Annapolis has long been known for its connection to the water. For many residents and visitors, easy access to the Chesapeake Bay, Spa Creek and the Severn River is one of the area’s biggest draws. As warmer weather and sunny days return, so does the urge to get outside and spend time on the water.
Whether you’re planning a family outing, a group celebration or a new adventure, Annapolis offers plenty of ways to enjoy the sunshine and scenery.
Pirate Adventures on the Chesapeake
Pirate Adventures on the Chesapeake has become a favorite for families with young children. The interactive experience invites kids to become part of a pirate adventure, search for treasure and fire water cannons to fend off enemies along the way. The boat can also be booked for birthday parties, field trips and camp outings.
During the summer, ships sail every 90 minutes, beginning as early as 9:30 AM, with the final departure at 5 PM. Each cruise lasts about one hour and 15 minutes, and guests are asked to arrive 30 minutes before departure. Advance reservations are strongly encouraged. Pre-sale single tickets are $30 per person, with a group option of $120 for four.
Traditional Cruises
Watermark has served Annapolis and Baltimore for years and remains a go-to option for both locals and visitors. The company offers public cruises, private yacht charters, weddings, private cruises and other experiences.
Popular public cruises include the Annapolis Harbor & U.S. Naval Academy Cruise ($25 per adult, $12 per child), the Spa Creek Cruise ($25 per adult, $12 per child), and the Annapolis Sunset Cruise ($36 per adult, $18 per child). The first two will span 40 minutes, with the sunset cruise lasting 60 minutes.For a longer trip, the Bay Lighthouses Cruise takes guests on a three-hour journey past three historic lighthouses and under the Chesapeake Bay Bridge. Tickets are $61 per adult and $21 per child. Watermark also offers a Day on the Bay to St. Michaels trip, a cruise across the Chesapeake Bay to the Eastern Shore town. The trip includes three hours to explore St. Michaels, one complimentary nonalcoholic beverage on the way there and admission to the Chesapeake Bay Maritime Museum. Tickets are $118 per adult and $45 per child.
Capital SUP
Capital SUP offers an active way to explore Annapolis by water, with stand-up paddleboard and kayak rentals, lessons, tours, fitness classes and special events. Based at Nautilus Point Marina in Eastport, the company gives paddlers access to scenic views of local marinas, wildlife, historic Annapolis and the Chesapeake Bay Bridge. Rentals are available for all experience levels, making it a good option for beginners, families, groups or anyone looking for a quieter way to enjoy the water.
In addition to traditional rentals, Capital SUP hosts a variety of experiences throughout the season, including sunrise paddles, eco tours, yoga and fitness classes, Ladies Night, Yappy Hour paddles and other special events. Rentals start at $25 and typically last one to two hours, with longer rental options also available.
Sailing Cruises
For those looking for a classic Annapolis sailing experience, Schooner Woodwind offers public and private cruises aboard two 74-foot wooden schooners. Departing from the historic Annapolis waterfront, the cruises sail past the U.S. Naval Academy and into the Chesapeake Bay. Guests can help raise the sails, take a turn steering the boat or simply relax and enjoy the view. Public sailing cruises typically last two hours, with sunset sails and special events also available.
The Annapolis Maritime Museum & Park also offers sailing tours aboard the historic skipjack Wilma Lee. Its Heritage Tour focuses on Annapolis’ maritime history and Chesapeake Bay ecology, with guides sharing information about the city’s boatbuilding industry, watermen, oyster harvesting, local wildlife and landmarks such as Carr’s and Elktonia Beach, Eastport and the Naval Academy. The museum also offers sunset cruises, Wednesday Night Races watch parties and specialty cruises during the sailing season, which runs through Oct. 31.
Tiki Boat Cruise
For groups looking for a more festive outing, Sea Suite Cruises offers a private tiki boat cruise in Annapolis. Formerly known as Naptown Tiki Club, the floating tiki boat departs from Nautilus Point Marina and can accommodate up to 16 passengers.
The cruise is bring-your-own-beverage, and guests may also bring their own food and playlist. The trip lasts one hour and 45 minutes and requires a minimum of eight passengers to depart. Tickets are $45 per person. Passengers must be at least 5 years old, and anyone consuming alcohol must be 21 or older.
Dragon Boating
The Annapolis Dragon Boat Club offers a more active way to get on the water. Rather than sitting back for a cruise, participants paddle together in long dragon boats on Spa Creek. Think rowing, but with a larger team and a drummer setting the rhythm at the front of the boat.
Dragon boating has become especially popular among breast cancer survivors because of its physical and social benefits, including building strength and endurance, supporting recovery and creating a strong sense of community.
The club has two dragon boats, each of which can hold 22 team members: a drummer in the front, a steerperson in the back and 20 paddlers seated in two rows. The year-round club practices on Spa Creek and travels throughout the region for races and competitions.
Open practices for all experience levels take place Tuesdays from 5:30 to 7:30 PM. Wellness paddles, designed for those in active treatment or recovery, are held Wednesdays and Saturdays from 8:30 to 10:30 AM. Discovery paddles, which are open to guests, take place on the fourth Saturday of each month from 8:45 to 10:45 AM. Annual membership dues are $200 for paddlers and $75 for nonpaddlers.
With so many ways to enjoy Annapolis from the water this summer, the only question is which adventure to try first.
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