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.

Custom High Performance Training & Charters

We offer specialized, custom training in our high performance boats – including Nacra 17s and 49ers – at the beginning of the summer. You can sign up for custom coaching through our Acorn program application. You can also charter our Nacras and 49ers for regattas, including our Triple Crown Series each fall, or the ODP camps and OCR Regattas in Miami each winter. Find out more about our 49er Charter here and our foiling Nacra 17 charter here.  

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


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

Our fleet: J/V 66, Class 40, Kerr 11.3, C&C 30, Kerr 50, 4 Turbo Charged Farr 40s, 6 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.


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 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.

Exclusive sailing experience

For individuals and small groups interested in a custom-tailored sailing experience, our professional coaches are here to help you develop advanced skills. Our extensive fleet of boats gives you the option to learn sailing at a high-end level and adapt to any discipline you desire. If you are interested in this private coaching, or if you’re not sure what kind of experience best suits you, contact us to discuss the details.
Please note: there is a price minimum of $3,000.