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Chesapeake Bay is home to legendary beautiful waters, diverse flora and fauna, and Paddlefest, an annual paddle-sports event organized by the team at Ultimate Watersports. Held on the Gunpowder River, which flows into the bay, the festival shows off the industry's latest toys, allowing attendees to try out brand-new kayaks and paddleboards on the sparkling fresh water. For the rest of the season, Ultimate Watersports brings its know-how to the shores with kayak tours, paddleboard lessons, and sailing trips that have remained a bay fixture for more than 26 years. Waterfront enthusiasts seek out the company's reliably well-maintained and up-to-date watercraft to do everything from gain a windsurfing certification to practice heckling standup paddleboard comics. Additionally, seasonal kids' camps help youngsters to stay active while gaining an appreciation for watersports and the splendor of the outdoors.:m]]
7200 Graces Quarters Rd.
Affiliates of the American Sailing Association, the instructors at Chesapeake Sailing School strive to keep the Chesapeake's seafaring heritage alive through classes spanning one-day sailing courses to five-day live-aboard cruises. The training fleet ranges from 22-foot boats for basic and intermediate instruction to 38-foot vessels for advanced cruise training. The school's team also assists students obtain their ASA certifications in preparation for careers as Popeye impersonators.
Beyond instruction facilities, Chesapeake Sailing School houses The Tiller Club, which grants members privileges such as unlimited daily use of the school's Tanzer 22 ships. The school’s team also coordinates charter excursions to give vacationers a from-the-water view of the Inner Harbor, St. Michael's the Archangel Church, and the bay's abundant wildlife.
7080 Bembe Beach Rd.
At the Maryland Drafts and Laughs Festival, attendees sample suds from taps dispensing more than 50 craft and imported brews. As festival-goers make their way among breweries such as Port City and Yuengling, they can break for comic relief at one of five standup shows. There, regional comedians culled from Last Comic Standing, Comedy Central, and Sirius XM Radio entertain with adult-brand humor. Visitors can also sit in on presentations and Q&As with brew masters from Flying Dog and Heavy Seas, asking them about their unique brewing process or how many elves it takes to seal a beer can once it's been filled. To sustain the unlimited sampling, food and soda will be available for purchase.
1100 E College Pkwy.
Committing their enterprise to eco-friendly tourism, the women at SegZone Tours guide visitors through the historic streets of Annapolis, along the city waterways of Dover, and around the track at Dover International Speedway—all aboard segways. For groups or private parties, tour leaders can also focus excursions on local gardens, architecture, and wildlife in areas often unreachable by car or paraglider. They also guide themed seasonal tours, such as rides along haunted-house routes or past holiday-light displays. With an eye toward safety, staff members always provide thorough instruction on riding before tours or rentals, though they often give customers license to race or argue over whose segway would look better with flames painted on the side. When not leading guided excursions for customers or school groups, the team organizes corporate team-building events as well as indoor obstacle courses for recreation.
131 Prince George St.
Historic Annapolis at St. John’s College preserves and celebrates the area’s rich social and political history with tours of the colonial city and its landmark homes. The nonprofit group restored the Paca House & Garden, National Historic Landmark, to its colonial-era glory so that visitors could wander the rooms and gardens and travel back in time to an era teeming with revolutionary political ideas and patriotism. A historical museum holds exhibits that illuminate the past, such as a six-foot-by-six-foot model of 18th-century Annapolis and a wormhole to Ben Franklin’s kite shop. At Hogshead at 43 Pinkney Street, living history presentations immerse visitors in the language and thoughts of long-ago citizens. Historic Annapolis also hosts a variety of public events, from historical interpreters presenting on colonial life to summer camps for burgeoning history buffs.
99 Main St.
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