Oakcliff accepts trainees with a wide variety of skill levels at a wide range of ages, from absolute beginner sailor to seasoned racer. What we look for is a drive to succeed. If you’re wondering if Oakcliff is right for you, don’t ask yourself, “Am I good enough?” Ask yourself, “Do I want it badly enough?” Trainees who are self-driven, organized, and motivated thrive in Oakcliff’s flexible training environment.
Our program schedules a mix of sailing, boat work, and physical training. We encourage trainees to get interested and show initiatives in their own projects. Have you discovered an interest in sailmaking? Or want to learn all there is to know about managing a sailing team or becoming a boat captain? We will make room in the program schedule so you can pursue your passions.
If you’re having trouble viewing this email, you can see it online. Big Boats Young People! Applications Open! October 30, 2026 TEST Applications for next summer’s training programs are open! World Match Race Tour Academy Midwest Maxi Offshore East Coast Offshore to prep
Day 1 No racing due to severe weather Day 2 Full 7 flights of races Peter Wickwire won the David Storrs Qualifier for the U.S. Match Racing Championship hosted by Oakcliff Sailing in Oyster Bay, New York. The team from Novia Scotia, Canada went
The Harbor Master closed the harbor as the remnants of Tropical Storm Ophelia unexpectedly deteriorated, and racing for day two of the Oakcliff Triple Crown has been canceled. The ILCA 6 and ILCA 7s completed enough races on Saturday to have a regatta and a
September 10, 2023 – World number 1 ranked match racer, Chris Poole and his Riptide Racing bested 55th ranked Gavin Brady and his True Blue racing team at the Oakcliff International claiming the Grand Slam title. The finals between Brady and Poole was first-to-two. Brady
