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.

Key West may be famous for colorful sunsets, historic streets and laid-back island energy, but some of its most unforgettable residents live beneath the water.

Key West Extreme Adventures offers visitors an opportunity to leave the shoreline behind and journey into the backcountry waters surrounding the island. Its shark and wildlife eco-tour combines close encounters, local knowledge and family-friendly excitement aboard the custom-built Tiger Cat.

For travelers hoping to discover a wilder side of Key West, this is one adventure that deserves a place on the itinerary.

Few experiences reveal the natural beauty of Key West quite like a nighttime kayaking adventure. As the sun sets and the crowds drift away from Duval Street, the island's waters transform into a peaceful world filled with stars, wildlife, glowing marine life, and the gentle sounds of the Florida Keys.

There’s no better way to experience Key West than by exploring it on foot. From colorful historic homes and legendary landmarks to lively waterfronts and tropical side streets, a walking tour allows visitors to fully experience the charm and personality of the island at their own pace.

Some Florida adventures begin where the pavement ends. Everglades City is one of them.

This small fishing town sits beside a seemingly endless puzzle of mangrove islands, twisting creeks and open bays. Step aboard a boat and the town quickly disappears behind you. Pelicans skim the water, dolphins may surface beside the wake and every narrow channel looks like it might lead somewhere completely new.

Everglades City and the Ten Thousand Islands are a natural addition to a Southwest Florida road trip—especially when the next chapter includes a Key West Express crossing from Fort Myers Beach. Give this wild corner of Florida its own day, and it may become one of the stories you tell most often after the trip.

Key West does not slow down when the sun disappears. The island simply changes moods. Sunset crowds gather along the waterfront, live music spills onto Old Town streets, historic buildings become the setting for ghost stories, and illuminated kayaks glide through dark mangrove creeks.

The best things to do in Key West at night include the Mallory Square Sunset Celebration, sunset cruises, live music on Duval Street, drag shows, ghost tours, night kayaking, waterfront dining, theater performances and relaxed walks through Old Town. Most evening attractions are concentrated around Mallory Square, Duval Street and the Historic Seaport, making it easy to combine several experiences in one night.

Key West Has Always Been Happily a Little Different

Key West does not do ordinary especially well. This is an island where a cemetery comes with a self-guided map, a legendary bar has a tree growing through the middle of it, and a day on the water can end with you climbing, sliding and trying not to splash off a floating playground.

That is part of the charm. The usual beaches, boats and sunset views are still here, but leave a little room in your plans for the stranger side of the island. These five experiences are a good place to start.

Key West, Florida.... There is so much to see and do on this island oasis, the Southernmost Point of the United States. What to choose?  How to decide?  S.O.S! We're here to give you a hand with just a few of the best things to make the most out of your 2 day vacation.

Key West may be famous for sunsets, tropical drinks and turquoise water, but look beyond the island atmosphere and you'll discover one of Florida's most fascinating historical destinations.

For more than two centuries, Key West has been shaped by sailors, wreckers, soldiers, cigar makers, presidents, writers, artists and immigrants from Cuba, the Bahamas and beyond. Its strategic location between the Atlantic, the Gulf and the Caribbean helped turn a small island into a surprisingly important center of maritime trade, military defense and cultural exchange.

Better yet, much of that history is concentrated within Old Town. Arrive aboard Key West Express, and you'll step ashore within easy reach of museums, historic homes and neighborhoods where those stories actually unfolded.

If history is your reason for exploring, here are some of the places—and stories—you won't want to miss.

Discover the Secrets of Historic Key West

Key West is known for its beautiful sunsets, colorful architecture and laid-back island lifestyle, but beneath its tropical charm lies a fascinating history that spans centuries. From Native American settlements and Spanish explorers to literary legends, presidents and treasure hunters, the island has countless stories waiting to be discovered.