The Trip is an annual, once-in-a-lifetime getaway that one lucky winner will experience. Discover all of the past places from this amazing sweepstakes.

2018: Antigua + St. Lucia

Horseback Riding
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Horseback Riding

02:00
Jack Maxwell and Kellee Edwards explore Antigua's scenic trails and coastline on horseback.

Plan Your Caribbean Getaway

Top 10 Reasons to Visit Antigua 10 Photos

Where to Stay, Eat and Play in St. Lucia

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2017: Florida + Jamaica

Jet Packing in Miami
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Jet Packing in Miami

03:06
Jack Maxwell and Samantha Brown strap on jet packs in Miami to try walking on water -- and flying above it.

Stunning Sights of Jamaica 12 Photos

Honeymoon Escapes 12 Photos

2016: Caribbean Islands

The Trip 2016: Caribbean
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The Trip 2016: Caribbean

01:02
Enter daily to win a trip of a lifetime worth $100,000 to the Caribbean!

Escape to the Caribbean 11 Photos

St. Lucia's Adventures 12 Photos

21 Hottest Caribbean Escapes 21 Photos

2015: Hawaii

Waimeas Merriman's Restaurant
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Waimeas Merriman's Restaurant

01:25
Sam samples the best of Hawaiian cuisine at Merriman's, a pioneer in the farm-to-table movement.

Oahu

Kauai

Lanai

2014: Spain + Morocco

Places to See in Barcelona 19 Photos

Casablanca's Subtle Charm 10 Photos

Madrid's Top 10 Attractions

The Beauty of Madrid 17 Photos

Marrakech’s Vibrant Flair 13 Photos

2013: Croatia + Italy

Explore Naples 13 Photos

Beautiful Croatia 13 Photos

The Allure Italy 11 Photos

Rome's Must-Do List 13 Photos

Croatia's Sexiest Beaches