Win a Trip for Two to the Florida Keys

Deadline: 9/7/2026

Spend your days exploring the colorful streets of Key West.

Visit the famous Southernmost Point, just 90 miles from Cuba.

Walk through Ernest Hemingway's historic home.

Meet the descendants of his legendary six-toed cats.

Watch boats drift through the water.

Discover hidden beaches.

Enjoy fresh seafood at waterfront restaurants.

And every evening, join locals and travelers alike for the famous Key West Sunset Celebration.

Performers, musicians, artists, and visitors gather to watch the sun disappear into the Gulf of Mexico.

Looking for adventure?

Explore Dry Tortugas National Park, home to a massive 19th-century fortress sitting in the middle of the ocean.

Snorkel above vibrant coral reefs.

Search for sea turtles.

Experience a side of Florida that most visitors never see.

The Grand Prize includes:

✓ Round-trip airfare for two

✓ Hotel accommodations

✓ Spending money

✓ An unforgettable Florida Keys getaway

And that's not all.

Four monthly winners will also receive:

✓ A $1,000 Nautica Gift Card

✓ A Nautica suitcase

✓ The perfect excuse to start planning their next adventure

Whether you're dreaming of island hopping, ocean views, legendary sunsets, or simply escaping everyday life for a few days, this could be the trip you've been waiting for.

No purchase necessary.

Simply enter your name and email address for your chance to win.

One Grand Prize winner and four monthly prize winners will be selected.

The giveaway ends September 7, 2026.

Enter today and start imagining your Florida Keys adventure.