And we’re sailing! Our season started in April.

Fun Cruise Ideas

Team Building Ultimate Race between the two schooners
Team Bonding with a Crew Race on Schooner Woodwind

Sail Away on a 74-foot, classic wooden schooner, Woodwind and Woodwind II for your special private event.

Our schooners are renowned for their sailing qualities while providing a comfortable, roomy deck and cockpit for relaxing or enjoying food & spirits. The best way to experience the Chesapeake Bay is under sail in “America’s Sailing Capital”, Annapolis, Maryland.

Fun packages for Private Cruises can be arranged easily to suit your needs and budget. We can accommodate up to 40 guests on each vessel.

  • Team Building– Sailing requires teamwork, collaboration, trust, communication, and coordination. Learn how these core skills of teamwork create a fun and interactive sailing experience for your entire team.
  • Lighthouse Tours– Sail to as many as three different lighthouses on the Chesapeake Bay and learn about their history, importance, and present-day condition.
  • “Sails” Incentives – A private cruise on the Chesapeake can be a memorable gift to reward your staff for a job well done.
  • Brews in the Breeze – Time to partake of some regional microbrews and appetizers with a fun-filled tasting on board!
  • *Not Currently Available for 2022 (crabs are scarce!)* Sailing to a Crab Feast – The thrill of sailing to a local crab house for a sumptuous seafood feast!
  • Weddings Small, intimate weddings while under sail make for a special event.
  • Brunch Cruises- Enjoy the morning breezes with a gourmet brunch and delicious morning cocktails of Mimosas and Bloody Marys.
  • Sail to St. Micheals on Maryland’s Eastern Shore- Charter the Woodwind for the day and enjoy time on the water and walking around the historic town.

These packages are customized to your group’s needs and availability.

Contact a Schooner Woodwind Sales Agent

Learn more about group sailing and sailing aboard the Schooner Woodwind & Woodwind II

Call 410-263-1981, or fill out an inquiry form by clicking on the button below.

Schooner Woodwind