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

For an accessible and affordable way to explore the waterways of downtown Annapolis, look no further than Capital SUP. Lucky for you, one of their locations is your neighbor! Just upstream from Bay Escape is Capital SUP at Nautilus Point, where you can rent a kayak or paddle board and get a better view of some of the impressive boats and waterfront properties that populate the area. Or, take a five minute drive to their location at Quiet Waters Park for a more secluded adventure on the South River that offers plenty of opportunities for spotting wildlife. Capital SUP hosts a plethora of events, including on-water concerts and sunrise paddle tours, so be sure to check out their event page.

655 Americana Dr

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

Image courtesy of Schooner Woodwind

2. Take a Sailing Cruise with Schooner Woodwind

Want the real-deal sailing experience? Book a cruise with Schooner Woodwind and tour the city on one of their beautiful, wooden 74-foot schooners, Woodwind and Woodwind II. The friendly and extremely knowledgeable crew encourage participation and will allow you to help raise the sails and steer the boat, but feel free to simply sit back and relax. They offer both private and public sailing cruises, including speciality events and multi-day voyages and operate between April 15th and October 29th. Keep in mind that tickets will not be available to purchase more than six days prior to the day you’ll set sail. Visit their schedule here.

80 Compromise St
Hours vary based on month, check their website

Z Flight Watersports

3. Parasail with Z Flight Watersports

For a truly unique view of the city that is both thrilling and adventurous, try parasailing with Z Flight Watersports. Helmed by a USCG licensed Master Captain with over 30 years of boating experience and more than 10,000 flights, you know you’ll be in expertly safe hands as you soar over the water. They have great rates and offer private boat charters as well for up to 12 people. You’ve never seen the beautiful Chesapeake Bay like this before! Z Flight Watersports’ operating season runs from May 15th to October 15th.

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

Image courtesy of Annapolis Sailing School

4. Learn to Sail at Annapolis Sailing School

It’s never too late to learn something new, or sharpen the skills you already have. Annapolis sailing school has options for both children and adults, and can even help you complete your official certification! If sailing isn’t your thing, they offer powerboat lessons in addition to a host of recreational activities like yoga and racing. You can even rent a sailboat for your own private cruise if you’d like, or join them for one of their regular sunset charters. Plus, their charming Bembe Beach waterfront location is worth a visit in itself.

7001 Bembe Beach Rd
Hours vary depending on event type, check their booking page

Image courtesy of Fish with Weaver

5. Let Fish with Weaver take you Charter Fishing

There’s nothing like spending a day on the water fishing, especially when you have an expert who knows the waters of the Chesapeake Bay better than anyone. Expert fisherman Tom Weaver will show you the best places to catch the east coast’s premier sport fish including rockfish, bluefish, speckled trout and more! Fish with Weaver has been featured in Chesapeake Bay Magazine’s Best of the Bay as Best Light Tackle Guide and Best Charter Boat in the Chesapeake Bay for their consistently amazing excursions. You’ll feel like a pro by the end of the day! These trips are best enjoyed with two to three people.

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

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