Find Your Sealegs in Annapolis, Maryland

Located in Anne Arundel County, with its 533 miles of shoreline—composed of rivers, inlets, creeks, streams and coves, and boasting Chesapeake Bay as its playground, Annapolis offers a bounty of aquatic activities for groups. From sailing, yacht charters and cruises to kayaking, canoeing and paddleboarding, there is no shortage of water-based adventures for groups in “the sailing capital of the United States.” Here are a few to try. 

Set Sail on a Schooner

For over 25 years, Schooner Woodwind Annapolis Sailing Cruises (featured in the movie The Wedding Crashers) has been providing sailing excursions, cruises and racing events on and around Chesapeake Bay. 

Planners can choose from four different team-building activities: “Team Building Fun,” ideal for groups of seven to 35 to learn the basics of sailing together; “Team Challenge,” an interactive experience for groups of seven to 25, designed to increase awareness of team processes and encourage teamwork; “The Ultimate,” which involves a professionally led sailing session, followed by a race between two groups divided between two schooners; and “Crew Match Race,” a team-bonding experience for groups of 14-24 in which attendees join professional crews and captains aboard the two 74-foot schooners—Woodwind and Woodwind 2—in a competitive match race. 

The company also provides customized cruise and tour packages for meetings on the water. Groups up to 48 get exclusive use of each schooner and both boats can be rented together to accommodate more people. Catering, wine and local craft beers are available aboard the boats. 

Take a Tour on a Paddleboard

Planners who want to encourage attendee wellness in between meeting sessions can arrange a group tour with Capital SUP (stand-up paddleboarding). Private tours for more than 40 attendees can be arranged with a professional, certified paddle instructor. Stand-up paddleboards, pedalboards and kayaks are available–beginners welcome. Planners and attendees receive a lesson along with a history tour, an introductory fitness session and a team-building activity. 

Play Captain on an Electric Boat

For small groups who prefer a slower pace, planners and attendees can take turns at the wheel of a battery-operated, eco-friendly Duffy boat from Annapolis Electric Boat Rentals for a unique breakout session, group lunch, or a relaxing team-bonding experience on Annapolis’ beautiful waterways. The boats can be rented for one to five hours and planners can order food and beverages from local restaurants or caterers to bring onboard. Each boat holds up to 10 people; multiple boats can be rented to accommodate larger groups. 

More: Three Reasons to Take your Meeting Outdoors This Summer

Cruise Through Your Meeting on a Powerboat

Island Chill Yacht Charters provides floating venues for meetings, incentive groups, corporate retreats and team building experiences aboard their two vessels: a 34-foot powerboat, Irie Vibes, and a 43-foot sailboat, Therapy. The all-inclusive experiences are customized according to groups’ needs. Team-building events are designed to build communication skills, foster creativity, identify team assets and barriers, and boost team performance while maintaining a spirit of fun and celebration. The Captain, a former research scientist at the National Institute of Mental Health and a practicing psychotherapist, has EAP (employee resolution program) experience and offers conflict resolution training and psychotherapy for meetings and retreats aboard his vessels.