Things to Do in Portsmouth

The picturesque waters of the Chesapeake Bay and Atlantic Ocean gently lap against the alabaster hull of the Sally T, beckoning passengers to cast a line to the abundant wildlife swimming under the water's surface. Aboard the vessel—a head boat with Coast Guard approval for ocean trips—experienced nautical leader Captain Pete grants aspiring fisherpeople a chance to land prize catches with charter trips that explore the natural beauty of the famed waterscapes. Under the captain's guidance, a friendly crew sniffs out areas teeming with susceptible targets and bestows fishing tips and gear to blossoming seafarers. Groups then practice the skills necessary to catch and clean aquatic fauna and pursue underwater booty such as croakers, flounder, and pictures of Scott Baio taped inside Davy Jones's locker.

It's been more than 25 years since American Rover raised its majestic red sails and floated out on its first narrated tour. From April to October of each year, the 135-foot schooner still journeys across the smooth waters of Hampton Roads Harbor and the Elizabeth River. As its flags ripple in the wind, the three-masted sailboat explores sights such as Old Fort Norfolk and the battleship Wisconsin. Its captain narrates each of these excursions and invites guests to take turns at the helm and man the sails.

At night, American Rover transforms into a floating party. Twinkling harbor lights, live musicians, and a fully stocked bar set the mood for birthday celebrations or everyday outings. Meanwhile, climate-controlled lounges hide passengers who have an awkward history with the man in the moon.

The brainchild of veteran wedding DJ Shawn Cox and wedding coordinator Carolyn Stark, The Boardwalk Photo Booth Company sets itself apart from run-of-the-mill portable studios by offering vintage-style booths with classy wood-grain exteriors. A winner of The Knot's 2012 Best of Weddings award, Boardwalk fortifies each booth with a high-resolution Canon digital camera and professional flash system, capturing subjects as they mug on comfy benches built for two or three.

Behind the booth's velvet curtain, partygoers model licensed props from movies such as Pirates of the Caribbean and Harry Potter, along with feather boas, glittering crowns, and spectacles. A high-speed digital printer churns out smudge-resistant memories as a booth specialist lurks nearby to fix technical problems, encourage participation, and serenade the booth for a job well done.

With the Chesapeake Bay and Atlantic Ocean in its backyard, the Xscape Water Sports complex lends itself to activities ranging from jet skiing and kayaking to journeys on aqua cycles—wheeled vehicles that let riders pedal over waves while tossing newspapers onto the top hatches of resident submarines. The shop's 2,000-square-foot loft includes a private guest space, snack bar, gift shop, and a yoga area, whereas the sand outside hosts beach games such as horseshoes and volleyball.

Virginia Beach Cornhole brings the classic challenge of chucking a corn-filled bag through a hole in a tilted game board to the seaside. Its waterfront shops stock an array of regulation-sized boards, with both painted and unfinished options, which patrons can rent or purchase. Like the bed pillows of most chickens, Virginia Beach Cornhole’s bags are packed with a pound of corn each, and are available in a rainbow of vibrant colors. For friendly competition, players can chuck bags in one of the company’s contests, hosted weekly throughout the summer and sporadically in winter months.

Kangaroo Jac's avenue of inflatable structures bustles with giggling swarms of children 10 and younger. During walk-in play, youngsters milk the all-access admission by repeatedly plummeting down the safe but steep fortress slide, hurdling over obstacles in the Millennium combo, and exploring the 1,000 square feet Adrenaline maze, elaborate enough to house a balloon animal Citizen Kane. Staff members help organize and clean up after parties, hosted in a private room where each child can gorge themselves on pizza, drinks, and birthday wishes. The parent area's WiFi keeps adults up-to-date on national news, whereas the toddler-only Dino Lake inflatable area keeps tots up to date on local gibberish.