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2014 is a time for celebration at Offshore Sailing School. We (Steve and Doris Colgate) cannot believe how time has flown!!! Just look at us above (Doris on right, Steve, third from right) enjoying a sing-along to lyrics created by crew members while cruising with grads in Tonga – a fair number of years ago . Oh what fun then, oh what fun we are all still having today!


If you completed an Offshore Sailing School sailing certification course, took a sailing lesson, participated in an Offshore Sailing School team building or leadership event, or any other Offshore Sailing School sailing activity in the past 50 years . . . You are eligible to WIN one of these fabulous prizes! 

If you haven't yet joined the Offshore Sailing School roster of happy alumni, there's plenty of time to get involved and join in our 50th Anniversary FUN! See the rules here. 

What you can win:

  • GRAND PRIZE: A priceless private dinner with Steve and Doris Colgate at the New York Yacht Club, plus accommodations at the Club that night and a $500 American Express gift card to use towards travel expenses or incidentals — for two very lucky sailing enthusiasts!  Learn more . . .The New York Yacht Club Model Room

    Photo above: The New York Yacht Club Model Room

  • FIRST PRIZE: A 6-day/5-night Live Aboard Cruising Adventure departing from Fort Myers Beach, Florida on an Offshore Sailing School Jeanneau 439, with an Offshore Sailing School instructor and personal chef, plus two nights' accommodations in two rooms at the fun-filled Pink Shell Beach Resort & Marina —for up to four happy sailors who want to learn more and be pampered! 
  • SECOND PRIZE: A 7-day/6-night sailing vacation at the beautiful South Seas Island Resort on Captiva Island, Florida with daily use of a Colgate 26 sailboat plus dinner for two one evening at the resort's Harbourside GrilI — for two adventurers ready to enjoy the great Southwest Florida outdoors! 
  • THIRD PRIZE: A $500 gift certificate from Gill NA, a worldwide apparel and accessories brand serving the marine industry with over three decades of experience and some of the best sailing gear you'll find for comfort and protection while out on the water!

How to enter:

Fill out the Official Entry Form and include it with your entry. Let your sailing experience with Offshore Sailing School inspire you.
Be creative. Send us . . . 

  • An essay with photos or drawings
  • A  book or poem
  • A video or photo album
  • A special art photo
  • Or any other written or art form . . .

That depicts the sailing lifestyle you have enjoyed since taking a course or participating in a sailing activity with Offshore Sailing School.

If/when you qualify, send us your entry about your sailing experience and lifestyle. . .

It can be as short as you wish, but needs to reflect your love of sailing and what it meant to get involved with Offshore Sailing School. Please make sure you include photos or a video as specified below and on the entry form, to illustrate your story if that is your chosen medium. Please provide an explanation with your entry on the Official Entry Form. 

Cruising World Magazine to Choose the Winner!

Entries must be received by midnight, September 1, 2014

Cruising World magazine will choose the winners. Winners will be notified by September 30 and winning entries will be announced at the U.S. Sailboat Show in Annapolis, MD in October 2014.   

If you have not yet taken an Offshore Sailing School course or lesson, or participated in an Offshore Sailing School team building, leadership or other activity – there's plenty of time to become an Offshore Sailing alum. Call 888-454-7015 and talk to one of our professional sailing advisors and they will be happy to help you qualify for the contest.

Please see the rules here. Entries must be original, produced for this contest and not previously published elsewhere or entered in any other contest. All photos (and drawings if emailing them) should be of high quality (300 dpi or higher and 1800 x 1200 pixels or larger) and in jpeg format. Videos should be no longer than 120 seconds in .mpg or .wmv format or provide URL link to your online video). Essays, poetry and other written forms should be in Microsoft word format. Send your entry via email or snail mail to:

Email: Doris@OffshoreSailing.com

Or mail to:
Doris Colgate
Offshore Sailing School
Attn: 50th Anniversary Contest
16731 McGregor Boulevard, Suite 110
Fort Myers, Florida 33908