Oakcliff Acorns

Our newly redesigned Acorn programs better suit the serious athlete yet still cater to the needs of novice sailors. Our trainees include campaigning olympians all the way down to high school sailors who just want a summer of training to come back strong in the fall. These programs are open to all abilities and ages over 15 years old. Out trainees are typically a combination of younger sailors and adults: It’s never too late to try something new or refresh your skills!

Our programs offer flexibility, allowing you to pursue your own projects and interests while at Oakcliff. In addition to the core curriculum, we also encourage and budget time for trainees to pursue projects in the world of sailing. In the Acorn program, some days are all sailing; others are focused on shop projects, classroom activities or physical fitness; many are a combination of the two.

Trainees in the Acorn programs live at the Oakcliff Bunkhouse for the duration of the program (if not offshore). The Oakcliff facilities include gender-separated bunk rooms with room for up to eight trainees each, showers, communal bathrooms and a fully equipped kitchen and living room space. Take a virtual tour.


Offshore Acorns 

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 Acorn program 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 Acorns

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

Chicago Mackinac Intensive (July 1 – 19, 2021) – Cost: $3,496

Port Huron Mackinac Intensive (July 19 – August 2, 2021) – Cost: $3,496

St. Lawrence Seaway Intensive (August 2 – 13, 2021) – Cost: $2,400

New in 2021, The Maxi Acorn program 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 Acorns

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 Acorn program 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 Acorns 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 Acorn program 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 Acorn programs. 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 Acorn program 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.

Program Electives

While at Oakcliff, consider focusing on one of our electives! We offer three focus areas for trainees: On board reporting (OBR), race management, and classic boats

Interested in media  and storytelling alongside sailing? We can help you turn that interest into a career or hobby as an OBR. Want to know the ins and outs of running a regatta? Learn race management from our seasoned professionals. Interested in classic yachts? We have a number of classic boats at Oakcliff on which to learn the basics of classics sailing and maintenance.  

We’ll make it easy for you to bring these skills back to your home club or team. Once you’ve applied to our programs, let us know you are interested in one of our electives and we’ll make sure to include it in your education. No idea what you want to do yet? Feel free to stick to the general “liberal arts” sailing education in our programs.

Email Ethan for more information.