Cayman Airways made its inaugural flight on August 7, 1968, carrying passengers from Grand Cayman to Cayman Brac. Fifty-seven years later, the airline is celebrating that milestone with an anniversary sale that cuts fares on most of its network — including the domestic routes that still link the three Cayman Islands today.
Cayman Airways operates more nonstop international jet flights to and from the Cayman Islands than any other airline.
This sale delivers discounted fares on key routes for fall travel, but the booking window is tight — August 1–11, 2025 — and the travel period excludes peak holiday weeks. If you’ve been eyeing a September-to-December trip to the Cayman Islands, this is the moment to lock in a price.
Budget travelers
Island hoppers
Families
Below is a quick look at what’s on offer, followed by the route details, a bit of airline history, and what makes the sister islands worth the short flight.
| Destination | Route Type | Travel Window |
|---|---|---|
| Miami, Tampa | International (Florida) | Sept 8 – Dec 12, 2025 |
| New York (JFK) | International | Sept 8 – Dec 12, 2025 |
| Los Angeles (LAX) | International | Sept 8 – Dec 12, 2025 |
| Kingston, Havana | International | Sept 8 – Dec 12, 2025 |
| La Ceiba, Panama City | International | Sept 8 – Dec 12, 2025 |
| Cayman Brac, Little Cayman | Domestic | Sept 8 – Dec 12, 2025 |
Paul Tibbetts, the airline’s executive vice president of commercial affairs and chief financial officer, said the sale “is our way of expressing heartfelt thanks to our loyal customers and those who have traveled with us recently.” The airline is also using the anniversary to underscore its commitment to the community it has served for nearly six decades.
Sale Details: what’s included and when
The 57th anniversary sale runs from August 1 to August 11, 2025. Travel must take place between September 8 and December 12, 2025 — a window that covers late summer through early winter, but excludes the Christmas holiday spike.
International routes on sale include Grand Cayman to Miami, Tampa, New York (JFK), Los Angeles (LAX), Kingston (Jamaica), Havana (Cuba), La Ceiba (Honduras), and Panama City (Panama). Domestically, the sale applies to flights from Grand Cayman to Cayman Brac and Little Cayman.
For Florida routes, the sale has specific northbound and southbound travel windows. Northbound (Cayman to Florida): October 16–20, November 6–7, November 27–28. Southbound (Florida to Cayman): October 23–26, November 9–10, November 28–30. For Los Angeles and New York, northbound travel is November 29–30, southbound November 20–24. Confirm these exact dates at booking.
Reservations can be made online at caymanairways.com, through the airline’s mobile app, or via local travel agents. Phone booking is also available: 949-2311 (local), 1-800-422-9626 (toll-free USA), 866-759-1372 (toll-free Jamaica), 800-2791-9422 (toll-free Honduras), and 800-0195 (toll-free Panama).
Routes on sale: where you can fly for less
The sale covers the airline’s full route map, from the short hop to Little Cayman to transcontinental flights from Los Angeles. Below are the specific city pairs with discounted fares.
A brief history: fifty-seven years of connecting the Cayman Islands
Cayman Airways Limited (CAL) was established in 1968 and launched its first flight on August 7 of that year — a 30-minute hop from Grand Cayman to Cayman Brac. That single route has since grown into a network spanning the United States, Cuba, Jamaica, Honduras, and Panama.
Today the airline’s fleet includes Boeing 737-8 aircraft, and it offers more nonstop international jet flights to and from the Cayman Islands than any other carrier. The anniversary sale is a chance to experience that connectivity — especially the domestic legs that make the three-island nation feel smaller than its geography suggests.
Sister islands: Cayman Brac and Little Cayman
Most visitors land in Grand Cayman and never leave. But the sale makes it cheap to change that. Cayman Brac and Little Cayman lie roughly 90 miles northeast of Grand Cayman, each with a character distinct from the main island’s resort corridor.
How to book and travel tips
Book directly on the Cayman Airways anniversary sale page between August 1 and August 11, 2025. The sale fares are available only for travel between September 8 and December 12, 2025, and some routes have additional date restrictions (see the Florida and long-haul windows above).
If you’re planning activities beyond the flight, consider booking tours in advance — especially popular snorkeling and diving excursions. For example, you can browse Cayman Islands snorkeling tours on Viator to get a sense of options and prices before you arrive.
Heads up: some links here are affiliate links — costs you nothing extra. As an Amazon Associate, we earn from qualifying purchases.
Cayman Airways’ mobile app allows you to book sale fares and manage reservations. For the domestic routes to Cayman Brac and Little Cayman, booking directly on the website or app avoids any third-party fees.
Before you go — Cayman Airways 57th anniversary sale
When is the sale?
The sale runs from August 1 to August 11, 2025. Book within these dates to get the discounted fares.
Travel must occur between September 8 and December 12, 2025. No bookings outside that window qualify.
Which routes are included?
International routes: Grand Cayman to Miami, Tampa, New York, Los Angeles, Kingston, Havana, La Ceiba, and Panama City. Domestic routes: Grand Cayman to Cayman Brac and Little Cayman.
Some Florida and long-haul routes have specific northbound/southbound travel windows — check the table above before booking.
Can I book domestic flights to the sister islands?
Yes. The sale applies to Grand Cayman–Cayman Brac and Grand Cayman–Little Cayman for the full September 8–December 12 window with no extra date restrictions.
These short flights are a cheap way to add a second island to your trip — the fare is often lower than a taxi ride across Grand Cayman.
What are the travel date restrictions for Florida routes?
Northbound (Cayman to Florida): October 16–20, November 6–7, November 27–28. Southbound (Florida to Cayman): October 23–26, November 9–10, November 28–30.
These windows are narrow, so plan your itinerary around them if you’re flying from Miami or Tampa.
Is the sale available for travel over Thanksgiving?
Partially. For Florida routes, the November 27–28 northbound and November 28–30 southbound windows overlap with the U.S. Thanksgiving holiday. For New York and Los Angeles, the southbound window (November 20–24) and northbound window (November 29–30) also bracket the holiday.
Availability may be limited on those dates — book early.
Fifty-seven years and counting
That first flight in 1968 carried passengers from Grand Cayman to Cayman Brac on a route that still operates today. Fifty-seven years later, the same airline connects the Cayman Islands to eight international destinations and keeps the three islands linked with daily domestic service. The anniversary sale is a reminder that the airline’s real value isn’t just the price of a ticket — it’s the fact that you can island-hop across this country in under an hour. For more on how the Cayman Islands are expanding air service, see our coverage of new flights making Grand Cayman easier to reach.
References
Cayman Compass. “Cayman Airways celebrates 57 years with an airfare sale.” 2025. ↗
Cayman Independent. “Cayman Airways marks 57 years of flying with anniversary sale.” 2025. ↗
Caribe Vibes. “Celebrate 57 years of Cayman Airways with travel deals.” 2025. ↗
For more on traveling to the Cayman Islands, check out our guide to the islands’ new tourism campaign and the latest on Spirit Airlines’ new Fort Lauderdale–Grand Cayman route. These posts cover additional airlift options that pair well with the anniversary sale fares.
Explore Places to Stay in Cayman Islands
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