by Captain Hook's | May 20, 2026 | Things to Do
Ask any Key West local when to visit and a lot of them will tell you May. Spring break crowds are gone, summer heat hasn’t fully settled in, hotel rates drop, and the water is warm enough to stay in all afternoon. It’s a month that doesn’t get nearly...
by Captain Hook's | Dec 2, 2025 | Things to Do
December in Key West marks the shift from hurricane season to our peak dry season. It’s the time of year when “winter” means sunny days in the 70s and the humidity finally breaks. The island leans into a tropical holiday aesthetic: you’ll find palm trees...
by Captain Hook's | Aug 28, 2025 | Things to Do
September might sound like an in-between month. A pause after the summer rush and before the winter crowds hit, but Key West in September is often one of the most rewarding times to visit. You’ll find a lively calendar packed with unique festivals, fewer lines at top...
