Chart Room Cocktail Lounge

"This alleged site of Jimmy Buffett’s first Key West gig is located deep inside a hotel (but open to the public). Every inch of the small room is covered in a flag, photo, or bumper sticker, and there are complimentary peanuts and hot dogs for anyone brave enough to reach into the slow cooker." - ryan pfeffer, mariana trabanino, virginia otazo

"A legendary bar that started as just a simple hotel room decades ago inside Pier House Resort & Spa. It’s a small space, but the cold drinks and free bar snacks have been a draw for locals and tourists for years. In the 1970s, a young Jimmy Buffet would play here regularly in exchange for free drinks while he workshopped songs that would later become some of his biggest hits." - Amber Love Bond

"Key West bars, especially the popular ones, can get crowded. So if you’re looking for somewhere to escape—and if you generally prefer drinking at a dive bar—go seek shelter at Chart Room. This Key West staple is impossible to stumble upon unless you know about it, as it’s located inside a bougie resort, but completely open to the public. Every inch of the small room is covered in a flag, photo, or bumper sticker, and it’s quiet enough for a conversation or a game of backgammon over a very tasty Old Fashioned. Also, there are complimentary peanuts and hot dogs for anyone brave enough to reach into the slow cooker." - ryan pfeffer