Key West, Florida

Key West is the southernmost point of the continental United States and one of the most unique lifestyle travel destinations in North America. This small island city at the end of the Florida Keys has a long history of welcoming free spirits, artists, writers, and those seeking an alternative way of life. Key West's relaxed, anything-goes atmosphere, beautiful turquoise waters, vibrant Duval Street nightlife, and strong LGBTQ+ community make it a natural destination for lifestyle travellers. The island's small size makes it very walkable, and its laid-back culture encourages connection and openness. Key West is particularly popular for Fantasy Fest, an annual ten-day festival in October that celebrates creativity, body art, and freedom of expression.