Fast Track to Cruising Courses for Women Only


If you’re looking for the top women’s sailing classes in Florida, look no further! Fast Track to Cruising® (OSS 101/103/104) sailing for women courses start with two days learning to sail a lively Colgate 26 keelboat (OSS 101) and then six days learning to cruise on a big monohull (OSS 103/104) or catamaran (OSS 103/104/114). You go from “couch to the captain’s chair” in just one week, in Offshore Sailing School’s most popular and comprehensive experiential sailing vacation – the Fast Track to Cruising® course. Even if you have some experience on small boats, or have taken a basic sailing course at a community sailing school  or another commercial sailing school, this Fast Track sailing course is the best way to get your skills and knowledge up to speed. Come alone or bring your mom, sister or a friend for our ladies only sailing courses. Either way you’ll have a blast and enjoy the camaraderie that comes with women learning together. Watch a video recap of four girlfriends enjoying their Fast Track to Live Aboard Cruising course from Scrub Island Resort, Spa & Marina here. They were such competent and confident skippers by the end of the course, they immediately embarked on a bareboat charter from The Moorings, bringing family and friends along. What fantastic memories they made during our sailing lessons for women. Well done Captains!


If you have keelboat sailing experience and can confidently steer and crew in all positions on a mid-sized sailboat of at least 26 feet, you may take the Live Aboard Cruising course (OSS 103/104) without the two-day Learn to Sail portion (OSS 101). However, that assumes you already have US Sailing Basic Keelboat Certification. If you do not have US Sailing Basic Keelboat Certification  you will need to take and pass the Online Learn to Sail Course produced by Offshore Sailing School and Boat US and submit your certificate of completion and a resume for review. If approved, you may then sign up for just the Live Aboard Cruising Course, and take the US Sailing Basic Keelboat test (additional fee of $75) which is a prerequisite before you can take the US Sailing Basic Cruising and Bareboat Cruising tests administered during the Live Aboard Cruising Course. For more information about our women’s sailing courses, feel free to contact us!

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Call 888-454-7015



  • The Learn to Sail and Live Aboard Cruising Courses
  • Three nights accommodations ashore, with room tax and daily resort fee
  • Shared or private cabin aboard the cruising boat during the 6-day cruising course
  • All breakfasts, lunches, snacks, three dinners aboard during the live aboard course
  • Doris Colgate’s book: Sailing – A Woman’s Guide
  • US Sailing books: Basic Keelboat, Basic Cruising, Bareboat Cruising
  • Three US Sailing certifications, tests administered during course: Basic Keelboat, Basic Cruising and Bareboat Cruising and catamaran endorsement if learning on the cat
  • Diploma, Logbook and Certification Stickers for each course
  • Eligibility to join our Colgate Sailing Adventures® flotilla cruises
  • Many Alumni Benefits, such as, complimentary subscription to Cruising World or Sailing World magazines (sent to U.S. mailing address)
  • Discount on your first charter with The Moorings
  • Complimentary first-year membership in US Sailing
  • Discounted memberships in BoatUS


The following dates have been designated Women’s Week Fast Track to Live Aboard Cruising Courses at Scrub Island Resort, Spa & Marina in the British Virgin Islands, and the Pink Shell Beach Resort & Marina on Fort Myers Beach, Florida. Please note locations for each date. Call 888-454-7015 for additional dates as we continue to add more Women’s Week Courses.

Women’s Week dates: 

April 11-18, 2020 (arrive 4/10) – Scrub Island Resort, British Virgin Islands (view the video on this page). ONLY 1 CABIN LEFT!
$7305 single in private room ashore and cabin aboard
$5770 per person double occupancy in room and cabin
$6545 per person double occupancy in room ashore, private cabin aboard

May 16-23, 2020 (arrive 5/15) – Fort Myers Beach, Florida – SOLD OUT. See other available times
$5870 single in private room ashore and cabin aboard
$4805 per person double occupancy in room and cabin
$5395 per person double occupancy in room ashore, private cabin aboard

These women-only sailing courses are taught by expert Offshore Sailing School staff instructors who are US Sailing-certified at the Instructor Bareboat Cruising Certification level or higher. Because Offshore Sailing School’s faculty is made up of more men than women, should a woman-instructor scheduled to teach become unavailable, this course may be taught by one of Offshore Sailing School’s caring, very experienced and patient Offshore Sailing School male instructors.

Every photo on this page was sent to us by women who took an Offshore Sailing School Fast Track to Cruising course. Call to talk to one of our friendly sales associates and learn how our sailing lessons for women can open up a sea of opportunities!
Contact Us Today!

Call 888-454-7015

SAILING – Good for You. Good for the World!™