Top Caribbean Charter Airlines

How to book a charter flight in the Caribbean islands

Charter airlines play a key role in Caribbean travel, filling gaps in local air service (particularly to smaller islands) as well as delivering tourists to out-of-the-way destinations and resorts. Charter prices can be competitive with scheduled airline service in the Caribbean, especially for groups.

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    ••• Air America King Air E90. © Air America
    Destinations: Based in Puerto Rico, this Air America (not the CIA one!) offers service throughout the Caribbean, including St. Barths, Culebra, Vieques, St. Thomas, Virgin Gorda, Tortola, St. Croix, Anegada, Anguilla, St. Maarten, and San Juan.

    Reservations: 787-276-5669

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    "Improving the Experience" 

    Destinations: 3-plane fleet with service to Dominican Republic, Puerto Rico, Haiti. Coming soon: flights to Aruba, San Juan Puerto Rico, San. Martin, Cuba, and more. 

    Reservations: 809-826-4222

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    Destinations: Imagine getting from Montego Bay to Negril in just 12 minutes -- it can be done with this Jamaican charter airline, which also provides air service to Kingston, Ocho Rios, and Port Antonio via Cessna 208B Grand Caravans and other aircraft.

    Reservations: 876-940-6660

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    Destinations: Based in U.S. Virgin Islands and offers turbo-prop and jet service throughout the Caribbean and to North, Central and South America. Voted top airline in the Caribbean in 2012, 2013, and 2015 by ProPilot PRASE survey. 

    Reservations: 340-778-9177

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    "Flying is an art...the Caribbean is our canvas!" 

    Destinations: Private flights to and from Beef Island Airport (EIS) from Tortola, Virgin Gorda, Anegada, San Juan, Puerto Rico, St. Thomas - US Virgin Islands, St Maarten, Antigua, Anguilla and other destinations, via  twin engine Piper Navajo prop planes.

    Reservations: 284-495-6000

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    Destinations: Turks & Caicos charter airline also offers scheduled service to Grand Turk, Providenciales, and Salt Cay, as well as Haiti. Check in is 40 minutes prior to departure, with flight doors closing 20 minutes before take-off. 

    Reservations: 649-941-5730

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    "The Caribbean's Premier Charter Airline" 

    Destinations: Daytrips to Anegada are a specialty of this British Virgin Islands charter airline, which also offers service throughout the Caribbean on Piper Navajo and Piper Navajo Chieftain planes. As the website explicitly states, "your schedule is our schedule," and when booking with four or more people, these charters end up being less expensive in most cases than non-chartered air travel. 

    Reservations: 284-495-2002

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    Destinations: Travel the skies of the British Virgin Islands like Richard Branson does -- by charter copter. Antilles Helicopter Service offers sightseeing flights to the BVI and St. Maarten as well as VIP transportation. Other tours of the islands are also available for a relatively cheap rate per person.

    Reservations: 284-495-2538

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    Destinations: The official airline of St. Vincent and the Grenadines also offers VIP charter flights to the Grenadines, Barbados, St. Lucia, Grenada and Montserrat. Services include chartered flights as well as scheduled flights. 

    Reservations: 800-624-1843

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    "Jamaica's Number One Air Taxi" 

    Destinations: Montego Bay based charter flies throughout Jamaica, based at Sangster International Airport. 

    Reservations: 876-952-2516

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    More Airline Options for Reaching the Caribbean