Key West looks easy. The island is compact, the drinks are cold and almost every street seems to lead toward water, music or food. Then you arrive with a schedule packed tighter than a carry-on bag, discover that “just down the street” feels different under the tropical sun and realize your must-do list has somehow become a must-hurry list.
Scott Schofield
Recent Posts
Winter may mean snow, ice and heavy coats across much of the country. In Key West, it means sunshine, swimsuits, waterfront dining, outdoor adventures and some of the island's most popular events.
December, January and February bring comfortable temperatures and plenty of reasons to spend the day outside. You can explore Old Town, head to the beach, listen to live music, tour historic homes or simply find a waterfront table and remember that somewhere else, someone is shoveling a driveway.
If you're traveling from Southwest Florida, Key West Express makes getting there part of the getaway. Relax on the ride across the Gulf and arrive in Key West near the Historic Seaport, ready to explore.
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 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.
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.
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.
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.
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 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.
