Why Choose Us?

What makes us special? 

  • Adaptability to your needs

    • we can adapt our charters and instruction courses to fit you!
  • Small Charter or Class Size 

    • To afford plenty of personal attention, our courses are limited to six students maximum.
    • Courses are aboard a large, fully-equipped, clean, comfortable, recent-model sailboat.
    • Charters are limited to a maximum of six people.
  • Location on the Chesapeake Bay

    • Located just minutes a few miles south of Annapolis, we're 45 minutes from Baltimore or Washington, D.C.
    • Water-wise, located just below Annapolis, we have access to the nice scenery of several rivers and the whole big bay!
  • "No Yelling" Women-Only or Teenagers-Only classes

    • Sometimes you can neither learn from or teach to the people you love the most . . .
  • Group Discounts


Feel free to review our qualifications.

Courses are aboard DreamCatcher, a 1995 Center Cockpit Hunter Passage 42.

MainSail Charter’s Instructors are United States Coast Guard Licensed Merchant Mariners with federally recognized boating skills.