2024 Sailing Season is coming! See you April 13, 2024!

Crew Match Race

Experience an ‘America’s Cup-style’ match race while watching from aboard the boats!

Enjoy all the thrills and excitement of a real match race between two of the Chesapeake’s fastest sailboats while relaxing as an on-board spectator! The Crew Match Race pits Woodwind vs. Woodwind II in an America’s Cup-style race, with our professional captains and crew in control.

Top-notch sailing, awesome social experience!  Experience the true performance of our fantastic yachts, and revel in the teamwork and coordination of the crew. Crew Match Races are super competitive, offering guests a rare chance to see a true big-boat match race firsthand! Learn about race tactics, strategy and crew teamwork as the boats sail around the course! This trip is ideal for groups who want to experience the excitement of a match race and observe outstanding teamwork in action, with a less hands-on and intensive sail training program. We can accommodate up to 96 people on both boats; an excellent opportunity for larger groups to experience the thrill of sailing in a real match race, while enjoying a great social atmosphere!

Corporate Cruise on the Schooner Woodwind
Great drinks aboard

Celebrate Your Success!

Woodwind specializes in making your trip truly unforgettable! We have several additions to our team building programs that will make your trip truly unique!


Call Our Staff to Plan Your Crew Match Race! 410-263-1981

Schooner Woodwind