Puerto Rico, Air/3 Nights, From $532
Take a long weekend and visit sunny San Juan or Ponce, on the island's southern coast.
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From left: Josh Dean landed in Quito, while Mike Kessler trekked to Tokyo
(Michael Mohr, Robin MacDougall/Getty)
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His destination: Quito
Age: 36
Home base: New York City
Must-have travel item: My iPhone with Google Maps and Translator apps
Argh! What he forgot to pack: A small shoulder or messenger bag for souvenirs
Read his story >>
MIKE KESSLER
His destination: Tokyo
Age: 38
Home base: Los Angeles
Must-have travel items: My Canon Elph point-and-shoot and a Moleskine notebook
Argh! What he forgot to pack: An umbrella-but you can buy one every three feet in Tokyo
Read his story >>
SEE WHO WON!
Check out how they used their budgets and who came out on top >>