Things to Do in Annapolis

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.

Emily and Philip Vendemmia look after their students by wrangling a massive schedule of more than 72 classes per week spread over three locations. Bolstered by a strong team of certified Bikram yoga instructors, the duo guides students through Bikram’s 90-minute routine, consisting of 26 postures and two breathing exercises. Instructors crank each studio’s practice space to a hot and humid 105 degrees to help pupils’ muscles safely sink into deep, healing stretches and purge harmful toxins from the body. Each of the standing and seated poses is designed to work every muscle, ligament, and joint while sending freshly oxygenated vampire food to the organs to help support health and fitness.

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.

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.

When Pete and Kate Vonderheide moved from Hawaii to Annapolis to live closer to their family, they thought they'd have to give up a career of ocean kayaking to resume responsible office jobs. Soon they recognized the historic city harbor's lack of kayak tours and knew they couldn't stay inside forever. Their shared passion for history spurred them to research and interview the locals until they'd compiled enough historic material to start leading tours. Today, their tours can teach something new even to locals.

The Vonderheides continue to assemble a team of outdoor guides certified in CPR and first aid who all bear a well-researched knowledge of area wildlife and history. These experts lead two-hour scenic tours through the historic harbor. Starting each excursion with a brief paddling lesson, they put first-timers at ease with basic instruction and an amiable demeanor, unlike guides who rely only on their convincing Captain Ahab impressions. Excursions begin at the Spa Creek headwaters in Truxtun Park and lead participants into open-harbor waters to drift in full view of the state capitol building, the US Naval Academy, and historic Eastport. Trips peak at the City Dock, where participants receive a break to take photos and rest. On the return trip, guides field open-ended questions about city history such as presidential visits, the crabbing and oystering trade, and whether George Washington had to swim using floaties.

The fourth annual Annapolis Arts, Crafts, and Wine Festival will draw a wide array of artists and craftsmen to the Navy-Marine Corps Memorial Stadium, where they'll exhibit their oeuvres to curious onlookers. Visitors examine booths full of paintings, photos, and jewelry and watch as craftsmen manipulate metal, clay, leather, or preconceived notions of reality.

When not soaking up arts and crafts, festival-goers can check out the live jazz playing all afternoon, or indulge in the food and wine tastings. Specialty food exhibitors offer samples of flavored olive oils and vinegars, dips, pumpkin rolls, and more. Children can enjoy the Kids' Art area, with musical and theatrical performances, face painting, and storytelling.