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.
Worth pairing with the rest of beach bars down the Keys.
Thirsty for more? Dive into the Bum’s full guide to the best beach bars in Florida.
