The Florida Keys generally see mild weather, sunshine, and very little rain – but it does happen. Be aware that summer in the tropics is the rainy season, and as a general rule of thumb you can expect a serious afternoon shower almost every day for an hour or so. One of the main ways to occupy your time when this happens is to head to the bars – but let’s face it, there are some places that travelers wouldn’t mind being stuck in, and other watering holes that lose their luster fairly quickly. Here are my favorite places on the island to waste away a few hours while it’s raining (or when it’s not).
Schooner Wharf Bar: A Key West Classic — Photo courtesy of Schooner Wharf Bar
Let’s start with the classics: Schooner Wharf is as authentic as Key West can get, and is one of the last remaining holdouts that has not yet caved in to the modern age. The bathrooms are technically outdoors, the wood floor is polished from foot traffic alone, and no one seems to mind if you made yourself look like a fool the night before. This waterfront restaurant is also an ideal place to grab a bite; breakfast, lunch, or dinner. Try the fresh mahi mahi or snapper melt with a house mango sauce topped with sautéed onions and mushrooms.
The Green Parrot might be the best place to escape the rain at nighttime because of its music scene is all over the map. One night may be a Cuban jam session; the next is Gypsy Jazz, followed by a meeting of The Green Parrot Ukulele Association. The Parrot has seen little in the way of re-modeling in say, 100 years or so, it still serves semi-stale popcorn, and there's a strange jellyfish-like parachute hanging over the top of the bar.
The Music at the Green Parrot — Photo courtesy of Amber Nolan
Visitors to the Rum Bar, a perennial favorite on Duval Street next to the Speakeasy Inn, will leave with a bit more knowledge about the Caribbean’s favorite liquor. Visit with "Bahama Bob" the mixologist that is well versed in the art of bartending. While the staff at the fraternity-style pubs on Duval toss together a Jack and Coke, Bahama Bob will make you a "Pain Killer," or a pina colada made from scratch (with fresh nutmeg), and mojitos made with mint and fresh lime juice.
Shots and Giggles is one of Key West newbies, but the mini-bar approach allows visitors to easily make friends if they end up stuck in the storm alone. With just six bar stools and some common areas that resemble a living room, fruit infused shots, and flat screen TVs, the sun may reappear hours before patrons of the bar even realize it. 
Two Cents: the New Gastropub — Photo courtesy of Two Cents
Wine bars have been sprouting up like weeds around Key West, but they are a welcome change of pace. Chris Schultz is leading this charge with the opening of The Porch wine bar and 2 Cents, the new gastro pub that invites visitors to sit, linger, chat, and enjoy the endless free bacon. Set in the historic, haunted Porter House, things could get a bit eerie at The Porch during a thunderstorm - especially after a couple glasses of wine and some ghost stories. If you’re lucky you might be able to catch the occasional movie showing.
As the saying goes, the best thing to do when it’s raining is just let it rain.