In the summers of 1998 and 1999 they completed the CYC Basic Keel Boat, Intermediate Keel Boat and Navigation Courses.

In the winter of 1999 they chartered a 31 foot Beneteau in the British Virgin Islands.

In April 2000 they purchased a 26 foot Mirage sailboat and spent 5 summers sailing Lake Erie on  weekends and vacations.

In August 2004 they purchased a bluewater cruising sailboat, a Corbin 39.  After one short summer of sailing out of  Port Dalhousie on Lake Ontario in 2005 the boat was moved to Hamilton, Ontario and renamed Toboggan.

Stephen and Nancy left their jobs in May of 2006, to prepare Toboggan for a 3+ year sailing adventure around the world.