Acorn Programs


What does it take to race around the world or in the America’s Cup?
Do you want to be the next CEO of North Sails?

If you are interested in pursuing professional sailing, want to learn what it takes to run a marine business, or just want to experience sailing at the highest level, Oakcliff is the place for you.

Trainees are coached by a team of talented sailors and coaches specially selected by Volvo and America’s Cup sailor and Executive Director Dawn Riley. Athletes are led through both basic and advanced technical projects including match racing clinics, offshore races, inshore IRC racing, and land-based learning modules.  They will also have the opportunity to compete against sailors from across the globe who come to Oakcliff. Famous sailors such as Dave Perry and Sally Barkow, and industry experts like Kimo Worthington from North Sails, and Forrest Williams from Marlow, frequently stop by throughout the summer.





June 30 – July 19, 2020 Cost: $3,780
(Need-based scholarships available)

If sailing under the stars, being out of sight of land, and learning what it takes to get to the finish of a distance race sounds enticing, then this program is for you! An intensive program designed by Dawn Riley based on her experience as a skipper and watch captain in two around-the-world races. Get experience being a Watch Captain, Safety Officer, or shadow being a boat captain!
Sail more than 1,000 nautical miles. Get your World Sailing Safety at Sea Certificate and master advanced navigation to thrive offshore. Industry tours and specialized workshops given by leaders in the field provide one-of-a-kind networking opportunities. This is your first step to preparing for the 2022 Bermuda Race.

Follow this link to sign up for the Acorn Offshore session



(CAncelled) OBR (On-Board-Reporter) Acorn

May 20-25, 2020 – Cost:$700

Spend six days focusing on videography, photography, and journalism and test your new skills as an OBR during the Around Block Island Race.

Take your talent home to share with your club.

The program starts with two classroom days going over photojournalism, videography, droneography, and general storytelling. The participants will then be placed on boats in the Around Block Island Race to practice what they learned. After that, they’ll spend two more classroom days learning how to edit their content. The program ends with a BBQ bash on Memorial Day.
This class caters to any skill level, from the seasoned professional to the amateur with a smartphone.

Follow this link to sign up for the OBR Acorn Session!




July 7 – 19 , 2020 – Cost: $2,957
(Need-based scholarships available)

Oakcliff used Melges 24s to run the first test event for the new Mixed Offshore event in the Olympics. This year we will run it in conjunction with the Offshore Program for those keen to explore shorthanded sailing. The rest of the shorthanded fleet includes: Class 40 (Kiwi 40FC). Open 30 and Ker 11.3. This program is limited to 12 participants.

Follow this link to sign up for the Acorn Offshore session




Olympic class 49er and Fx skiffs, WASXPs & Nacra 17 catamarans

June 16-26, 2020 – Cost: $2,563
(Need-based scholarships available)

Our HP program has options for all levels of sailors. Trainees range from high school sailors wanting to get better before college to sailors with serious Olympic plans. Oakcliff is taking a leadership role in training the US Sailing Teams, but even if the Olympics are not your end game you will benefit from training and learning form the squad. We have six foiling Nacra 17s, two carbon Nacra 20s, nine 49ers, nine 49er FXs, and six foiling WASZPs. Private coaching on the High Performance boats are available upon request.

Follow this link to sign up for the Acorn HP session




Match Racing (July 21 – August 2, 2020) and Fleet Racing (August 4 – August 20, 2020) with Top World Sailing Ranked Coaches & Competitors.

 Cost: Fleet $2,975 – Match $2,275
(Need-based scholarships available)

Oakcliff board President and five-time US Match Racing Champion Dave Perry frequently coaches at Oakcliff alongside a roster of America’s Cup and World Match Racing Tour sailors, making this one of the best opportunities to be coached in match racing in the world. Trainees work as a team in match race drills, to hone their skills which they will put to the test in a grade 3 and 4 match race event.

This session trains sailors to manage a boat crew with on-board coaching and physical fitness training. The program provides a full package for the competitive sailor. Learn tactics, sail theory, crew communication, budgeting, logistics planning and technical skills such as winch repair, sail repair. Travel with the team to Canada and race Oakcliff’s C&C 30.

Follow this link to sign up for the Acorn Inshore session




May 12-17, 2020
Cost: $1,740 (Need-based scholarships available)

Foiling Camp is back and our fleet of WAZPs, Foiling Nacra 17s, and 20s will get you up and flying. Our expert coaches will provide personalized advice on how to take your fitness to the next level. This program is ideal for all sailing instructors!
Want to get ahead? Private foiling and coaching on the HP boats are available upon request.

Follow this link to sign up for the Acorn Foiling session

There is a preliminary fitness test that must be passed in order to be accepted into the program. If you cannot complete the test, you will be unable to sail the boats safely. The test involves completing each of the following within a 1 minute time interval: 25 inverted rows, 15 25 lb dumbbell curls, 15 push-ups, 20 air squats, and 25 crunches. You must also be able to run a 5K in under 30 minutes.

Keep in mind, these are the minimum requirements to be safe. The fitter you are, the better. You will be able to spend longer sessions practicing and learn more quickly. 




Can’t commit to a full program?

Dates: Flexible
Cost: $2,500/week

The Custom Acorn Program will give a few select sailors the chance to compete with the young pros according to their own custom schedule. If you can’t commit to a full Acorn program or want to learn specific skills related to performance racing, let us know when you’re available and your interests and we’ll create a custom program for you.

Contact us directly at for more information.