About

With Annapolis known worldwide as "America's Sailing Capital," setting sail across the Chesapeake Bay is a must-experience on your getaway. For a one-of-a-kind voyage, make a reservation with Schooner Woodwind Sailing Cruises.

What makes this outdoor outfitter unique is its classic, 74-foot wooden schooner. These magnificent boats, the Woodwind and Woodwind II, are a familiar sight in Annapolis, known for their striking design and engaging public sails.

Long before Ken and Ellen Kaye became owners of this prestigious sailing outfitter, they were school teachers in Connecticut. Always fans of sailing, they retired early and brought their dream of owning a sailing vessel to life.

The couple commissioned John Scarano in Connecticut to design the schooner, and in 1993, the USCG-approved Woodwinds made its maiden voyage. She sailed down the Hudson River, up the Delaware Bay, through the C & D Canal, and down the Chesapeake Bay to Annapolis.

As Ken and Ellen's business grew, they needed another ship to meet demands. Enter Woodwinds II, a replica of the original, that joined the fleet in 1998. The design of both schooners combines traditional aesthetics with modern safety standards, ensuring a smooth, safe sailing experience. While impressively seaworthy, the vessel's sparkling chrome, white sails, and stained top deck make it eye-catching.

Aside from these gorgeous vessels and the Kayes' professional and friendly approach, the tours are the highlight. From sunset cruises and special events with food and wine, to private charters and yacht club races, there is a voyage for every interest and budget! Additionally, its proximity to the Colonial Annapolis Historic District makes it easy to combine sightseeing with a meal at top-tier restaurants such as Osteria 177.

For the ultimate wind, sail, and surf adventure, book your spot with this top-rated outfitter.

Schooner Woodwind Sailing Cruises: Fun Facts & Cool Features

One of the most notable features is the opportunity to take the helm. Imagine feeling the power of the wind and water firsthand as you sail the Woodwind. While you'll be under the guidance of the experienced captain, this hands-on activity provides an appreciation for the skill required to sail such a large boat.

Another feature worth mentioning is the limited number of passengers allowed on a cruise. While the vessel is USCG-approved for 48 passengers, the crew discovered that when limited to 30, there's more room, and the guests' experience was more enjoyable. Such attention to passengers' well-being, and not filling the deck to make more money, reflects the company's service-first business model.

No matter which cruise you sign up for, you'll sail past some of Annapolis's iconic landmarks. Picture your crew zipping past the United States Military Academy or the Scenic Severn River. Toss in the osprey, other sailing vessels, and the Annapolis skyline, and you'll leave with lasting memories.

Did you know that this East Coast sailing outfitter has connections to Hollywood? In 2005, the Woodwind II was featured in the movie The Wedding Crashers, starring Owen Wilson, Vince Vaughn, and Christopher Walken. In the film, Christopher Walken sails the Woodwind II, adding a fun layer to the vessel's already impressive resume.

Throughout the year, the cruises host a variety of themed events, from beer and wine tastings to history-focused adventures and lighthouse tours. These themed cruises combine the beauty of sailing with other enjoyable activities, making each trip unique.

A sailing trip with Schooner Woodwind Sailing Cruises offers a blend of relaxation, excitement, and education. The combination of beautiful scenery, sea-worthy vessel, and hands-on sailing opportunities makes this a standout attraction to any Maryland vacation.

Local Tips

Book your tickets online in advance; they sell out quickly.
Arrive 30 minutes before your departure to check in.
Hours change seasonally; check online for current times.
Bring a light jacket or sweater; it can be cooler on the water.
You may bring food, but it must be individually packaged for each person.
Only soft-soled shoes are permitted.

Staging environment