Early history: 1968–1975 in 1985. This particular aircraft was leased from
United Airlines. The airline was established and started operations on 7 August 1968. It was formed following the Cayman Islands Government's purchase of 51% of
Cayman Brac Airways, which had been founded in 1955, from
LACSA, the Costa Rican flag carrier, and became wholly government-owned in December 1977. In 1965, Cayman Brac Airways (which was also known as CBA Airways Ltd.) was operating regional services from
Owen Roberts International Airport in
George Town, Grand Cayman, to
Gerrard Smith International Airport (since renamed
Charles Kirkconnell International Airport) on
Cayman Brac as well as to
Little Cayman via a
flag stop and also to
Montego Bay, Jamaica. International services to
Miami were operated eight times a week using a single leased
Douglas DC-6 propliner. By the late 1970s, Cayman Airways had commenced its second nonstop route to the United States, with service between Grand Cayman and
Houston George Bush Intercontinental Airport operated with a BAC One-Eleven series 500. These were the only routes flown by the carrier that did not directly serve the Cayman Islands. Cayman Airways has also operated jet service to Cayman Brac with 727-200, 737-200 and 737-400 aircraft, including nonstop flights between Cayman Brac and Miami. In 2016, it was announced that four new
Boeing 737 MAX 8 aircraft would be introduced between late 2018 and 2020, allowing for the eventual retirement of the
737-300 aircraft then operated by the airline. The airline also added one
737-800 as an interim measure as a "bridge" aircraft between the 737-300 and the new 737 MAX 8. Cayman Airways Express also introduced
Saab 340 regional turboprop aircraft between 2015 and 2016 in tandem with the eventual planned phased retirement of the
de Havilland Canada DHC-6 aircraft as a part of the overall fleet modernisation plan. On Wednesday, 8 November 2017, the retirement process of the 737-300 began, with the first aircraft being phased out. On 27 August 2018, Cayman Airways announced that they were adding
Denver, Colorado (DEN), to its list of gateways, adding that this flight would be the longest scheduled commercial flight the airline had ever operated. Cayman Airways was planning to operate these seasonal five-hour nonstop flights from Grand Cayman to Denver twice weekly, starting 2 March 2019, until August, and then resume service in December 2019. The airline stated it would be operating its new 737 MAX 8 aircraft on this service. It was also mentioned that other destinations were being considered, such as
Los Angeles,
San Francisco,
Vancouver, B.C.,
London, England, and Brazil. However, these new services would require the runway at
Owen Roberts International Airport to be lengthened. This runway lengthening project was expected to occur within the next several years. In October 2018, the first of the airline's 737 MAX 8 aircraft was on the final assembly line at the
Boeing Renton Factory in
Renton, Washington. The second 737 MAX 8 aircraft for the airline was on the assembly line at
Boeing Renton Factory in late January/early February. On 8 November 2018, the first of the airline's new 737 MAX 8 aircraft accomplished its first major test flight. Shortly after the first test flight of the airline's first 737 MAX 8, Cayman Airways issued a statement about the safety of the new aircraft and its acceptance into the airline after concerns due to a
crash of an aircraft of the same type. Cayman Airways CEO and president Fabian Whorms stated, "I can give a full assurance that our new aircraft will not be delivered or accepted unless it has thoroughly passed all required post-production flight and ground tests successfully. Cayman Airways operates within the strict parameters of a comprehensive and robust Safety Management System, and our new Boeing 737 MAX 8 aircraft will enter passenger service only after both the aircraft and the airline are in full compliance with all safety-related requirements". The airline's first 737 MAX 8 was handed over to the airline on 29 November 2018. The second was delivered on 6 and 7 March. The third was expected to be produced and delivered by September 2019. The last of the four 737 MAX 8 aircraft that were ordered by the airline was expected to be delivered in September 2020. On 2 March 2019, the airline began its inaugural service to
Denver, Colorado. This new service (flight number KX 442) was operated with the airline's new 737 MAX 8. On 10 March 2019, Cayman Airways issued a statement about the temporary suspension of the new
Boeing 737 MAX 8 aircraft after further concerns increased due to a second crash of the aircraft type operated by
Ethiopian Airlines in Africa. Cayman Airways CEO Fabian Whorms stated, "We have taken the decision to suspend operations of both our new Boeing 737 Max 8 aircraft, effective from Monday, 11 March 2019, until more information is received". He also stated, "Cayman Airways is currently working in coordination with both the Boeing Corporation and the Civil Aviation Authority of the Cayman Islands (CAACI) to monitor the investigation into Ethiopian Airlines Flight 302".
Modern history: 2020s In late January 2021, the Civil Aviation Authority of the Cayman Islands (CAACI) rescinded its airspace restriction for the 737 MAX 8. This was done following clearance by the US Federal Aviation Administration (FAA) at the end of 2020 and approval in January 2021 by the UK Civil Aviation Authority (UK CAA) and the European Union Aviation Safety Agency (EASA). Officials explained that the decision followed the approval of extensive modifications to the design of the aircraft, to how it is flown, and to pilot training. This included modifications to the aircraft's
Maneuvering Characteristics Augmentation System (MCAS), as well as other key safety changes aimed at preventing further accidents. On 10 February 2021, the Cayman Airways CEO announced the ungrounding of its own 737 MAX 8 aircraft and a “Return To Service (RTS)” plan to reestablish the aircraft back into service. In early February 2021, the Cayman Islands Pilots Association (CAPA) issued a statement regarding the reentry of the 737 MAX 8 aircraft, stating "The B737-8 is one of the safest planes to fly on". During the week of the 10 February press conference, Cayman Airways announced public viewing and walkthroughs of the newly upgraded 737 MAX 8 aircraft and watch some of the operational test flights at
Owen Roberts International Airport and
Charles Kirkconnell International Airport over the weekend. Between the first half of 2020 to the second half of 2021, Cayman Airways, like many other airlines, had taken a hit due to the
COVID-19 pandemic. However, from mid 2020 through the third quarter of 2021, Cayman Airways operated repatriation flights through the government's Travel Cayman programme. The airline returned to a reduced commercial flight schedule during the fourth quarter of 2021. On 21 October 2021, Cayman Airways cancelled its service to La Ceiba, Honduras, due to the issuance of a
NOTAM that Goloson International Airport was downgrading to a Category 6 airport. Cayman Airways had operated the 737 MAX 8 on that route.
ICAO requires airports to be Category 7 or higher for the 737 MAX 8 to operate. In March 2023, during an interview on Cayman Compass talk show
The Resh Hour, Cayman Airways CEO Fabian Whorms said that they had begun the process of looking for a third Twin Otter for its Express Fleet. He noted that they might soon replace the Saab 340B+ fleet. He stated, "Ideally, we'd like that whatever we replace it with be something that can also fulfil the mission that the Twin Otters currently fulfil for us. But that's dependent [on] what happens with the Little Cayman aerodrome." On 24 July 2023, a joint press briefing with government ministers from Barbados and the Cayman Islands as well as Cayman Airways was held. They introduced a twice-weekly direct service to Barbados, introducing the airline to Eastern Caribbean markets and, by way of Barbados, extending to more European markets. They also announced an additional two Los Angeles flights. This came nearly a month after Cayman Airways restarted flights to Panama. On 17 November 2024, Cayman Airways obtained its third Twin Otter for its Express fleet. ==Destinations==