Key West, Florida

This quirky, LGBT-friendly town is known for Ernest Hemingway's home and its six-toed cats, sunset celebrations, and Duval Street's many bars, restaurants, and nightclubs.

It's also known for pricey hotels. Seek out NYAH (Not Your Average Hotel) for rooms that take up to six guests — without added fees. Off season, rates can be as low as $174 for four beds.