Come sailing with Oakcliff’s professional big boat sailors to bring training and knowledge back to your home club

The Junior Sailing Association of Long Island Sound has partnered with Oakcliff Sailing, Oyster Bay NY, to deliver a high-impact spring training “combine” weekend for coaches and experienced junior sailors who want leadership roles and who are ready to elevate their big boat knowledge.

This is not a learn-to-sail clinic. It’s a focused, hands-on program designed to prepare you to coach big boat programs, lead learn-to-race teams, and introduce juniors to inshore and offshore sailing the right way.

Who The Level Up Is For

• 2026 Junior Big Boat coaches
• Intermediate big boat junior sailors
• Strong dinghy sailors seeking big boat experience
• Program directors, volunteers, parent coaches, and experienced staff are also welcome

What You’ll Gain

• Leadership & Coaching
• Tools and knowledge to better coach big boat and learn-to-race programs
• On-board communication strategies
• Team-building techniques
• Leadership skills on and off the water
• Exposure to maritime career pathways

Technical Knowledge

• Big boat safety systems
• Man overboard procedures
• Injury prevention
• Powerboat driving for big boats
• Intro to inboard & outboard engines
• Troubleshooting inboard engines
• Basic composites overview
• Rigging fundamentals
• Basic sail repair

Performance Skills

• Big boat sail handling (tailing, grinding, movement mechanics)
• Practice racing aboard Farr 40s
• Boat-specific fitness training

Take your Junior Big Boat program to the next level. Oakcliff can’t teach everything in a weekend — but they will give you the foundation, perspective, and confidence to level up your sailing and coaching impact before the summer season begins.

View more information and request an application on the Oakcliff website