The Conch Connection

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.

This 10 day mostly, free event features the unique opportunity to experience the voices, back stories, and personalities of some of the most influential and internationally-recognized singer-songwriters at some of the most famous venues across Captiva, Sanibel, Historic Downtown Fort Myers and Fort Myers Beach! And include some of the biggest names around: Brian Sutherland, Locash, Edwin McCain and about 50 more!

October 22-31, 2027

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.