So, you’re coming to Annapolis. If you’re fortunate to visit when the weather’s warm, you’ll probably want to get out on the water. There are plenty of ways to enjoy it, but maybe you’re ready for something a little different, edgier, unusual. We’ve got just the thing.

In fact, we’ve got more than that. Here are five fun ways to enjoy being on the water during your time in Annapolis. There’s a good chance you’ll discover at least one that you’ve never tried before.  

Boat & breakfastExperience a ‘Boat’ and Breakfast 

You’ve heard about bed and breakfasts, maybe even stayed in a few before. But how about a “Boat and Breakfast” adventure? It’s possible in Annapolis. You’ll climb aboard a beautiful 75-foot sailing yacht that accommodates as many as four couples and prepare for the overnight stay of a lifetime. First on the agenda is a two-hour sunset sail on the Chesapeake Bay. You’ll disembark for dinner at one of Eastport’s top-tier restaurants before heading back to the boat at its designated dockside mooring, where star gazing and a good night’s sleep await. Next morning, you’ll wake to bay breezes and a specially prepared breakfast. 

Try stand-up paddleboarding—at night. 

Perhaps you’ve tried stand-up paddleboarding (SUP), the latest in water sports that originated in Hawaii as an offshoot of surfing. Like it sounds, SUP involves standing on a board and paddling through the water. Now, for the truly adventurous, Annapolis offers nighttime SUP. Here’s how it works. With state-of-the-art LED light systems attached to the bottom of the boards, paddlers hop aboard and follow a trained guide through the waterways of Annapolis. To add to the fun, the tour guide leads the way with a portable waterproof sound system attached to his or her board, so paddlers enjoy a party-like atmosphere with non-stop music throughout tour, highlighted by a paddle down Annapolis Harbor’s Ego Alley

Let the wind be your engine as you wind- or kite surf. 

Do you windsurf or kitesurf? Then bring your board and gear when you come to Annapolis and the Chesapeake Bay. A handful or so of select parks offer great launch points for both wind- and kite surfers. Your friends with kayaks and canoes can also take off from these same spots. So pick a windy day, catch some of that wind with your board, and then head to one the area's many restaurants or pubs afterwards to round out your day.

Take to the Chesapeake Bay as a Pirate.  

All aboard the mock-pirate ship, Sea Gypsy. Once on deck, kids dress up like pirates, troll the waters of the Chesapeake for sunken treasure, battle other ‘pirates’ with water cannons, and engage in other fun and silly sea-worthy activities. Hosted by Annapolis company Pirate Adventures on the Chesapeake, this family immersion experience is made ever more realistic thanks to great costumes for the kids; enthusiastic crew members who make their pint-sized charges shriek and laugh; and phenomenal props including a life-like cannon and, of course, a ship that really looks as though it could belong to a band of pirates. 


Take the water taxi.

For a quick, fun and scenic way to various points in Annapolis, try the Watermark Water Taxi. It travels through the Annapolis Harbor as well as Spa Creek and Back Creek. In addition to designated pick-up times, it also picks up customers upon request (with advanced notice). Get more details here