The airline was established and started operations on August 7, 1968. It was formed following the Cayman Islands Government's purchase of 51% of Cayman Brac Airways from LACSA, the Costa Rican flag carrier, and became wholly government owned in December 1977.
LACSA had been serving Grand Cayman since the mid 1950s as an intermediate stop on its route between San Jose, Costa Rica and Miami with some flights also making a stop in Havana, Cuba as well between Grand Cayman and Miami.
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 on Cayman Brac as well as to Little Cayman via a flag stop and Montego Bay, Jamaica.
According to this airline's May 1, 1965 system timetable, weekly service with a twin engine Beechcraft 18 aircraft was being operated on a routing of Grand Cayman – Little Cayman (flag stop only) – Cayman Brac – Montego Bay with an additional weekly service being flown between Grand Cayman and Cayman Brac with an intermediate stop on occasion at Little Cayman as a flag stop.
This same timetable also states that connections at Grand Cayman were available to LACSA flights operated with Douglas DC-6B prop aircraft for service to Miami and also to Pan Am flights at Montego Bay for connecting service to Miami and New York. By 1970, LACSA had introduced British Aircraft Corporation BAC One-Eleven twin jets on its San Jose, Costa Rica – Grand Cayman – Miami route.
Early on, Cayman Airways first aircraft was a single Douglas DC-3. A few months after it was formed, the airline flew its first international route to Kingston, Jamaica (KIN) using a BAC One-Eleven wet leased from LACSA.
International service to Miami (MIA) was initiated using a single leased Douglas DC-6 propliner. The July 1, 1972 Cayman Airways system timetable lists nonstop flights between Grand Cayman and Miami being operated eight times a week and nonstop flights between Grand Cayman and Kingston, Jamaica being operated five times a week with both destinations being served with BAC One-Eleven jet aircraft.
This same timetable also lists Douglas DC-3 nonstop service to both Cayman Brac and Little Cayman from Grand Cayman and also between Cayman Brac and Little Cayman with service being operated nine times a week in each direction on the three routes between the these island destinations.
By the winter of 1973, Cayman Airways was operating stretched BAC One-Eleven series 500 aircraft on both of its jet routes and was operating seventeen flights a week between Grand Cayman and Miami as well as five flights a week between Grand Cayman and Kingston.
The airline was also offering direct connecting jet service between Miami and Kingston via Grand Cayman at this time. In 1976, the airline had increased competition on the Grand Cayman-Miami route as Southern Airways was operating daily nonstop Douglas DC-9-10 jet service with LACSA continuing to serve the route as well with BAC One-Eleven series 500 flights operated four times a week.
By the late 1970s, Cayman Airways had commenced its second nonstop route to the United States with service five times a week between Grand Cayman and Houston, Intercontinental Airport (IAH) being flown with the BAC One-Eleven series 500.
In 1979, an additional BAC One-Eleven jet as well as a Hawker Siddeley 748 turboprop and a Britten-Norman Trislander STOL (short take off and landing) prop aircraft were purchased.
The airline then replaced their two BAC One-Eleven jets with Boeing 727-200 aircraft in 1982, strengthening the airline's regional and international capability, and also allowed for the introduction of first class service. Cayman Airways also operated a Douglas DC-8-52 jetliner and a leased Boeing 727-100 jet during the 1980s.
These jets were eventually replaced with Boeing 737-200 and then with Boeing 737-300 aircraft. Boeing 737-400 jetliners were operated as well. At one time or another during the 1980s, Cayman Airways offered scheduled or charter service to Atlanta, Baltimore, Boston, Chicago, Detroit, Houston, Minneapolis, Newark, New York City, Philadelphia and St. Louis as well as Kingston and Montego Bay in Jamaica.
The airline also flew nonstop at one point between Miami and Grand Turk Island and Providenciales in the Turks & Caicos Islands with Boeing 727-200 and Boeing 737-200 jetliners. These were the only routes flown by the carrier that did not directly serve the Cayman Islands.
Cayman Airlines has also operated jet service into Cayman Brac over the years with Boeing 727–200, Boeing 737-200 and Boeing 737-400 aircraft, including nonstop flights between Cayman Brac and Miami, and currently continues to do so with Boeing 737-300 jets.
Besides nonstop flights to several destinations in the U.S., the airline currently operates nonstop jet service between Grand Cayman and Havana, Cuba, Kingston, Jamaica, La Ceiba, Honduras and Montego Bay, Jamaica. Non-jet flights between Grand Cayman, Cayman Brac and Little Cayman are currently operated with turboprop aircraft by Cayman Airways Express.
The airline struggled throughout the early 1990s; however, financial assistance from the Cayman Islands Government, financial re-structuring, newer, more modern aircraft and the addition of new destinations such as Chicago, Dallas/Ft. Worth (both served on a seasonal basis) and Havana, Cuba appear to have helped the airline.
The company's mascot is an embellishment of the original Sir Turtle designed by Suzy Soto. As first designed, Sir Turtle did not have the red flying scarf. That original design was used on baggage stickers by Cayman Islands Customs and also became the logo of the Department of Tourism which was then headed by Eric Bergstrom.
Mrs. Soto was married to Eric Bergstrom, with whom she built the Tortuga Club on the East End of Grand Cayman. The red flying scarf was later added to Sir Turtle in 1978 by Capt. Wilbur Thompson, the Chief Pilot of Cayman Airways at the time, and that modified Sir Turtle became the airline's new logo.
Cayman Airways largely serves major regional cities in the United States, Jamaica, Cuba and Honduras. All outbound jet flights originate at Owen Roberts International Airport on Grand Cayman Island and often remain on the ground at the destination city for a short time prior to returning inbound to Grand Cayman.
Because Owen Roberts International Airport does not have jet bridges, all passengers are routed to and from the terminal building onto the ramp for access to the aircraft using new state of the art boarding ramps, which allow passengers to walk on and off the aircraft without stairs.
These ramps also allow passengers with limited mobility, including those in wheel chairs to have much easier access to the aircraft. Upon arrival to most of the international destinations,the aircraft is able to utilize a jet bridge service for deplaning and boarding. All Cayman Airways jet flights permit economy class passengers to check up to two pieces of baggage (up to 55 pounds) without charge, and all flights feature complimentary Tortuga rum punch—a signature cocktail of the Cayman Islands.
According to the June 18, 1991 Cayman Airways system timetable, the airline was serving the following destinations with scheduled nonstop flights primarily to and from Grand Cayman (except where noted):
- Atlanta, Georgia – service operated via an intermediate stop in both directions in Tampa
- Cayman Brac, Cayman Islands
- Grand Cayman, Cayman Islands – airline headquarters and hub
- Grand Turk, Turks & Caicos Islands – service to and from Miami
- Houston, Texas – Intercontinental Airport (IAH)
- Kingston, Jamaica –
- Little Cayman, Cayman Islands
- Miami, Florida
- New York City, New York – John F. Kennedy Airport (JFK)
- Providenciales, Turks & Caicos Islands – service to and from Miami
- Tampa, Florida
According to the Official Airline Guide (OAG), by the fall of 1991 Cayman Airways was primarily operating Boeing 737-400 jetliners with some flights also being operated with Boeing 737-200 jets. Service to Cayman Brac and Little Cayman was being operated with commuter prop aircraft.
The airline also had substantial competition on their core Grand Cayman-Miami nonstop route at this same time: Cayman Airways was operating nineteen flights a week, all with Boeing 737-400s, while American Airlines was operating seven flights a week with Boeing 757-200 jetliners, Pan Am was operating five flights a week with Boeing 727-200 jets and Northwest Airlines was operating ten flights a week with McDonnell Douglas DC-9-30 twin jets.
Thus, there were a total of 41 round trip flights a week being operated with mainline jet aircraft between Grand Cayman and Miami at this time.
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