jetBlue expanded service to the Caribbean, including to St. Maarten and Puerto Plata commencing January 10, 2008. With these additional destinations, jetBlue serves a total of twelve Caribbean/Atlantic destinations including Aruba; Barbados; Bermuda; Cancún; Nassau; Aguadilla; Ponce; San Juan, Puerto Rico; Santiago; and Santo Domingo, Dominican Republic.
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In July 2016, jetBlue announced commercial flights from the United States to Cuba will commence in late August. On August 31, 2016, JetBlue Flight 387 from Fort Lauderdale–Hollywood International Airport to Abel Santamaría Airport, in Santa Clara, became the first scheduled commercial flight between the United States and Cuba in 55 years. Only charter flights were allowed under previous rules, which required that passengers had to arrive more than 4 hours before the scheduled departure and often endure long lines for documentation checks, late flight arrivals, and pay high baggage fees.
jetBlue experienced its first-ever quarterly loss during the fourth quarter of 2005 when the airline lost $42.4 million, enough to make them unprofitable for the entire year of 2005. The loss was the airline's first since going public in 2002. JetBlue also reported a loss in the first quarter of 2006. In addition to that, jetBlue forecasted a loss for 2006, citing high fuel prices, operating inefficiency, and fleet costs. During the first quarter report, CEO David Neeleman, President Dave Barger, and then-CFO John Owen released JetBlue's "Return to Profitability" ("RTP") plan, stating in detail how they would curtail costs and improve revenue to regain profitability. The plan called for $50 million in annual cost cuts and a push to boost revenue by $30 million. jetBlue Airways moved out of the red during the second quarter of 2006, beating Wall Street expectations by announcing a net profit of $14 million. That result was flat when compared to jetBlue's results from the same quarter a year before ($13 million), but it was double Wall Street forecasts of a $7 million profit, Reuters reports. The carrier said cost-cutting and stronger revenue helped it offset higher jet fuel costs. In October 2006, jetBlue announced a net loss of $500,000 for Quarter 3, and a plan to regain that loss by deferring some of their E190 deliveries and by selling 5 of their A320s.
jetBlue previously had its headquarters at 80–02 Kew Gardens Road, and then in the Forest Hills Tower, both in Forest Hills, Queens, New York City, 6 miles (9.7 km) from the current office in Long Island City. In 2001 the airline had announced that it wanted to take 74,000 square feet (6,900 m2) of space in the Forest Hills Tower, and by December 2002 announced that it planned to increase its leased space.
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