The Conch Connection

Fort Zachary Taylor is one of those Key West places that can surprise you twice. First, there is the setting: a massive brick fort tucked beside one of the island’s favorite beaches. Then there is the history. Behind those shaded archways and weathered walls is a story of military strategy, Union-held Key West and cannons that spent decades buried inside the fort itself.

Today, “Fort Zach” is an easy place to mix a little time travel with a relaxed afternoon by the water. You can wander through old gun rooms, stand beside historic artillery and then trade the brick corridors for snorkeling, swimming or a picnic beneath the trees. That combination makes it much more than a stop for dedicated history buffs.

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.

Key West Race Week Has a Sound All Its Own

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.

This 10 day mostly, free event features the unique opportunity to experience the voices, back stories, and personalities of some of the most influential and internationally-recognized singer-songwriters at some of the most famous venues across Captiva, Sanibel, Historic Downtown Fort Myers and Fort Myers Beach! And include some of the biggest names around: Brian Sutherland, Locash, Edwin McCain and about 50 more!

October 16-25, 2026

What Is Key West Fantasy Fest?

Every October, Key West transforms into one of the most exciting destinations in Florida during Fantasy Fest. This annual 10-day celebration is famous for its elaborate costumes, lively parades, themed parties, live entertainment and unmistakable island spirit.