The first flight by Cape Air was operated in 1989 between Boston and its province towns. It expanded its horizon over the year and now has flight to destinations like Missouri, Maine, Massachusetts, Vermont, New Hampshire, Puerto Rico, West Indies, Illinois and many other places.
- The airlines has been winning awards for a long time now. Recently, in 2014 it was among top 10 Best Airlines in the US, Condé Nast Traveler Readers' Choice Awards BVI Property & Yacht Magazine. It was awarded as the Best Airline Serving the BVI.