Bert takes 1 lucky couple on an all-expenses-paid trip of a lifetime to Jamaica. While there, they climb waterfalls, rope swing into blue waters, swim with horses and record music in Reggae legend Bob Marley's studio.

Travel Guide

Find restaurants, accommodations and activities from this episode.

Jamaica Pictures

Bert takes 2 lucky vacationers on an all-expenses-paid ...

By Land or By Sea

Bert and Austin vacationers Sara and Jake go horseback riding ...


A Trip Flipped to Jamaica

Bert takes vacationers Sara and Jake on an all-expenses-paid ...


Kingston Cricket Club

Jake and Sara play cricket with the best players on the ...


Swim With Sharks

Two unsuspecting vacationers swim with sharks in Hawaii.

Paddle Boarding

Bert takes 2 vacationers paddle boarding on the waves in Oahu.

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