Offshore Sailing School President and CEO, Doris Colgate, announced today that the company’s popular resort-based sailing courses will start March 1, 2023, at Tween Waters Island Resort & Spa on Captiva Island, Florida. “We’ve known and respected the owners and management of Tween Waters Island Resort for many years. Now our clients have the opportunity to enjoy all this destination resort has to offer while learning to sail or bareboat charter.” Colgate added, “Offshore Sailing School is thrilled to welcome visitors and residents back to Sanibel-Captiva Islands and support other businesses welcoming guests to the beaches, islands, and neighborhoods of Fort Myers and the greater Southwest Florida area.”

On September 28, 2022, Hurricane Ian caused significant damage to marinas at three of the company’s six locations in Southwest Florida: Captiva Island, Ft. Myers Beach, and Cape Coral. Since then, the company has repaired its fleet and hired additional instructors. The company has also added a new Jeanneau 440 cruising yacht and Lagoon 40 catamaran to its Florida fleet, in addition to placing another Moorings 4500 catamaran at Scrub Island Resort, Spa & Marina in the British Virgin Islands. The company also teaches its power catamaran certification course from The Moorings base on Tortola in the British Virgin Islands.

In Florida, Offshore Sailing School already teaches a full roster of US Sailing certification courses at its St. Petersburg, Florida, location and is poised for growth with the addition of its newest Florida location on Captiva Island. Tween Waters is a full-service resort with a variety of accommodations, direct access to a sugar-sand beach to the west, and the natural beauty of Pine Island Sound to the east. At Tween Waters, the company will offer Learn to Sail, Performance Sailing, and Fast Track to Cruising® course vacation packages for adults and families, plus sailing lessons for resort guests, and group team building events. Students receive textbooks to study in advance, with US Sailing certification available at each level. In its most popular, week-long Fast Track® to Cruising course, students qualify as skippers, competent and confident to handle cruising boats up to 50’ on their own. The company also offers advanced Navigation and Passage Making courses for avid sailors.

Offshore Sailing School’s relocated Headquarters office is at 6338 Presidential Ct., Ste. 201, Fort Myers, Florida, 33919.

Offshore Sailing School continues to hire qualified instructors for its sailing and powerboating courses at all locations. Interested candidates should email US Regional Manager, Randon Finkelstein, [email protected].

America’s #1 Sailing School® currently operates at resort locations in Florida and the British Virgin Islands, offering all levels of US Sailing and Powerboating certification courses, team building and leadership development programs. Visit