The Conch Connection

Florida's southwest coast may be better known for sunshine, beaches and waterfront sunsets, but its historic downtowns take on a different personality after dark. In Fort Myers and Punta Gorda, guided walks introduce travelers to local history, unsettling stories and places associated with reported paranormal activity. Continue south to Key West, and the choices expand to ghost trolleys, haunted walking tours, pub crawls and after-hours encounters with one of the island's most famous residents: Robert the Doll.

These destinations do not need to share one invented legend to make a memorable trip. The connection is the journey itself. Start with a mainland ghost tour in either Fort Myers or Punta Gorda, sail from Fort Myers Beach aboard Key West Express the following morning and spend the next evening exploring the haunted side of Old Town Key West.

Rain in Key West does not have to ruin the day. Tropical showers often come and go quickly, and Old Town is filled with museums, galleries, shops, historic homes and restaurants where you can wait out the weather.

Whether the forecast calls for a passing shower or several wet hours, here are some of the best ways to enjoy Key West when the sunshine takes a break.

What Happens When ParrotHeads Take Over the Beach?

What do you get when you fill a Fort Myers Beach resort with trop rock, loud shirts, raffle baskets, birds with actual feathers and people who can shout “Fins up!” before breakfast?

ParrotPhest, of course.

From October 1 through October 4, 2026, Margaritaville Beach Resort Fort Myers Beach will welcome the flock for four days of music, tropical mischief and very few boring shirts.

And here’s the part ParrotHeads will really appreciate: when ParrotPhest winds down, the original Margaritaville is waiting across the Gulf. Key West Express departs from Fort Myers Beach, making it possible to give this party the Key West encore it deserves.

Just a few steps from the energy of Duval Street, Bahama Village offers visitors a different look at Key West—one shaped by Bahamian heritage, Black history, Caribbean flavors and generations of island life.

This colorful Old Town neighborhood stretches across roughly 16 blocks between Whitehead, Southard, Fort and Louisa streets. Its narrow lanes, historic churches, tropical gardens and pastel wooden homes tell an important part of the Key West story. Although it is easy to explore on foot, Bahama Village deserves more than a quick walk-through. Slow down, look beyond the storefronts and discover the people and traditions that helped make Key West what it is today.

Key West is famous for its sunsets, historic streets, and lively atmosphere, but just beneath the surface lies another world waiting to be explored. Crystal-clear waters, vibrant coral reefs, fascinating shipwrecks, and an incredible diversity of marine life have made the Florida Keys one of North America's premier diving destinations.

Fort Myers Beach is about to get loud—in the best possible way.

ROAR Offshore returns September 11–13, 2026, bringing a weekend of colorful catamarans, flying spray and close racing to the beach. There is even a welcome party on Thursday evening, September 10, for anyone who wants to start the fun a little early.

If you have never watched offshore powerboat racing, imagine a pack of boats charging across the water at more than 90 miles per hour. You hear the engines first. Then the boats burst into view, bounce across the chop and crowd together through the turns. It is fast, noisy and difficult to ignore.

This year's ROAR is different from the event of years past, so forget the old October dates and long list of racing classes. The 2026 weekend has been reimagined around one especially competitive class: APBA Super Stock. The official ROAR Offshore website is the best place to follow announcements as race day approaches.

Things to Do in Key West This Fall

While many travelers wait until winter, locals know that September, October, and November offer warm water, spectacular sunsets, fewer crowds (especially early fall), and some of the island's biggest festivals. Whether you're looking for adventure, fresh seafood, colorful celebrations, or simply relaxing under a palm tree, there's something special happening every month.  Fall truly is one of the best times to visit.

If you're traveling from Southwest Florida, the Key West Express makes getting there easy—letting you skip the long drive and arrive refreshed, ready to explore.

Why Visit Pet-Friendly Key West?

Key West is known for its laid-back island lifestyle—and that relaxed atmosphere extends to pets, too. From outdoor restaurants and waterfront patios to scenic parks and historic streets, there are plenty of places where your four-legged companion is welcome.

Even better, getting there can be part of the adventure.

There's no better place to experience the authentic spirit of Key West than along the Historic Seaport and Key West Bight. While Duval Street is famous for its nightlife and attractions, the waterfront tells the story of the island's rich maritime heritage, vibrant fishing culture, waterfront dining, and unforgettable sunsets.

Everything you need to know about exploring the most famous street in Key West—from iconic attractions and historic landmarks to award-winning restaurants, legendary bars, boutique shopping, and unforgettable island experiences.