Oakcliff Sailing

What Oakcliff Sailing does

Oakcliff Sailing is a 501(c)(3) non-profit organization founded in 2010 and headquartered in Oyster Bay, New York, that operates as a youth and adult training center for competitive sailing. The organization serves athletes who have progressed beyond traditional coaching methods and are pursuing professional careers in America's Cup, Olympic, and Ocean Race campaigns, with program tiers segmented by age (Acorn Programs for ages 15+, Sapling Program for adults 18+, and High Performance High School) and discipline (Midwest Acorn, High Performance, Offshore, Match Racing). Oakcliff also offers ancillary revenue-generating services including custom coaching and charters, corporate team-building programs, safety-at-sea seminars, and hosted regattas such as the Oakcliff International and the Wednesday Night Racing Series.

The organization's physical infrastructure forms its core technology platform: an America's Cup-style training campus with a 40-person dormitory, full-service boat shop, and a diverse high-performance fleet that includes Swedish Match 40s, Farr 40s, Shields class boats, Class 40 offshore boats, and historic 12 Metre yachts including Courageous (1974 and 1977 America's Cup winner). Oakcliff campaigns select vessels competitively, including participation in the Atlantic Cup double-handed offshore race and the 12 Metre World Championships.

Oakcliff operates under a non-profit revenue model combining program tuition, tax-deductible donations, need-based and named scholarships (America True, Jacques Rogge Olympic Pathways), corporate team-building fees, regatta hosting fees, and sponsorships from industry partners. Its go-to-market leverages designated status as the official U.S. Sailing National Training Center (since 2013), formal partnerships with NYYC American Magic, World Match Racing Tour, 11th Hour Racing, Dream Yacht Charter, and IYRS, plus multi-channel marketing across social media, email, earned PR, and on-site events. Reported outcome metrics include a 90%+ graduate employment rate in professional sailing.

Name

Oakcliff Sailing

Legal name

Oakcliff Sailing

Website

https://oakcliffsailing.org

Company type

Private

Founded year

2010

Operating status

Operating

Headcount range

11–50 employees

Short description

Oakcliff Sailing is a 501(c)(3) non-profit training center in Oyster Bay, New York, offering youth and adult sailing programs on a high-performance fleet to develop athletes for America's Cup, Olympic, and Ocean Race careers.

Ownership category

akta.pro rank

Product category

Sailing Training Services

NAICS

Marinas (713930), Marinas (71393)

SIC

Services-Membership Sports & Recreation Clubs (7997), Ship & Boat Building & Repairing (3730)

akta.pro primary industry

Sailing Experiences (Lessons, Regattas, Day Sails) (THAJAJAG)

akta.pro secondary industries

Sailing & Water Sports Teams/Clubs (Sailing, Rowing, Surfing) (MPAKABAH), Educational Cruises & Shipboard Learning Programs (THAKAGAM)

Keywords

• Sailing training programs
• Match racing training
• Offshore sailing education
• Professional sailing workforce
• Marine industry development

Headquarters

HQ city

Oyster Bay

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Operations, Infrastructure, Marketing or Sales, Others

Distribution channels3 records

Marketing channels4 records

Core offering

Oakcliff Sailing is a 501(c)(3) non-profit training center that delivers advanced sailing instruction and apprenticeship programs for youth (15+) and adults aspiring to professional sailing careers. Core offerings include the Sapling apprenticeship program for adults, multiple Acorn programs for high school-aged sailors, custom coaching and charters, safety-at-sea seminars, and hosted regattas. The organization also runs corporate team-building events and manages a working fleet of high-performance vessels including Match 40s, Farr 40s, Shields, Class 40, and historic 12 Metre yachts.

Product overview

Oakcliff Sailing is a youth and adult training center located in Oyster Bay, New York, offering sailing programs as its core product. The organization operates a multi-tiered program structure including the Sapling Program (apprenticeship for adults 18+), Acorn Programs (training for ages 15+), and High Performance High School programs. Additional offerings include custom coaching and charters, corporate team building, safety at sea seminars, and regatta hosting (match racing events, Oakcliff International, and the Triple Crown Series). The programs are designed to develop professional sailors for careers in America's Cup, Olympics, and Ocean Race competitions.

Differentiator

Problem solved

Functional benefit

Products and services

• Sapling Program An apprenticeship program for adults (18+) designed to train sailors for professional careers in sailing and the marine industry, offering flexible training schedules that mix sailing, boat work, and physical training.
• Acorn Programs Training programs for individuals aged 15 and older, including Midwest Acorn Program, High Performance Acorn Program, Offshore Acorn Program, and Match Racing Acorns delivered in partnership with the World Match Racing Tour.
• High Performance High School A high-performance training program for high school students who want to advance their sailing skills beyond traditional coaching methods.
• Custom Coaching and Charters Bespoke sailing coaching and charter services tailored to individual or group needs and goals, available for custom sailing experiences.
• Corporate Team Building Team-building programs using sailing activities designed to develop leadership and collaboration skills for corporate groups.
• Oakcliff Safety At Sea Seminars Safety training seminars covering essential safety protocols and procedures for sailing, provided for sailors at various skill levels.
• Oakcliff Regattas Competitive sailing events including match racing regattas, the Oakcliff International, and various graded competitions (Grade 2 through Grade 5 Clinegattas).
• Wednesday Night Series Weekly Wednesday evening racing series presented in partnership with Dream Yacht Charter, offering keelboat racing with onboard coaching.

Quantifiable outcome

• 90%+ employment rate for graduates in professional sailing careers
• +1 more outcomes

Segments2 records

Ideal customer profiles2 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature3 records

Partnerships

Eight partnerships are on record, tiered minor and core.

• Dream Yacht CharterminorGTM or Marketing Partner · 27 April 2016Oakcliff partnered with Dream Yacht Charter to present Wednesday Night Racing Series. Dream Yacht Charter offers over 700 yachts in 43 destinations for bareboat and crewed charters. Sailors who participate in Oakcliff racing receive discounts on charters.
• US SailingcoreStrategic or Co-development Partner · 10 January 2013Oakcliff Sailing named official US Sailing Team Sperry Top-Sider Training Center through partnership with US Sailing. Through the generous support of Oakcliff founders Hunt and Betsy Lawrence, Oakcliff provides training facilities for US Sailing athletes.
• 11th Hour RacingcoreStrategic or Co-development PartnerOfficial Partner of Oakcliff Sailing. 11th Hour Racing is also sponsor of the Atlantic Cup presented by 11th Hour Racing.
• NYYC American MagiccoreStrategic or Co-development PartnerOfficial Partner. New York Yacht Club American Magic is Challenger for the America's Cup. Oakcliff collaborated with American Magic to host training and tryouts with Oakcliff graduates.
• IYRS (International Yacht Restoration School)minorStrategic or Co-development PartnerOfficial Partner of Oakcliff Sailing.
• World Match Racing TourcoreStrategic or Co-development PartnerOfficial Partner. Oakcliff hosts Match Racing Acorns in Partnership with the World Match Racing Tour.
• UPSA (U.S. Professional Sailing Association)minorStrategic or Co-development PartnerOfficial Partner of Oakcliff Sailing.
• Sailors NYCminorGTM or Marketing PartnerCross promotion partnership where Oakcliff invites Sailors NYC members to sail in Oakcliff's Dream Yacht Charter Series, and Sailors NYC invites Oakcliff Supporters to sail in New York Harbor.

Scale indicators3 records

Recent moves7 records

Expansion highlights5 records

Regional players

• Bitter End Yacht Club: Caribbean-based sailing destination offering learn-to-sail and cruising programs. Comparable in premium experiential sailing education but in a different geographic market than Oakcliff's Northeast US base.

Broad incumbents

• New York Yacht Club: Historic yacht club that fields the American Magic America's Cup challenge. Overlapping sailing ecosystem but as a member club rather than a dedicated public training center.
• US Sailing: National governing body for sailing in the US and Oakcliff's official training center partner. Operates broader athlete development pathways but does not directly deliver training programs in the same way Oakcliff does.

Direct peers

• Sail Newport: Non-profit sailing center in Newport, RI operating high-performance programs, regattas, and youth pathways with US Sailing affiliation. Closest geographic and mission peer to Oakcliff's training center model.
• Chapman School of Seamanship: Florida-based maritime training school offering sailing, seamanship, and boat maintenance programs. Comparable in providing professional-level marine skill training for career pathways.
• Annapolis Sailing School: Long-established sailing school in Annapolis, MD offering racing, cruising, and youth programs. Directly comparable as a high-performance sailing training provider serving similar youth and adult amateur-to-pro pathways.
• IYRS (International Yacht Restoration School): Non-profit marine industry school offering boatbuilding, restoration, and composite training. Already an Oakcliff partner; comparable as a marine trade training institution preparing students for marine careers.
• Storm Trysail Sailing School: Match-racing focused sailing school with strong ties to offshore and big-boat racing. Comparable in match racing training and regatta hosting format that overlaps Oakcliff's Match Racing Acorn program.
• The Landing School: Marine industry-focused school in Maine offering boatbuilding, yacht design, and marine systems programs. Comparable in workforce development mission targeting marine industry careers.

Emerging players

• North U (North Sailing School): Sailing education company offering racing, navigation, and performance sailing courses. Comparable in delivering sailing instruction, though more focused on adult recreational racers than Oakcliff's pro-pathway youth model.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks6 records

Key highlights7 records

Customer concentration

• Xx.com/OakcliffSail
• YouTubeyoutube.com/channel/UCUxBaYV5V6V9jHHWtX1Z4MA
• Facebookfacebook.com/Oakcliffsail
• Instagraminstagram.com/oakcliffsail
• LinkedInlinkedin.com/company/oakcliff-sailing-center

Revenue estimate

Valuation estimate

Number of profiles

Profiles12 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Oakcliff Sailing