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St. Michaels, Maryland on the Eastern Shore of Chesapeake Bay

The Inn at Perry Cabin has been sold and, as a result, Offshore Sailing School will not be operating out of this location in 2014. All other locations offer the same courses listed below - in Florida, New Jersey, New York, the British Virgin Islands and our newest location at gorgeous Scrub Island Resort in the British Virgin Islands. Please call 888-454-7015 for more details. 

  • Fast Track to Cruising- a 7-day adventure that takes you from novice to big boat skipper with three sailing certifications
  • Learn to Sail - three action-packed days, weekends or weekdays, or learn over five half-days and enjoy the area
  • Bareboat Cruising Preparation - five days learning to cruise whiile staying ashore at the resort, with time to relax, explore and enjoy other activities
  • Live Aboard Cruising - five days of training while sailing and sleeping aboard as you move from anchorage to anchorage
  • Bareboat Refresher - designed to refresh bareboat cruising skills
  • Two-hour Sailing Lessons - for those visiting the area who just want to try sailing
  • Two-Day Introduction to Sailing - a 6-hour introduction to sailing over two days, leaving time to enjoy other activities
  • Corporate Programs - Half and full-day programs for groups of 10 to 50; build leadership skills and learn what it takes to work together as a team; no previous sailing experience required
  • Private Courses - All regular courses may be taken as a private experience for two or the entire family (maximum 6 people)

Sailing the Chesapeake Button

Or call 888-454-7015 to talk to a friendly sailing advisor