Jamaica 🪘 in $240s-$390s RT

Jamaica 🪘 in $240s-$390s RT

There are dozens of bars by the ocean in Jamaica, but I'll do you one better — How about a remote bar on the ocean, an entire mile away from the shore?

Here's what you're gonna do: Head to the island's southern coast. There's not really a town to look for, but you'll be about halfway between Black River and Treasure Beach. If you feel like you're lost in the jungle, you're probably on the right track.

Find the correct stretch of sand, and you'll start seeing signs that advertise boats to the "Pelican Bar." Choose from the captains offering rides, arrange your time, and set sail.

What awaits you at the end of this journey? Perhaps the most "Caribbean" place in existence: a bar made of haphazard planks and logs that looks like it's about to collapse into the ocean, where you can enjoy excellent fresh-caught seafood and an array of cocktails while watching turquoise waves undulate beneath you.

Now THAT'S a real Caribbean vacation :-)

Taking off ✈️

Tip Published: Oct 21, 2025

Round trips to Kingston (KIN):

  • Miami (MIA) - $287 (cabin bag, up to $332)
  • New York (JFK) - $391 (cabin bag)
Round trips to Montego Bay (MBJ):

  • Baltimore (BWI) - $383 (cabin bag)
  • Chicago O'Hare (ORD) - $357 (cabin bag)
  • Fort Lauderdale (FLL) - $277 (cabin bag)
  • Miami (MIA) - $277 (cabin bag)
  • New York (JFK) - $355 (cabin bag)
  • Newark (EWR) - $355
  • Tampa (TPA) - $240 (up to $280)
Round trips to Ocho Rios (OCJ):

  • Miami (MIA) - $353 (cabin bag)
Flight Details

Travel Dates

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Airline

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Standard Fare

$400 - $500 (non-stop)

Bags & Fees

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Flight Notes

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How to Book

    This is a Takeoff-only Flight for Jack's Flight Club Takeoff members only. For step by step instructions on how to book it you'll need to login or upgrade to Takeoff membership.