Sapling Program

A six month, immersive apprenticeship-type programs for experienced sailors looking to get a hand up in the sailing industry. Spend a whole summer or winter at Oakcliff, learning all there is to know about racing, boat maintenance, organization and more from the experts at Oakcliff.

Winter Sapling: Jan 21-April 26, 2020 (arrival/departure flexible) Cost: $200 a week plus food

Have a gap year, or time off in the winter? Oakcliff sailing does not stop when the snow flies. Join the team in the boat shop learning absolutely everything that it takes to keep our fleets ready to race. Be first in line for winter racing when available, workout with the team, and even get a head start for a full sapling session in the summer.  

Click here to apply for the 2021 Sapling Program


Sapling 2021 Session May 1-Sept 5, 2021 
Cost: $950/week (Scholarships available) arrival/departure dates flexible

A summer-long dive intro pro sailing through a structured apprenticeship at Oakcliff’s America’s Cup style campus. Gain leadership experience as the boat captain or first mate on one of our 40’ keelboats. Master a wide set of technical skills including marine electronics, rigging, composites, boat building, sailmaking, marine engines, and campaign management. Explore multiple career opportunities with an insider’s perspective from Oakcliff’s coaches and partners.

Through our network, trainees develop relationships that can transition into a career in sailing.

Follow this link to sign up for the Sapling Apprenticeship Program