If you need a chill night relaxing under the stars or don’t want to spend a ton of cash, there are a few spots offering free movie nights. (If I find more I will update.)
Outdoor movies under the palm trees followed by a night sleeping on a sailboat doesn’t sound too shabby.
24 North Hotel: (New Town)
I’m a big fan of this hotel. For one, the Cuban refugee chug that we rescued is sitting by the pool area. Second, they never kick me out when I sit and use their free WiFi all day, and now they are becoming the new “it” place to hang out for Stock Island and New Town – thanks to a new green lawn/movie zone between the 24 North’s pool and the Gates Hotel. Plus, the Blind Pig food truck is there. So far, I’ve had the chicken wrap (great) and the blind pig signature (which was not as good).
For the movies, they roll out a little portable bar and popcorn booth (and liquor bar) on the lawn and I’ve heard that they are debuting a new craft beer bar soon. This hotel is about a 25-minute walk to the kayaks – not bad if you like taking late night strolls. Movie-wise, they’ve done the Breakfast Club, Pretty Woman, and other classics. Check out the events calendar here: https://www.facebook.com/pg/24NorthHotel/events
The Marker (Historic Seaport)
This place also has free movies by the pool and is located downtown in the Historic Seaport. In the past they’ve done Bridesmaids, Elf, and Dumb and Dumber, but the schedule is pretty random. It’s right near our favorite bar, Schooner Wharf. https://www.facebook.com/pg/TheMarkerResort/events/.
Bayview Park: (Old Town)
On Fridays – but not every Friday (every first and third), Bayview Park hosts a movie night geared toward families (the Nut Job 2 and Annie are up on the roster). Side note: on Thursdays, this park also has a farm market.
Not Free but Also Cool:
Key West Film Festival (November):https://kwfilmfest.com/
Tropic Cinema: (Really Awesome little theater): https://www.tropiccinema.com/