Guide to the Top Annapolis Water Activities

If you ask us, there's nothing like the relaxation that comes from being on the water. There's something about being away from your on-land obligations that really allows you to take a load off and slip into a happier state of mind. We started our business to make that feeling more accessible, and put this list together to make it even easier for you to soak in everything that the magnificent waters surrounding downtown Annapolis have to offer. Enjoy!

1. Paddle with Capital SUP

Capital SUP provides an accessible and affordable way to explore downtown Annapolis waterways. One location operates at Nautilus Point upstream from Bay Escape, where visitors can rent kayaks or paddle boards for views of boats and waterfront properties. Their Quiet Waters Park location, a five-minute drive away, offers a more secluded South River adventure with wildlife spotting opportunities. Capital SUP organizes multiple events including on-water concerts and sunrise paddle tours.

655 Americana Dr | 600 Quiet Waters Park Rd. | Open Mon – Fri: 10a-8p | Sat & Sun: 8a-6p

2. Take a Sailing Cruise with Schooner Woodwind

Schooner Woodwind offers real sailing experiences aboard two beautiful 74-foot wooden schooners: Woodwind and Woodwind II. The knowledgeable crew encourages guest participation in raising sails and steering, though relaxing is equally welcome. Both private and public sailing cruises are available, including specialty events and multi-day voyages. The company operates between April 15th and October 29th, with tickets available for purchase up to six days in advance.

80 Compromise St. | Hours vary by month, check website.

3. Parasail with Z Flight Watersports

Z Flight Watersports offers parasailing for a unique perspective of the city, thrilling yet safe. Led by a USCG licensed Master Captain with over 30 years of boating experience and more than 10,000 flights, clients receive expert guidance. The company provides competitive rates and private boat charters for up to 12 people. Views of the beautiful Chesapeake Bay are unmatched from this vantage point. Operating season runs May 15th to October 15th.

300 Second St. | Open seven days a week (with exceptions): 9a-6p

4. Learn to Sail at Annapolis Sailing School

Annapolis Sailing School accommodates both children and adults, offering skill development and official certification opportunities. Beyond sailing, powerboat lessons and recreational activities like yoga and racing are available. Private sailboat rentals and regular sunset charters are offered. The school's charming Bembe Beach waterfront location provides an attractive setting.

7001 Bembe Beach Rd. | Hours vary by event type, check booking page.

5. Let Fish with Weaver take you Charter Fishing

Expert fisherman Tom Weaver guides clients to premier Chesapeake Bay fishing locations for rockfish, bluefish, speckled trout, and more. Fish with Weaver earned recognition in Chesapeake Bay Magazine's Best of the Bay as Best Light Tackle Guide and Best Charter Boat in the Chesapeake Bay. You'll feel like a pro by the end of the day! Trips accommodate two to three people best.

317 Chester Ave. | Open seven days a week by booking only: 6a-7p