Custom Coaching and Charters

If you are interested in sailing at Oakcliff, but do not have the time for a full-time training program, consider these options.


Everyone who is a supporter of Oakcliff is welcome to train in all of our regularly scheduled racing:
Wednesday night fleet racing in conjunction with Sagamore Yacht Club on our fleet of Swedish Match 40’s, Shields, and more. 


Oakcliff has a variety of custom charter options available to sailors who want to take their racing program to the next level.

Our fleet: Class 40, Kerr 11.3, C&C 30, Kerr 50, 3x Turbo Charged Farr 40s, 6x Melges 24 and many more!

Want to race Around Block Island but don’t have a boat or a full crew?  Want to campaign a Melges 24 or a Farr 40? We can do either bare boat charters or a race sponsorship deal which integrates our trainees with your team. This support is tax deductible to the fullest extent of the law. Contact us to discuss the details.

We also have opportunities to charter our small boats. We have 5 Waszps available for charter for Waszp ACCs May 22-23, 2021. Request a charter


Oakcliff provides customizable programs for sailing teams to train for their season or a big event. We offer coaching on your boat, but encourage all to visit  our facilities – with our large fleet and specialized classrooms, you receive exactly the coaching you need.

In addition to custom training, Oakcliff offers all sorts of seminar, clinics and clinegattas, taught by some of the world’s best coaches.  Check out our calendar to sign up.

Corporate Team Building

Oakcliff offers custom corporate team building programs, including leadership seminars, communication and risk management classes, and sailing outings.  

We will work with you to design a session that provides appropriate challenge to teach your team communication and leadership, or simply to help them bond into a single unit. 

Corporate Sponsorship

We currently partner with international organizations such as Gill, Harken, Marlow, and others, as well as local businesses including the Long Island Sports Hub and Regatta Ginger Beer. There multiple opportunities to partner with Oakcliff and we are eager to make it happen. Please reach out to Executive Director Dawn Riley to discuss the details.