DIVE-IN THEATRE AT THE PEARL
Outdoor films aren't necessarily rare in San Diego, thanks to the fact that our weather is the stuff of nationwide envy. But unless you have your own projector and large canvas screen in your backyard, there's only one place you can watch movies from the comfort of a swimming pool, with a cocktail in your hand. Every Wednesday night, the Pearl Hotel in Point Loma features its Dive-In Theatre, screening a slice of the (usually '80s or '90s) pop-culture canon—from Beetlejuice to The Big Lebowski—poolside with a drink and, if you're feeling peckish, dinner (The Best Burger and Fries lives up to its name).
Reservations are accepted at The Pearl for those who want to secure a front row seat (those seated in the front will likely not get wet, in case you're wary of the possibility), and it's first-come first-serve for those without reservations. However, use of the pool is free only for guests. It'll cost you the price of a drink if you're not staying the night, though it's a pretty good deal, all things considered. That rule may or may not be in place to keep freeloading frat boys from ruining it for everyone else, but whatever the case, libations poolside with the Coen Brothers and some crispy shoestring fries isn't a bad way to spend a Wednesday evening.
CINEMA UNDER THE STARS
During the summertime, there are numerous opportunities to see movies in outdoor settings, thanks to the warm summer nights that, truthfully, aren't unique to just summer in San Diego. Balboa Park has outdoor screenings, Stone Brewing in Liberty Station hosts outdoor screenings, and the La Jolla Athenaeum hosts Flicks on Bricks. Yet there's only one dedicated outdoor movie theater in the city of San Diego, Cinema Under the Stars, and it operates year round. So if it's a winter screening that you're in the mood for, there's a venue for you to take advantage.
Tucked behind a humble entrance on Goldfinch Street in Mission Hills, Cinema Under the Stars is a proper theater with seating provided in comfortable, reclining chairs. Its lineup of films is exclusively composed of cinematic classics, whether it's Hitchcock, Breakfast at Tiffany's or Raiders of the Lost Ark. As with any theater worth its salted popcorn, Cinema Under the Stars has concessions, which can come in handy during winter months when you might need a cup of coffee or hot chocolate to keep you toasty. Don't forget to bring a blanket.
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