One of the reasons so many people visit Key West each year is the island’s casual, quirky atmosphere. And the best way to absorb that atmosphere is to forget you’re a visitor.
Instead, adjust your mindset. Stop thinking of yourself as a “tourist” and instead self-identify as “temporary local.”
Why? Because if you adopt the “tourist” mindset, you’re all too likely to limit your experience to typical “tourist” activities. But if you think of yourself as a local — even if it’s only for a few days — you’re more likely to search out and embrace off-the-beaten-path pursuits that longtime residents enjoy.
For example, here are five pastimes that the average visitor might not find out about or choose to spend time and energy experiencing. But trust me … they’re genuinely rewarding if you want an out-of-the-ordinary vacation that creates lasting memories.
1. Bike or stroll through Key West’s Old Town neighborhood, the largest predominantly wooden historic district in the entire United States, as evening falls. It’s a simple activity, but a very worthwhile one. Allow yourself to get lost and simply wander, discovering lovingly restored Victorian homes and cottages along narrow lanes, while enjoying the fragrance of luscious flowers drifting from behind white picket fences.
2. Try smoked fish dip at the Hogfish Bar & Grill, a hard-to-find hideaway on Stock Island just off Key West, sitting outdoors at a weathered picnic table. The smoked fish dip combines a creamy texture with a satisfyingly hearty taste, and the picnic tables overlook picturesque vessels moored along the dock — everything from houseboats decorated with exuberant island art to a schooner with a fascinating history.
3. If you’re looking for a Key West locals’ hangout with great live music, stop by the Schooner Wharf Bar. Standing on the waterfront in the Historic Seaport, it’s the kind of funky open-air place where you can bring your dog, your girlfriend and half a dozen fishing buddies — and everyone will have fun. Try to get there in time to hear eccentric troubadour Michael McCloud, who plays most afternoons. His tales, and his songs, are spiced with irreverent humor.
4. Immerse yourself in creativity during neighborhood art strolls held monthly in Key West. One of the best is staged on Upper Duval Street on first Friday of each month, while another (held on the third Thursday of each month) features White Street and a portion of Truman Avenue. At both you can find unique visual art, meet the Florida Keys artisans who create it, and explore intriguing galleries alongside residents who are passionate about the island’s lively cultural community.
5. Head to Fort Zachary Taylor Historic State Park for a tranquil afternoon swimming and lazing beside the Atlantic Ocean. “Fort Zach,” as the park is affectionately nicknamed, is renowned for its shady picnic area cooled by ever-present breezes — and its 1,000-foot beach that Key Westers regard as the island’s best. Spend some time snorkeling in the relatively deep near-shore waters, spotting colorful tropical fish around rocky promontories, or explore the weathered Civil War–era fort that gave the park its name.
Every year, countless visitors flock to Key West for a vacation escape from the stresses of the “real world.” When it’s your turn to travel, do it the right way — by adopting the “temporary local” outlook, enjoying away-from-the-mainstream offerings, and embracing the easygoing vibe that makes the island so appealing.