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.

Key West, a vibrant island paradise known for its laid-back atmosphere and stunning sunsets, also boasts a thriving art scene that captivates visitors and locals alike. With its unique blend of Caribbean culture and artistic expression, Key West offers a diverse range of art forms, from traditional painting and sculpture to contemporary installations and performance art.

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.

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.

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.

Every January, Key West trades a little of its tropical calm for guitars, songwriters and the unmistakable sound of Red Dirt and Americana music. Mile 0 Fest turns the island into a five-day music vacation, with major evening performances at the waterfront amphitheater and smaller shows unfolding at beaches, resorts, theaters, bars and other venues around Old Town.

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.

Planning a family vacation that everyone will enjoy can be a challenge, but Key West makes it surprisingly easy. From fascinating marine life and historic landmarks to beautiful beaches, interactive museums, and unforgettable sunsets, there's something here for every age. Whether you're visiting for a single day or an extended stay, you'll find plenty of family-friendly activities that create lasting memories.