Nightlife in the Upper Keys tends to start before the sun goes down, often at noon, as most people -- visitors and locals alike -- are on vacation. Also, many anglers and sports-minded folk go to bed early.
Hog Heaven, MM 85.3, just off the main road on the ocean side, Islamorada (tel. 305/664-9669), opened in the early 1990s, the joint venture of young locals tired of tourist traps. This whitewashed biker bar is a welcome respite from the neon-colored cocktail circuit. It has a waterside view and diversions such as big-screen TVs and video games. The food isn't bad, either. The atmosphere is cliquish because most patrons are regulars, so start up a game of pool to break the ice. Open daily from 11am to 4am.
No trip to the Keys is complete without a stop at the Tiki Bar at the Holiday Isle Resort, U.S. 1 at MM 84, Islamorada (tel. 305/664-2321). Hundreds of revelers visit this ocean-side spot for drinks and dancing at any time of day, but the live rock starts at 8:30pm. The thatched-roof Tiki Bar draws a mix of thirsty people, all in pursuit of a good time. In the afternoon and early evening (when everyone is either sunburned, drunk, or just happy to be dancing to live reggae), head for Kokomo's, next door. It often closes at 7:30pm on weekends (5:30pm on weekdays), so arrive early. For information, call the Holiday Isle Resort. Rumor has it that greedy developers are going to raze the Tiki Bar to make way for million-dollar condos, but loyal boozehounds are raising hell over it, and some are even trying to have the Tiki Bar declared a Florida landmark! Stay tuned.
Locals and tourists mingle at the outdoor cabana bar at Lorelei. Most evenings after 5pm, you'll find local bands playing on a thatched-roof stage -- mainly rock or reggae, and sometimes blues.
Woody's Saloon and Restaurant, U.S. 1 at MM 82, Islamorada (tel. 305/664-4335), is a lively, wacky, loud, raunchy, local legend of a place serving up mediocre pizzas, buck-naked strippers, and live bands almost every night. The house band, Big Dick and the Extenders, showcases a 300-pound Native American who does a lewd, rude, and crude routine of politically incorrect jokes and songs starting at 9pm Tuesday through Sunday. He is a legend. By the way, don't think you're lucky if you're offered the front table: It's the target seat for Big Dick's haranguing. Avoid the lame karaoke performance on Sunday and Monday evenings. There's a small cover on most nights. Drink specials, contests, and the legendary Big Dick keep this place packed until 4am almost every night. Note: This place is not for the faint of heart, but more for those from the Howard Stern school of nightlife.
For a more subdued atmosphere, try the handsome stained-glass and mahogany-wood bar and club at Zane Grey's, on the second floor of World Wide Sportsman, MM 81.5 (tel. 305/664-4244). Outside, enjoy a view of the calm waters of the bay; inside, soak up the history of real longtime anglers. It's open from 11am to at least 11pm (later on weekends). Call to find out who's playing on Friday and Saturday nights, when there's live entertainment and no cover.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.