Top Water Activities in Annapolis

Top Water Activities in Annapolis

Anne Arundel County has 520 miles of shoreline and lies along the coast of the Chesapeake Bay, the largest estuary in the United States. It’s no wonder locals like to spend the summer out on the water, fishing, crabbing and boating. Go ahead and join in on the fun; here are our top water activities in Annapolis.


Capital SUP is nestled in the corner of Spa Creek, with access to waterways including the Severn River and Chesapeake Bay. They offer lessons for beginners; paddleboard yoga; guided tours passing by the Carroll house, Maryland State House and the United States Naval Academy; and Big SUP tours on the “Party Barge,” a 20 foot inflatable stand up paddleboard for 4-8 people. Want to explore the Annapolis waterways at night? Try the LED Night Tour!


Kayak Annapolis offers hourly Kayak rentals, team building experiences like sunset cruises and water scavenger hunts, and kayak tours that will take you through Spa Creek, toward historic Eastport, under the drawbridge and onward to the United States Naval Academy, then to downtown Annapolis’ world famous City Dock, with a view of beautiful historic sites along the whole tour.


East of Maui Surf Shop in Annapolis offers windsurfing, kayak and SUP rentals, as well as paddleboard instruction, windsurfing lessons and an on-site kiteboarding instructor. They partner with Ultimate Watersports, who offers lessons and rentals at Gunpowder Falls State Park in the Baltimore area.

Boat Tours

Schooner Woodwind offers plenty of events, like sunset cruises, brunch cruises and wine tasting cruises, but we personally like the Boat & Breakfast. The evening begins with a two hour sunset cruise, the boat docks so you can grab dinner in Annapolis, then you return to the boat for the evening, followed by a continental breakfast on the water in the morning.


2016 is supposed to be a great year for crabbing, with one of the highest counts in the Chesapeake Bay in the past two decades. Local favorite crabbing spots include the Severn River, Spa Creek and Downs Park. Don’t have the equipment to go yourself? Check out Down Time Sportfishing Charters, whose Crabbing Charters will provide all bait and equipment, help you lay out a traditional Chesapeake Trot Line, and let you keep your catch limit of the day!