Key West has a habit of doing food its own way.
You’ll find lobster rolls served from tiny storefronts, wildly creative tacos coming out of a food truck and fresh seafood that tastes even better when you’re wearing flip-flops. A few of these colorful local spots have even caught the attention of Diners, Drive-Ins and Dives.
Three Key West-area restaurants received the national spotlight. Two are still serving hungry island visitors today: DJ’s Clam Shack and Garbo’s Grill.
St. Patrick's Day feels different in Southwest Florida. Instead of piling on winter layers, revelers reach for sunscreen, green shirts and a spot near the music. Fort Myers brings the Irish-pub energy, Naples fills downtown with a long-running parade, and Key West adds the kind of tropical personality that can turn a traditional holiday into an island getaway.
For travelers ready to carry the celebration across the Gulf, Key West Express connects Fort Myers Beach with Key West—giving the holiday a decidedly Floridian twist before you ever reach Duval Street.
What does Thomas Edison, mid-February and a 2 week party all have in common? The Edison Festival of Light, of course. Each February the City of Ft Myers recognizes its most famous winter resident, Thomas Alva Edison. He built a sprawling home and laboratory along McGregor Boulevard in 1885. Over the years he also encouraged a number of his friends to make the move south. Henry Ford was his most famous friend who shared the property on McGregor Boulevard known as the Edison Ford Estate.
There are plenty of places to watch a ball drop. Key West, naturally, has a few more colorful ideas. On Thursday, December 31, 2026, you can ease into the evening with a famous sunset, then ring in the new year with a giant red shoe, a glowing conch shell or a pirate wench descending from a schooner mast—all within a short Old Town walk of one another.
That wonderfully odd mix is exactly why New Year's Eve here is so much fun. The air is warm, the streets are lively and a simple midnight countdown turns into a story you will be telling long after you have traded flip-flops for winter boots. The island's current New Year's Eve event guide confirms the big three celebrations, but individual venue details can change, so check the official pages before you head out.
Five days. Five continents. A collection of chefs, winemakers, artists and unforgettable Key West settings.
The Key West Food & Wine Festival returns January 27–31, 2027, with intimate dinners, wine experiences, tastings and special events held at locations across the island. Now celebrating its 18th edition, the festival turns Key West into a culinary journey where the setting is just as memorable as what is poured and served.
The 2027 theme, “Connected by the Oceans,” explores how water has carried ingredients, cooking traditions, wine culture and human stories between continents. It is an especially fitting idea for Key West, an island shaped by the Atlantic Ocean, the Gulf and generations of cultural exchange.
If you are thinking about attending, this guide covers the dates, theme, announced events, venues, ticket information and practical tips for planning a delicious winter getaway.
Celebrate your romance with Seashells, Sunshine & Sand. Some people dream of this day forever and should be one of the most memorable moments of your life. Whether your dream wedding includes
glistening tropical waters with sand between your toes, sophisticated sunset elegance at a five-star resort or anything in between, America's Caribbean Island Paradise offering year round weather, breathtaking water views and an abundant array of options will make your special day exactly as you imagine. Make memories at Smather’s beach, Higg’s beach, Fort Zachary Taylor historic state park or the gazebo overlooking the Atlantic Ocean at West Martello Tower & Gardens.
Photo Credit: HemingwayHomeEvents via Instagram by @irismoorephoto
You can even forgo the traditional wedding and broadcast your nuptials digitally, as some have taken to social media to live-stream their wedding, for those that are far and away and could not attend personally. Not only can you invite and and everyone, you want, but you'll also have virtual remembrance as well.
Fort Myers Beach is about to become one very serious sandbox. The 36th Annual American Sand Sculpting Championship returns November 19–23, 2026, bringing five days of towering sculptures, live competition and hands-on fun to the beach behind DiamondHead Beach Resort.
First comes the rumble. Then the spray, the bright race boats and the kind of crowd that knows something very loud and very fast is about to happen. Key West Offshore World Championship Week turns the island into a playground for offshore-racing fans, curious first-timers and anyone who enjoys a little extra buzz with their sunshine.
From November 1–8, 2026, the championship brings world-class teams, waterfront viewing and plenty of reasons to linger after the engines quiet down. You do not need to know the difference between a catamaran and a V-bottom to have a great time. Just bring your sunglasses, a little patience for a lively island and a healthy respect for horsepower.
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.
