This laid-back dive bar is a big draw for gay travelers. Here you'll find a friendly atmosphere, and it's a great place to meet some locals. There are regular karaoke sessions which can drag on into the early hours. Bobby's Monkey Bar has the best Happy Hour in Key West, offering domestic alcohol for only $3 every day after 8 pm. Bobby's has been compared to Cheers - but imagine if the cast of Cheers were gay! You can't get food here, and it's a bit off the beaten track, but still very much worth a visit.