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Caribbean Sun can trace it's roots back to Caribbean Star Airlines, which is owned by texan Allen Stanford. Caribbean Star grew steadily throught the 1990s, becoming a small international airline that provides services around Caribbean countries. Caribbean Sun grew out of neccesity to add more frequencies on certain Caribbean Star destinations, and to add new destinations to Caribbean Stars route system. In essence, then, Caribbean Sun Airlines is a division of Caribbean Star.
In February of 2003, Caribbean Sun inaugurated flights from Luis Munoz Marin International Airport in San Juan to Tortola's airport, using DASH-8 planes, a type which is also a staple on Caribbean Stars fleet.
All white fuselage with the name Caribbean Sun in green near the cockpit, below the passenger windows. Sunshine yellow tail, with the green Caribbean Sun logo on it. Their livery reflects that of parent company Caribbean Star.