[4] Insel Air was incorporated as a private limited liability company (Dutch: Besloten Vennootschap) on September 8, 1993.

The company also completed the IATA operational safety audit (IOSA) and joined ALTA, the Latin American and Caribbean Air Transport Association, in November 2011.

Insel Air Aruba began operating new routes to Miami, Santo Domingo, Cuba, St. Maarten, Puerto Rico, Curaçao, Caracas, Valencia, Maracaibo, Quito, Medellin and Manaus.

Insel Air and KLM Royal Dutch Airlines consolidated their cooperation with a code-sharing agreement, offering customers greater comfort and options and thereby enabling them to travel to destinations served by the two partners without having to re-check luggage.

Insel Air had also introduced Barranquilla, Colombia in June 2014 and La Romana, Dominican Republic in July 2014 from the airline's Curaçao hub.

With the acquisition of this aircraft type, new destinations in Canada, USA and South America like Argentina and Brazil could have become a serious option for the growing network of the airline.

In January 2017, after several incidents involving loss of cabin pressure, mostly involving the MD-80 aircraft, as well as the pilots refusing to take off from Sint Maarten, lead to the grounding of all of the Aruban registered (P4) aircraft that were leased to Insel Air from Insel Air Aruba by the Curaçao Civil Aviation Authority and Department of Civil Aviation in Aruba, for inspection.

[13] Due to the grounding, the airline has had to lease aircraft from other companies, including a Boeing 737-400 from USA-based Swift Air, and an Airbus A320 from Dominican Wings for its Sint Maarten-Santo Domingo flights.

[14] Other leased aircraft included an Estelar Latinoamérica Boeing 737-400 operating Barquisimeto and Caracas as well as a Fokker 70 from Fly All Ways for its Georgetown and Suriname routes.

[16] Destinations such as Barranquilla and San Juan have also been dropped as the airline continues with its measures to stabilize its route network.

[18] In regards to the recent issues, as well as most of its fleet being used by Insel Air, Insel Air Aruba has suspended its commercial services using its own flight numbers while the Department of Civil Aviation of Aruba completes inspection of its current fleet after it was said in a statement that the Department of Civil Aviation would carry out routine inspection of four of its eight aircraft simultaneously which would gradually be released back into service when compliance was verified.

The ensuing capacity shortage across both carriers has caused significant delays and cancellations with numerous enraged and unsatisfied customers.

[22] The stabilization plans, which saw the airline operating mainly to the ABC Islands and Sint Maarten, proved positive with an improved on time performance of on average 90%, with a clear increase in customer satisfaction.

During that period, InselAir received numerous requests from the market for reinstatement of a jet service because it shortened the travel time between the islands significantly to only 1.5 hours.

On June 27, 2018, Insel Air announced the addition of the Embraer E-190 Jet, leased from the Venezuelan airline Conviasa.

Although some issues were still found, work continued on getting the aircraft ready to be put back into service, with plans to re-introduce routes such as Paramaribo, Georgetown and Santo Domingo.

InselAir's CFO André Delger admitted that the Curaçao airline had experienced a 'difficult week' at the end of January and the beginning of February when both Fokker 50 aircraft were on the ground and flights were delayed or canceled.

[31] In March 2018 and June 2018, an Insel Air Fokker 50 had to make an emergency landing due to an engine failure.

[32][33] On June 14, 2018, Haiti-based Sunrise Airways and Insel Air announced that they would start cooperation on their mutual routes.

[34] The local airline InselAir could resume its operations to and from Maiquetía, Valencia and Punto Fijo in Venezuela in the short term.

On June 18, 2018, it was announced that an agreement was reached between a Curaçao delegation headed by the Minister of Finance, Kenneth Gijsbertha, and the Venezuelan Civil Aviation Authority (INAC).

The Minister of Finance traveled to Venezuela with InselAir representatives to hold meetings with Venezuelan aviation authorities that are of the utmost importance for the future and the survival of the airline.

[37] Insel Air operated scheduled flights to 22 destinations across Brazil, the Caribbean, Colombia, the United States and Venezuela from its hubs in Curaçao and Aruba.

[39] Furthermore, Insel Air was planning to introduce Antigua, Barbados and Santiago de Cali (Colombia) to its network, but later failed to fly due to financial restraints.

Since the passing of Hurricane Irma in September 2017, Sint Maarten has also been discontinued until further notice due to the destruction caused on the island.

Here is a list of aircraft types and their operators: The initial livery which was introduced on the Embraer 110s and the first five McDonnell Douglas MD80s, was a simplified livery of a white fuselage with the Insel Air logo near the front and a blue tail with a yellow curved line and two white stars representing the Curaçao flag.

The MD80s received a modified logo and a lighter blue color on the tail while the Embraers (with the exception of the first delivered aircraft) remained unchanged.

The McDonnell Douglas MD80s later received a new livery when the acquisition for the Fokker 50s were finalised and when Insel Air Aruba was established.

Later on, most of the Fokker 50s were repainted and updated with the standard livery consisting of the white fuselage featuring the Insel Air logo and the blue tail containing the three colored waves.

For Economy class, customers were offered free food and beverages, local newspapers and raffle for a chance to win back one's ticket.