to the water in Baltimore

Leave the cruising to your captain and relax on the water

Learn the essentials of paddleboarding, with a 1-hour rental included

Explore Baltimore’s waterfront with a destination you choose

Fish Chesapeake Bay aboard the 46-foot Lady Luck

See Baltimore’s skyline and harbor from a guided jet ski