Schooner Woodwind Sailing Cruises
Sail Away on a 74-foot, classic-styled wooden schooner. Located in Annapolis, noted as “America’s Sailing Capital”, in the heart of the Chesapeake Bay, Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay. As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging and enthusiastic. Sail away with us on either of our twin schooners, Woodwind or Woodwind II.
We offer public cruises up to four times daily, depending on the season.
We also offer amazing private events for your family, friends, and co-workers. From interactive team building events where your team sails the boat after fun instruction, or shmooze cruises where you wine and dine them while sailing. Birthdays, reunions, wedding events, & even celebrations of life cruises are also perfect while cruising on the Chesapeake Bay.
Gareth Asher sings on the Schooner Woodwind
Tour of the 64-foot Schooner Wolfhound (filmed 2018)
Tour of the 65-foot FALKEN by 59 North Sailing after their Transatlantic Crossing in February 2024
Schooner Woodwind Unwraps for the Season
Sail the Woodwind and Woodwind II in Annapolis, MD
Sailing Team Building Program aboard the Woodwinds
Wednesday Night Racing aboard the Schooners: Woodwind and Woodwind II
The Virtual Great Chesapeake Bay Schooner Race
Wednesday Night Races on a heavy air night
She's the Woodwind
Woodwind II in travel lift
Michael Tolcher aboard Schooner Woodwind
Ernie Halter Aboard Schooner Woodwind Performing "Lighthouse"
Natalia Zukerman with Jay Nash aboard the Schooner Woodwind Performing "Gas Station Roses"
Jay Nash & Natalia Zukerman aboard the Schooner Woodwind Performing "Sweet Talking Liar"
Tony Lucca aboard the Schooner Woodwind Performing "Paint a Picture"
Ernie Halter Aboard Schooner Woodwind Performing "Just friends"
Tony Lucca aboard Schooner Woodwind Performing "Anchored"
Ink + Ash - In the Schooner Woodwind Business Office performing "Say you Will"
Ink + Ash - aboard Schooner Woodwind performing "Singin' Man"
Ink + Ash - aboard Schooner Woodwind performing "Scare Each Other"
Ink + Ash - aboard Schooner Woodwind performing "I Release"