Work with Us

Imagine living in paradise for a few weeks to a year while helping to build out the world’s top adventure sailing school. With Sailing Virgins Contra Program, you can see the world, make great new friends and learn to sail, including earning your ASA Sailing Certification, all while enhancing your portfolio.

This is possible with our Contra Program. Essentially we partner with passionate, adventurous people who are experts in a craft that is desirable for us to grow the business.

Skills We’re After

  • Copywriting
  • Videography/photography
  • Social Media Management
  • Any other valuable skill that you think we should look into

The Details

The talent (ie. you) applies for the position by filling in the form below and works with us to scope out a project that adds up to an equivalent monetary value as a sailing course (around $2,500-$3,000). Strong preference is given to projects that have tangible outputs of work and drive business value (videos, blogs, campaigns, rather than simply advice/coaching). Upon completion of the work (or during the execution of the work), the talent receives a free sailing course(s) with us.

Furthermore, after completing an initial contra project, we are happy to kick off deeper engagements including paid gigs and cost-of-living sponsorships on location in the Caribbean. Of course, each specific engagement is done on a case by case basis.

Examples of Past Contra Engagements

Social Media Giveaway – Talent developed and managed a social media giveaway that garnered thousands of new leads and two booked courses in an 8 week period

Videography – Talent shot and produced a suite of high-quality YouTube episodes that garnered tens of thousands of views and thousands of new subscribers

Email Marketing Campaign Setup and Execution – Talent crafted strategy and executed on delivery of email marketing campaign that drove six booked courses

Next Steps

If you’re interested in working with us in exchange for earning your sailing certification, apply below. Be sure to emphasize past relevant work and offer a clear proposal of services you can deliver.




Happy Sailing!