Sapling Program

The Sapling program is a 3-6 months long, immersive, apprenticeship-type program for experienced sailors looking to get a hand up in the sailing industry, or want to try all different sailing disciplines before deciding their focus. 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: Fall Sep 1 – Dec 17, 2024 & Spring Jan 16 – May 6, 2025 

(Arrival/departure flexible – program charged by the week) 

Cost: $200/week plus food or $3,500 per semester (Scholarships available)

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, get pro workout coaching from the team, and even get a head start for a full sapling session in the summer. Check out the full schedule

Summer Sapling: May 6 – Sept 4, 2025 

(Arrival/departure flexible – program charged by the week) 

Cost: $950/week (Scholarships available)

A summer-long dive intro pro sailing through a structured apprenticeship at Oakcliff’s America’s Cup style campus. Try our all disciplines of sailing throughout the summer, from high performance to offshore to match racing. 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.