Offshore Sailing School

Offshore Sailing School was founded in 1964 by Steve Colgate, an America’s Cup and Olympic sailor, and has put more than 160,000 adults through its courses since. The operation teaching under that name today is a different one from the school that built the record: it went through bankruptcy in 2025 and now runs under the new leadership of Seaworthy Academy. Its Florida home for decades was the ‘Tween Waters resort on Captiva, and that base is closed.

The two bases it teaches from now are city waterfronts. From 505 Quay Commons on the Sarasota bayfront, students work Sarasota Bay, held behind Longboat and Siesta Keys, wide enough for real passage practice without committing to the open Gulf. From the Vinoy Marina in downtown St. Petersburg it is Tampa Bay, with shipping traffic, bridge current and the sort of pilotage a charter company expects you to have seen before.

The pathway is NauticEd throughout, taught by EDU-4 certified instructors against American National Standards. Learn to Sail runs three days on the water against 20 hours of study, on keelboats 26 feet and up. The Catamaran Endorsement adds two liveaboard days on a multihull. Bareboat Certification is the long one, 53 hours of study and six days living aboard, ending in the Bareboat Charter Master credential that charter companies read, and a one-day SLC International License covers the Mediterranean chartering that asks for a licence.

The fleet is the differentiator now, and it changed along with everything else. Teaching runs on 40 to 48 foot monohulls and catamarans, Jeanneau 479s, a Fountaine Pajot Lucia 40, a Bali 4.2, with a powerboat programme alongside on 40 to 50 footers. The Colgate 26 that Steve Colgate designed, and that the U.S. Naval Academy adopted for its training fleet, belongs to the school’s history rather than its course list. Learning on 40-plus feet means the cruising tickets are taught on the size of boat a student will actually charter.