Perhaps the most impressive feature of Schooner Wharf is that it retains its local favorite status in spite of a proximity to tourist-overrun Conch Republic next door. Maybe it’s the gravel floor and plastic patio furniture that keeps the spring breaker crowd at bay, but us and a legion of loyal locals are glad to enjoy Schooner Wharf’s perfect situation in the harbor, live music, and two happy hours a day without having to worry about too much of a crowd. But make no mistake, the Wharf gets jumping rowdy in the later hours of the evening. All in all, this is one of our favorites in Key West. Don’t miss Frank’s Magic Bar, where famous magician Frank (well, kinda, his dad was the magician on the Bozo show) runs a grape vodka-fueled, Copperfield-caliber performance that never gets old. If you’re lucky, you just may catch the Schooner Wharf Regatta, a booze-addled boat race between locals who have cobbled together skiffs out of junk they had lying around. If you do if you miss the Regatta, just look to the ceiling of the Schooner Wharf structure to see some of the better boats from previous races suspended from the roof. Anyways, enjoy a Corona on the marina if you are going to be by the Wharf.
Also, if you are on the island the first week of May, don’t miss the Cinco de Mayo celebration. There’s a sombrero competition, hot pepper eating competition, and a taco eating competition: 3 spicy tacos, a Corona, a fresh jalapeno, and a shot of tequila. James won in 2014 (see below) after 82 seconds.