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

Our Qualifications

Check out the Comments of previous charters and new or advancing sailors

Sailing 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.