Rent Downtown, Paddle the Chesapeake Bay
Make an Annapolis paddling day of it: grab a kayak or paddleboard from a downtown outfitter, then launch into the calm Chesapeake shallows at a bayfront state park. One stop rents the gear, the other gives you the water. Reserve the board ahead on weekends.
On Spa Creek in downtown Annapolis, this outfitter rents kayaks and paddleboards and runs guided tours and SUP yoga. Rentals start around 25 dollars. It fits first-timers and a weekend group. Open Saturday and Sunday, 8:00 AM to 6:00 PM. Pricing is mid-priced.
On the Chesapeake Bay near the Bay Bridge, this state park has a beach, boat ramps, and calm shallows to launch a kayak or paddleboard. Day-use admission runs about 5 dollars a person on summer weekends. Open 7:00 AM to sunset. Pricing is inexpensive.