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Win a once in a lifetime family beach vacation in Pensacola Florida

Last updated 29th May 2025

Enter our contest to win a family beach vacation in Pensacola Florida, officially known as  The Way to Beach™. If you want to know what that means, enter our contest to win a 7-day family vacation, with return flights from Canada and accommodations.

Win a Family Beach Vacation in Pensacola Florida.

Take the Pensacola Quiz, find your own personal Way to Beach™ and enter our contest.

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Gulf Islands National Seashore, Pensacola

Start your dream vacation on dreamy beaches

It’s been said that there’s something magical about Pensacola’s beaches. In fact, locals claim that simply stepping on to the sands calms you. However, with everything from eco-trails and watersports, festivals and family activities, they go well beyond a soul-soothing effect. None other than USA Today named Pensacola Beach, ‘The Best Beach in Florida’, and then it went on to name the Gulf Islands National Seashore, ‘Best Florida Attraction’.

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Downtown Pensacola

Discover why Pensacola is called Festival City of the South

Pensacola goes by a few names and all of them flattering and well-deserved. Over the centuries the flags of Spain, Britain, France, the Confederacy and the US have flown over the city, hence the name City of Five Flags. However, the more recent title, Festival City of the South comes directly from the deep spirit of good-time that runs right through Pensacola 365-days a year.

If you win a family vacation in Pensacola you could visit in February and catch beads and brilliant vibes at one of America’s original Mardi Gras celebrations. There are Bands on the Beach from April to October every year. And it’s eyes to the skies in July for the Blue Angels Air Show. September is the month for the ridiculously delicious annual Seafood Festival . And the one and only Foo Foo Festival is end-to-end Pensacola culture for 14 days and nights in November.

How to win a family beach vacation in Pensacola

 

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