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.

Here we go, aging ourselves a little.

How long does it take to get to Key West from Southwest Florida? Aboard Key West Express, the trip from Fort Myers Beach takes approximately 3.5 hours from port to port.

Driving from Fort Myers takes a little over five hours without lengthy stops—and that does not include traffic delays, rest breaks or finding parking after you arrive.

With Key West Express, those hours are spent relaxing across the Gulf instead of watching the highway. You can enjoy the onboard amenities, take in the views and arrive within easy reach of Old Town.

Key West and Cuba are separated by roughly 90 miles of water, but their shared story has been unfolding for generations. Cuban immigrants helped build the island's economy, supported the struggle for Cuban independence and left a lasting mark on local politics, education, art, architecture, language and food.

That heritage is not confined to a museum display. You can experience it in a strong cup of café cubano, a historic building on Duval Street, a plate of roast pork and plantains, or the Spanish name many locals still use for Key West: Cayo Hueso. Arriving aboard Key West Express places you near the Old Town streets where much of this history unfolded.

Have you ever wanted to run with the bulls?

How about doing it without an actual bull chasing you?

Welcome to Hemingway Days, where Key West puts its own wonderfully unconventional spin on one of Ernest Hemingway's favorite Spanish traditions.

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.