About Us, Celebrating 60 Years!

STEVE PHOTO

Steve Colgate

FOUNDER & CHAIRMAN

Steve Colgate, a luminary in the sailing world, has dedicated his life to promoting sailing through education, innovation, and competitive racing. As the founder and president of Offshore Sailing School, Steve left an indelible mark on the sport, inspiring countless individuals to embrace the sea.

FOUNDING OFFSHORE SAILING SCHOOL & DESIGNING THE COLGATE 26

In 1964, Steve co-founded the Offshore Sailing School with his wife, Doris Colgate. Their vision was to provide top-notch sailing instruction for all skill levels. Steve has co-authored several sailing books with Doris, including “Fast Track to Cruising” and “Bareboat Sailing: The National Standard for Quality Sailing Instruction.” His mentorship has shaped the careers of many sailing professionals. A significant contribution to sailing is Steve’s design of the Colgate 26 sailboat. In collaboration with naval architect Jim Taylor, Steve created a boat known for its speed, safety, and ease of handling. The Colgate 26 is widely used in sailing schools and clubs, for training and racing.
Read more.About Us New

DORIS PHOTO

Doris Colgate

CEO & PRESIDENT

Doris Colgate, a pioneer in the sailing industry, co-founder and CEO of Offshore Sailing School, has significantly advanced sailing education and empowered women in the sport. Her journey reflects her passion, commitment, and unwavering dedication to excellence.

OFFSHORE SAILING SCHOOL & ADVOCACY FOR WOMEN IN SAILING

In 1964, Doris co-founded Offshore Sailing School with her husband, Steve Colgate. The school aimed to provide high-quality sailing education to enthusiasts of all levels. Under her leadership, the school expanded from a single location in New York City to multiple locations across the United States and the Caribbean. Recognizing the need for more opportunities for women in sailing, Doris launched the National Women’s Sailing Association (NWSA) in 1990. She also initiated the Women’s Sailing Conference, an annual event designed to empower women through hands-on sailing experiences and workshops, fostering a sense of camaraderie and support among women sailors.
Read more.About Us New

RANDON PHOTO

Randon Finkelstein

CHIEF OPERATING OFFICER

Randon Finkelstein, from Houston, Texas, discovered sailing at age 12 and quickly advanced from instructor to COO. A US Sailing National Faculty member and certified instructor, Randon holds multiple licenses, and with over 30,000 nautical miles sailed, he inspires sailors worldwide.

BETH PHOTO

Beth Oliver

VP & DIRECTOR OF SALES & MARKETING

Beth brings over 25 years of experience with major corporations and entrepreneurial ventures, including General Motors, Disney, and Warner Bros. She managed high-profile sponsorships and events, and was elected to the Sail America Board of Directors in 2023.

JOSH PHOTO

Josh Julow

VP & DIRECTOR OF REVENUE & LOGISTICS

Josh Julow, a Metro-Detroit native, swapped fresh water for salt water in 2014. A Marquette University graduate, he started at OSS as Sales & Marketing and later managed operations. After a time at Rice Windows and Doors, he returned driven by his love for water and adventure.

REPUTATION, QUALITY, PROFESSIONALISM & EDUCATIONAL EXPERTISE.

We are America’s #1 Sailing School

LEADERS & EMPLOYEES WITH VAST EXPERIENCE AT ALL LEVELS

About Us New ENJOY OUR #DOCKSIDECHATSWITHSTEVE

SAILING NEWS

Receive news & specials in our “Sailing News” E-Newsletter.

SIGN-UP

OSS BROCHURE

Find out more about all our courses and offers available

DOWNLOAD

CONTACT US

Have a question? We’re here to help, whenever you need us.

CLICK HERE

PROTECT YOUR INVESTMENT WITH TRAVEL INSURANCE

Call Us Today!

GET IN TOUCH, ASK OUR EXPERTS ABOUT TRAINING, GROUP PACKAGES, VACATIONS, AND MORE!

888.454.7015

Toll-free US and Canada

phone white
239.454.1700

Local and International

phone white