Acorn and Sapling Training Programs

Oakcliff is famous for its unique summer training programs.

The Acorn programs offer specialized training in various disciplines including offshore racing, shorthanded sailing, high performance, inshore, and media/onboard reporting. They are designed to be intense but focused elevated training programs.

The Sapling program is a summer long structured apprenticeship that builds all the skills necessary to jump start your success in the sailing industry.  Graduates have working with Vestas 11th Hour Racing and have been training with the New York Yacht Club’s America’s Cup Team American Magic.  There are always new opportunities opening for Oakcliff’s Saplings.

These programs are open to anyone over the age of 15 who is serious about developing their sailing abilities. They are fully immersive meaning that trainees live and train onsite for the duration of the program.


Custom Training


Interested in training for a specific event?  Want to ‘sponsor a boat’ to sail to Bermuda or Halifax? Oakcliff provides multiple customizable programs for teams to train for a season or one big event. We offer coaching on your boat, but encourage all to visit our campus; with our ever growing fleet and unique work environment, we can ensure you receive exactly the coaching you need. Check here for information on sponsoring and chartering.


RacingSeason Long Racing and Clinics

Throughout the season we host and compete in many events including match racing, fleet racing, offshore, and inshore. With the largest variety of sailboats in the country, our regularly scheduled events provide the perfect opportunity for sailors to enjoy themselves while competing in the world’s greatest sport.  Check out our racing page for more information.

Corporate TrainingCorporate Team Building

Sailing is the ultimate team building exercise. It presents unique and interesting challenges that provides the perfect platform for corporate development. Oakcliff offers custom team building programs for groups from 6 to 75, including outings, classes, and more. Please visit our corporate team building page for more detailed information.