Annapolis Sailing Private Cruises around the Chesapeake Bay aboard the Schooner Woodwind

Milestones on the Bay

Celebrate your next occasion on the Chesapeake aboard a private charter.

Social Sailing Cruises

Annapolis Your Way

Our private charters are the best way to view the stunning sights of our area.

Fun Cruise Ideas

Custom Corporate Outings

Exclusive cruise, exquisite food. Come aboard our private charters.

Corporate Cruise Ideas

Private charters can include your choice of custom catering. Our professional staff can deliver on the details, from planning to pleasing your palate.

Scrumptious Sailing

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Your teams will learn how to sail and race two 74 foot schooners on the bay.

The Ultimate Team Challenge

Corporate Team Building Programs

Private Sailing Cruises

Click Here to Learn About Our Team Building Programs

Private Sailing Cruises

To reach the sales staff and arrange the trip of a lifetime aboard Woodwind, please fill out the form below or call 410-263-1981, or email us.