Cliff Fitzgerald | Modern Sailing

Cliff Fitzgerald

Instructor

Cliff grew up in a family that sailed on Long Island Sound. At the age of eight he got his start at skippering and racing in a summer youth sailing program. Dinghies led to small centerboard sloops, which led to keelboats of all types ranging from twenty-two to fifty feet. By the time he was in college, Cliff was crewing on coastal passages from New York to Nova Scotia and also teaching in the same summer program he had come up in. His family continued sailing throughout, including bareboat chartering in the British Virgin Islands.

Cliff joined the OCSC instructor team in 2015, and except for the time of COVID restrictions, has been teaching ever since. He is delighted to be back in Berkeley working with the rest of the Modern Sailing team to continue growing the school's legacy of excellence in sailing instruction. 

Share This Page

  • John Boynton

    The class was terrific. I know you must get many compliments about your sailing instructors...But I must tell you that Robert is outstanding. Having taught SCUBA, I really appreciate the way he is so sensitive to all on board, dealing with each so well, knowing quickly their strengths and weaknesses making each feel special and cared for.

  • Salesforce (Ashley H.)

    Our team at Salesforce did the Corporate Regatta Team Buidling activity (August 2026). What a blast!! HIghly recommend for your next team activity. It's fun to be out on the water, but the skippers also did a great job of teaching us all the sailing basics. The race is set up well so that we all had a chance to try out different roles. We did it with 11 people across two boats but having more boats is also doable and would lead to even more competition.

  • Trudy Flores

    Captain Jeff Cathers is really cool. I had such a great time on the Farallones Day Trip. It was actually my very best day of 2020. Thank you so much for coordinating the trip.

  • Lisa Butzer Wilde

    Thumbs up to (Club Skipper) Geoff (Love) and his wife Laura. I went on my first Club Sail on Sunday, January 18, 2026. They were terrific!

  • Mike, Santa Rosa, California

    All of the courses and my instructors (JT and Stan) were extremely professional and full of knowledge and experience. I found I was able to learn from their experiences beyond the scope of the courses, and look forward to future opportunities to do so. I would highly recommend Modern Sailing to anyone.

Follow us
on Social Media