The Conch Connection

Planning the perfect family vacation means finding a destination that offers something for everyone. From exciting outdoor adventures and fascinating history to beautiful beaches and unforgettable sunsets, Key West checks every box.

Whether you're traveling with toddlers, teenagers, grandparents, or the whole extended family, the island offers experiences that bring generations together. Better yet, if you're traveling from Southwest Florida, the vacation begins the moment you board the Key West Express, where the journey is just as memorable as the destination.

If you're searching for the best day trip from Fort Myers Beach, you're spoiled for choice. Southwest Florida offers beautiful beaches, nature preserves, and waterfront towns, but one destination delivers an experience unlike any other—Key West.

 Located at the end of the Florida Keys, Key West offers a tropical island experience that's surprisingly easy to reach aboard the Key West Express from Fort Myers Beach.  Colorful streets, historic landmarks, tropical scenery, fresh seafood, and a laid-back island atmosphere make it one of Florida's most unforgettable destinations. Better yet, you don't have to spend the day driving to get there.

Year round weather makes Key West an ideal vacation spot for outdoor adventure enthusiasts and adrenaline junkies alike. This special little island offers an abundance of opportunities for every indulgence and thrill seeker. Planning ahead allows you to get the most out of your Key West excursion. For your convenience, we have included a selection of details on a variety of heart pumping activities.

Grab the kids and getaway!

Here in Florida, anytime is the time to plan a vacation.  Key West is the ideal getaway filled with activities and adventure to make smiles and memories for any and everyone!

Annual Key West BrewFest

September 4 - 6, 2026

The past Key West BrewFest events have been so much fun and an amazing success for the local charities, the committee is teaming up to bring it to you again! Between 150 and 200 beers and micro-brews are on tap at this "tasty" annual event that benefits the charitable efforts of the Key West Sunrise Rotary Club of the Conch Republic.

Like snowflakes, no two sunsets are ever alike. There is no shortage of places around the world to watch our favorite star sink beyond the horizon, igniting the sky with radiant hues that cast magic over the surrounding scenery. However, whether you are overlooking the ocean from beach, pier or boat….Florida offers some of the most spectacular places to view the vibrant range of colors that infuse the sky and shimmering sea – perhaps with a green flash, if you’re lucky.

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.

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.

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.

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.