Tavern 'N Town
841 North Roosevelt Boulevard
Located in the Marriott Beachside Hotel on N. Roosevelt Blvd. near Stock Island, if you're staying in Old Town, it's probably best to bike or cab to Tavern 'N Town; a cool, upscale, cosmopolitan space that is different from most of what you'll find elsewhere in Key West, and hence it's popularity with the locals. My favorite Tavern 'N Town activity is the live jazz happy hour on weekdays.