We are a non-profit training center dedicated to raising the level of sailors and sailing in the United States.

It can be difficult to explain Oakcliff to sailors familiar with the typical classifications of sailing institutions.  We are not a yacht club with restaurants and pools; we are not a junior sailing program; we are not a community learn-to-sail program; we are not an Olympic training center – those already exist.

In part, we are a match racing training center.  In part, we are a high-level racing school.  The founders of Oakcliff decided to create a center dedicated to training sailors, boat workers, owners and teams, unlike any other on the planet.  Here you can become a better sailor and learn to run a business in the maritime industry.

Our signature offering, the Acorn and Sapling programs, are raising the next generation of professional racers.  We are filling a gap in the growth path of sailors: before Oakcliff, there was no clear route from dinghy sailing and college sailing to high-level keelboat racing.  We train young, promising sailors in every aspect of the game, from seeking sponsorship to offshore navigation.  Only at Oakcliff can those sailors be taught the skills they need — elsewhere you’re just expected to pick them up, over time.

We sail keelboats. We fleet race. We train teams.  We use match racing because there is no better way to raise your game than a one-on-one fight to the finish. We coach. We train boat captains and boat owners. We match boat owners to boat captains. We coach current business owners. We train future business owners. We plant Acorns, nurture Saplings, and someday they will be the mighty oaks of the sailing world.