Oakcliff Academies

Oakcliff has been training athletes for 10 years sending graduates onto the Olympics, the All-American Offshore Team, American Magic’s America’s Cup team and 11th Hour Racing in The Ocean Race. Our newly redesigned Sapling programs better suit the serious athlete yet still allow for the exposure across disciplines that makes Oakcliff so successful.

This is an intensive program for every curious sailor out there.  We would argue that we are the only place in the world where a 16 year old can steer a boat down an ocean wave one week, foil on a Nacra 17 the next, get a high school education in between and graduate to run a small business or race in the America’s Cup.

This refreshed program allows for serious athletes to custom design their summer experience. Choose your summer long path and become a full fledged Sapling.


Offshore Academy 

Block Island & Annapolis to Newport Intensive I (May 19-June 16, 2021) – Cost: $3,400

Shorthanded Intensive II (June 16-June 28, 2021) – Cost: $1,578

Marblehead to Halifax Intensive III (June 28 – July 30, 2021) – Cost: $3,035 (I,II, and III- $7,500)

The Offshore Academy is built around 4 major events and over 1800 NM of sailing; the Around Block Island, Annapolis to Newport, Marblehead to Halifax and the Melges double-handed event, along with 2 deliveries. Trainees will gain experience in roles such as Watch Captain, Boat Captain, Navigator, Safety Officer and Provisioner. This program will be sailed on Oakcliff’s Turbo Farr 40’s supplemented by the Farr11S, C&C30, and Ker 50.

Click here to sign up.


Maxi Academy

June 28 – August 18, 2021 – Cost: $7,328

New in 2021, The Maxi Academy will take place in the Great Lakes on OC86, Oakcliff’s newly acquired Reichel/Pugh 86 (formerly Windquest). This epic program is a 54-day long program encompassing three major events: the Chicago Mac, Port Huron Mac, and either the Trans Superior race or a trip out the St. Lawrence Seaway. Athletes in this program will be fully involved in the prep, learning how to handle the massive equipment associated with this boat. Coaching will be provided by some top pros along with one of the best superyacht captains and Australian native David Blanchfield, Wisconsin-grown Shore Manager Alexander “Fly” Lulewicz and Executive Director Dawn Riley.  

Click here to sign up. 


High Performance Academy

High Performance Intensive (June 9-16, 2021) – Cost:$1,225

Foiling Intensive (August 18-25, 2021) –  Cost: $1,225

(Need-based scholarships available)

Adapted for all small boat sailors and sailors wanting to get into skiffs or foiling cats, the High-Performance Academy takes part over two individual weeks of group training. Trainees will get professional coaching on 49ers, Nacra 17s and Waszps. Between these weeks we are offering custom training throughout most of the summer to support the needs of different levels of sailors. We have six foiling Nacra 17s, two carbon Nacra 20s, nine 49ers, nine 49er FXs, and six foiling WASZPs. Whether you have a coach and want the support of the Oakcliff facility and boats or you are an entire team looking for group training we have the capacity to put it together.

Foiling Intensive

We’ve chosen the hottest time of the year to sail the fastest little boats. Our fleet of WASZPs, 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 and those looking to take their dinghy sailing to a new level! 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. 

Click here to sign up.



Match Racing Academy in partnership with The World Match Racing Tour

August 4-16, 2021 – Cost: $2,100
(Need-based scholarships available)

The World Match Racing Tour is coming to Oakcliff! Our Match Racing Season will see 14 graded match races and 6 clinics throughout the season, but the Match Race Academy is a two week World Match Racing Tour Endorsed Session that is sure to teach match racers at every level something new. Oakcliff will see an influx of international sailors flocking to Oyster Bay mid-August to compete in the Oakcliff International and Thompson Cup as part of the US Grandslam Series that earns the winner an invite to the 2022 Congressional Cup. While there are many opportunities to match race each summer at Oakcliff, this is your opportunity for a program focused on head to head competition. Rotate through all positions on the boat, train as an umpire, and be coached by the best in the world.

Click here to sign up.

Sapling Summer 2021

Cost: $950/week (Scholarships available)

Unlike previous summers, in 2021 we are allowing interested trainees to create their own full-summer sapling experience by combining intensives from each of the new Oakcliff Academies. By combining an academy or intensive from each of our training blocks, a potential Sapling can fill an entire summer with training and learning experiences at Oakcliff. This means they could dabble in a number of disciplines – say, High Performance and Match Racing – or choose to spend the whole summer diving into offshore sailing.

Follow this link to apply. To qualify as a Sapling, you must choose an Academy intensive from each training block. If you don’t see exactly what you want, do your best to fill out the application. Programming choices can be finalized with your coach.