During the last quarter of 2006, in an effort to scale down operations for the start of Caribbean Airlines, BWIA's management cut routes such as Manchester Airport, London Heathrow Airport, New York City and Toronto, with intermediate stops at Barbados or Antigua, ceased services to and from Saint Lucia, cut its fleet to six Boeing 737-800 jet aircraft retrofitted with wingtip devices (winglets) and reduced its staff to 800, with a majority of the staff former BWIA workers now contracted.

Caribbean Airlines operated daily direct services to Miami, Toronto, New York, Jamaica (with stops in Barbados and Antigua/St.

Maarten), Guyana, Suriname and London Heathrow till May 2007 due to the ICC 2007 Cricket World Cup, all out of its hub at Piarco International Airport.

Peter Davies resigned from his position as CEO, effective 30 September 2007, but remained as a strategic advisor to Caribbean Airlines.

On 1 October 2007, Philip Saunders, Star Alliance VP Commercial, was appointed the new chief executive officer of Caribbean Airlines.

In March 2008, the airline added a daily direct service to the Simón Bolívar International Airport in Caracas, using the Dash 8 aircraft.

This route began operations on a four times per week schedule and later in July of the same year, the frequency was increased to daily service.

The aircraft was re-fitted to the standard 16/138 configuration including an extra nine inches of seat pitch in the business class cabin, due to a different galley and closet placement.

The airline also continued to serve the United States and Canada, in Miami, Fort Lauderdale, New York City and Toronto, having also established a codeshare agreement with British Airways, for services to London and beyond.

In October, the airline announced a fleet renewal consisting of fifteen (15) Boeing 737-800 Next Generation jets and nine ATR 72-600 turboprop aircraft.

On 28 October 2011, the U.S. Department of Transportation fined Caribbean Airlines $60,000 for limiting reimbursements for lost, damaged and delayed baggage to less than consumers were entitled under the Montreal Convention.

[16] On 29 March 2013, the U.S. Department of Transportation (DOT) fined the airline $100,000 for not providing passengers with an opportunity to leave a plane that was delayed on the tarmac at New York's JFK Airport for more than four hours.

In early 2016, the management of Caribbean Airlines has set as an agenda to consider replacing its ATR fleet with comparable turboprops sourced from Bombardier due to persistent reliability problems.

The former chief executive officer (CEO) Michael Di Lollo described the ATRs as "not mission capable" after they suffered from frequent AOG (Aircraft On Ground) occurrences.

The new logo retains the iconic hummingbird while infusing fluid lines and brighter hues to embody the spirit of flight, the vibrancy of Caribbean culture and connectivity within the region.

Caribbean View, a stream-to-your-device onboard entertainment system was implemented previously, but was improved on the new aircraft including personal touchscreens for Business Class Passengers.

In 2023, the airline announced that flights to Caracas, Venezuela would be restarted on a weekly basis, with frequency expected to increase.

[23] In July 2023, it was announced that new flights to Tortola, British Virgin Islands and San Juan, Puerto Rico were tentatively approved.

In October 2024, flights to both Martinique and Guadeloupe were announced for December 2024, and the airline was given further clearance from the government to acquire additional aircraft for expansions into North and South America.

[30] The airline had four designs on the tails of its de Havilland Canada DHC-8 Dash 8 regional aircraft before these twin turboprops were phased out of the fleet (9Y-WIT was not painted).

One of the designs raised controversy, due to its usage of the Balisier flower, the symbol of the former ruling People's National Movement political party.

The new logo retains the iconic hummingbird while infusing fluid lines and brighter hues to embody the spirit of flight, the vibrancy of Caribbean culture and connectivity within the region.