Inn at Perry Cabin: Sailing Lessons Chesapeake

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Chesapeake Bay Sailing Lessons

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, Spa & Marina, 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)

Choose a Course Below for a Detailed Description

Fast Track to Cruising® Course

During the first two days you are immersed in our comprehensive Learn to Sail course, which takes you through intermediate sailing knowledge and skills on lively Colgate 26 sailboats. Maximum four people taught per instructor per boat. You may also choose to do your cruising lessons while living aboard. Packages include:

  • Accommodations and room tax at the resort for 7 nights with Bareboat Cruising Preparation course or 3 nights with Live Aboard Cruising course
  • Tuition
  • Textbooks
  • Three certifications
  • Diploma and logbook

The next five days you'll learn on a fabulous Jeanneau 439 and go home with three sailing certifications:

  • Day Sailing
  • Coastal Cruising
  • Bareboat Cruising

Learn to Sail Course                             

Learn on the award-winning Colgate 26 sport boat, designed by our founder Steve Colgate and famed yacht architect Jim Taylor. This is the most comprehensive, best known course to get you thoroughly ready for sailing mid-sized sailboats. Three full days or five half-day schedules are available.

Packages include:

  • Accommodations and room tax at the resort for three or five nights
  • Tuition
  • Textbooks
  • Certification
  • Log book
  • Diploma

Pick your start date:

  • Three full days – Monday through Wednesday or Friday through Sunday
  • Five half days – Monday through Friday (the most relaxing way to learn)

Learn to Cruise

Our five-day Bareboat Cruising Preparation course is the perfect next step if you have taken our Learn to Sail course or have equivalent experience. You start with a morning classroom session, and then learn in half-day sessions. Your on-water schedule normally alternates mornings and afternoons throughout the week with a rewarding test sail without the instructor aboard on your last day. Each evening after you'll return to your beautiful room ashore.

Packages include: 

  • Accommodations and room tax at the resort
  • Your course tuition
  • Textbooks
  • Two cruising certification levels
  • Diploma
  • Logbook
  • For Live Aboard only - all breakfasts, lunches, snacks and three dinners aboard

Weekend Bareboat Refresher Course

This weekend course allows you to refresh your big boat skills while staying at this beautiful resort. You get lots of experience handling our Jeanneau 439, relearning the skills you need for bareboat chartering. Packages  include two nights and room tax at Belmond The Inn at Perry Cabin, and eight hours of instruction on the Chesapeake Bay aboard the Jeanneau 439.

Two-Day Introduction to Sailing

This two-day mini-vacation is a great introduction to sailing. You'll learn in two three-hour sessions - six hours total over two days, allowing free time to explore the area and relax. Packages include your six hours of instruction and two nights with room tax at the resort.

Sailing Lessons

If you just want to get a taste of sailing, try our two-hour sailing lesson on a fun Colgate 26. A two-hour lesson is $150 per person, minimum two people (or $600 if two people desire private sailing instruction for two hours together). Each additional hour is $75 per person.

Corporate Programs

This exclusive program is available at groups up to 50, depending on location. If you are planning a meeting, consider adding a half-day or full-day corporate team building or leadership development program to bring everyone together in an exciting atmosphere to try something new and build confidence among teams during sailing and racing exercises. 

Pricing starts at $299 per person for the half-day session; $399 full day - minimum four participants per boat on two Colgate 26 sailboats with expert coach/instructors. 

Sailing the Chesapeake Button 

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