Tucked under the Jewfish Creek Bridge at the northern gateway to the Keys, Gilbert’s Tiki Bar is the first real taste of island life for anyone heading south on US-1, and plenty of people stop here and never make it any further. A sprawling waterfront resort complex with a big palm-roofed tiki bar, this boater’s favorite draws everything from inflatable dinghies to multi-million dollar yachts to its generous dockage. The bar staff have been here for years, the views and sunsets are spectacular, and the live music pulls a nonstop crowd on weekends. Order a frozen drink, find a seat with a water view, and let the Keys officially begin.
Thirsty for more? Dive into the Bum’s full guide to the best beach bars in Florida.
