In 1990, Wilson acquired and re-fitted the 60' trimaran Great American toward his first project. He sought a project long enough to allow for bringing in all the disciplines desired, dramatic enough to arouse media attention, and uncertain enough to keep the outcome in doubt. He decided to tackle the sailing record from San Francisco to Boston by way of Cape Horn set during the California Gold Rush by the clipper Northern Light. A Teacher's Guide was written and distributed to several hundred schools who also received a newsletter with information from the boat and access to a daily telephone recording from the boat.

The project was a success in the classroom and a disaster at sea, as Wilson and his co-skipper Steve Pettengill were capsized on Thanksgiving Day 1990 in 65' seas 400 miles short of treacherous Cape Horn. The boat was upside down for an hour, and then was re-righted by a wave, the first re-righting of a capsized trimaran by a wave in recorded history. A dramatic midnight rescue by the giant containership New Zealand Pacific was chronicled in Reader's Digest. Wilson and Pettengill went to Holland with NZP and returned home to Boston. (GAII was lost, to fetch up in good company a year later on South Georgia Island, only miles from where Sir Ernest Shackleton landed.) In subsequent school visits in the Boston area, it was evident that the kids loved having something real coming into their classrooms. The enthusiasm of the kids was what prompted Wilson to decide to try it again.

In 1993, having raised funds to acquire another trimaran, and having persuaded 12 major newspapers to publish an 11 part series that he would write from the boat for kids to read, and having persuaded Prodigy to produce the first interactive learning adventure, he set out again from San Francisco, and with co-skipper Bill Biewenga, survived Cape Horn and broke Northern Light's record, arriving in Boston in 69 days 20 hours. There the sailors were greeted by a thousand schoolchildren of the 1/3 million who had followed the adventure through the newspapers and Prodigy.

The Ocean Challenge concept was proven.

Subsequent projects early on included an interactive learning adventure with the U.S. Women's Challenge, a team entered into the 1993-4 Whitbread 'Round the World Race. And in 1994-5, Ocean Challenge developed a science and technology program off one of the America's Cup syndicates. The program, Young America: Defending the America's Cup, was the first interactive education program on the fledgling World Wide Web, and ran through the NIE channels of 27 newspapers. The concept was confirmed.

Deciding that a business could not be permanently run if dependent on 'made-for-online' adventures, or occasional events such as the Whitbread Race or America's Cup, Ocean Challenge turned to work with real field schools, accredited academically, but in settings which were extraordinary adventures unto themselves. Thus began the series of partnerships which has evolved into sitesALIVE!, a menu of programs, running concurrently, and which link students to their student peers, on fascinating adventures and expeditions worldwide.