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Cuba & Jamaica, 15 Days

SEVEN Nts Cuba & SEVEN Nts Jamaica

Combine Cuba and Jamaica for fun (and rum) in the sun. Enjoy a vintage car city tour and Vinales Valley exploration in Cuba. Then, enjoy Jamaica’s Half Moon Hotel and a private Appleton Rum Estate tour.

Combine Cuba and Jamaica for fun (and rum) in the sun. Enjoy a vintage car city tour and Vinales Valley exploration in Cuba. Then, enjoy Jamaica’s Half Moon Hotel and a private Appleton Rum Estate tour.

Combine Cuba and Jamaica for fun (and rum) in the sun. Enjoy a vintage car city tour and Vinales Valley exploration in Cuba. Then, enjoy Jamaica’s Half Moon Hotel and a private Appleton Rum Estate tour.

Cuba & Montego Bay, 13 Days

SIX Nts Cuba & SIX Nts Jamaica

Indulge in Caribbean bliss with a 12-night holiday in Cuba and Jamaica. Stay at Cuba's Paradisus Princesa del Mar Varadero and tour Havana in a vintage car, then relax at Jamaica’s Half Moon with a private Appleton Rum Estate tour.

Indulge in Caribbean bliss with a 12-night holiday in Cuba and Jamaica. Stay at Cuba's Paradisus Princesa del Mar Varadero and tour Havana in a vintage car, then relax at Jamaica’s Half Moon with a private Appleton Rum Estate tour.

Indulge in Caribbean bliss with a 12-night holiday in Cuba and Jamaica. Stay at Cuba's Paradisus Princesa del Mar Varadero and tour Havana in a vintage car, then relax at Jamaica’s Half Moon with a private Appleton Rum Estate tour.

Miami & Jamaica, 15 Days

SEVEN Nts Miami & SEVEN Nts Jamaica

Experience a thrilling 14-night adventure from Miami to Jamaica, including luxurious stays, a supercar drive, a private airboat tour in the Everglades, and a relaxing week at the Half Moon Hotel in paradise.

Experience a thrilling 14-night adventure from Miami to Jamaica, including luxurious stays, a supercar drive, a private airboat tour in the Everglades, and a relaxing week at the Half Moon Hotel in paradise.

Experience a thrilling 14-night adventure from Miami to Jamaica, including luxurious stays, a supercar drive, a private airboat tour in the Everglades, and a relaxing week at the Half Moon Hotel in paradise.

Las Vegas & Jamaica, 15 Days

FOUR Nts Las Vegas & TEN Nts Jamaica

Experience the best of both worlds with four nights at The Cosmopolitan Las Vegas, including a Grand Canyon helicopter trip and limousine Strip tour, followed by 10 nights of luxury at GoldenEye Jamaica with an Appleton Rum Estate experience.

Experience the best of both worlds with four nights at The Cosmopolitan Las Vegas, including a Grand Canyon helicopter trip and limousine Strip tour, followed by 10 nights of luxury at GoldenEye Jamaica with an Appleton Rum Estate experience.

Experience the best of both worlds with four nights at The Cosmopolitan Las Vegas, including a Grand Canyon helicopter trip and limousine Strip tour, followed by 10 nights of luxury at GoldenEye Jamaica with an Appleton Rum Estate experience.

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