Hawaiian Airlines began to expand its footprint throughout the 1980s, as the result of intense competition on inter-island routes created by the entrance of Mid Pacific Air into the market. In 1985, the company began its first foray outside the inter-island market through charter services to the South Pacific and then throughout the rest of the Pacific using Douglas DC-8 aircraft. Despite the early successes of this new business, Hawaiian was forced to curtail its charter services when the Federal Government banned all DC-8 and B707 aircraft without hush kits from operating within the US. Hawaiian did, however, manage to gain a short exemption for its South Pacific services.
On October 27, 2008, Hawaiian announced that prior to the arrival of its new A330s, it would lease two additional Airbus A330-200 aircraft, beginning in 2011, at the same time extending the leases of two Boeing 767-300ER aircraft to 2011 (to be withdrawn from service coincident with the delivery of the A330s). Two weeks later, the airline announced the lease of an additional A330-200 for delivery in the second quarter of 2010, along with negotiating for delivery of one aircraft from the earlier lease agreement to be moved up to the same quarter. In December 2010, Hawaiian ordered an additional six A330-200 aircraft, bringing the fleet total to 15. Further lease agreements were signed with Air Lease Corporation (one aircraft), and three aircraft each from Hong Kong Aviation Capital, and Jackson Square Aviation, bringing the A330-200 fleet to 22. In July 2015, Hawaiian announced the lease of an A330-200 from Air Lease Corporation. The purchase of another A330-200 was announced in December 2016.