Make your Valentine feel as special as he or she is! Make memories in Key West by starting aboard the Key West Express. Visitors are drawn to the southern charm and Caribbean influences of this laid-back island city, only 4 miles long by 1.5 miles wide. During the day or at night, the island is alive with sidewalk cafes, world-class restaurants, fishing, watersports, shopping, performing arts, musical entertainment and galleries before the island gathers each evening at Mallory Square for the world renown sunset celebration.
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There are plenty of places to watch a ball drop. Key West, naturally, has a few more colorful ideas. On Thursday, December 31, 2026, you can ease into the evening with a famous sunset, then ring in the new year with a giant red shoe, a glowing conch shell or a pirate wench descending from a schooner mast—all within a short Old Town walk of one another.
That wonderfully odd mix is exactly why New Year's Eve here is so much fun. The air is warm, the streets are lively and a simple midnight countdown turns into a story you will be telling long after you have traded flip-flops for winter boots. The island's current New Year's Eve event guide confirms the big three celebrations, but individual venue details can change, so check the official pages before you head out.
Key West Race Week Has a Sound All Its Own
First comes the rumble. Then the spray, the bright race boats and the kind of crowd that knows something very loud and very fast is about to happen. Key West Offshore World Championship Week turns the island into a playground for offshore-racing fans, curious first-timers and anyone who enjoys a little extra buzz with their sunshine.
From November 1–8, 2026, the championship brings world-class teams, waterfront viewing and plenty of reasons to linger after the engines quiet down. You do not need to know the difference between a catamaran and a V-bottom to have a great time. Just bring your sunglasses, a little patience for a lively island and a healthy respect for horsepower.
Before Key West became famous for sunset celebrations, colorful characters and tropical escapes, it was known for something else: cigars. In the late 1800s, Cuban tobacco, Cuban craftsmanship and Key West's location just 90 miles from Cuba helped turn the island into one of the nation's most important cigar-manufacturing centers.
That history is still woven into the streets of Old Town. Travelers arriving aboard Key West Express step ashore near the Historic Seaport, within easy reach of neighborhoods and landmarks shaped by the island's close relationship with Cuba.
October 16-25, 2026
What Is Key West Fantasy Fest?
Every October, Key West transforms into one of the most exciting destinations in Florida during Fantasy Fest. This annual 10-day celebration is famous for its elaborate costumes, lively parades, themed parties, live entertainment and unmistakable island spirit.
