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10 Things to Do in Key West When it Rains

10 Things to Do in Key West When it Rains

What’s an island paradise without a little rain? That’s right, the rainy days still happen even in Key West. Rainy season is June thru October but just because we face a rainy day or two, that doesn’t mean the fun has to stop.

Whether you planned your trip before rain showed up in the forecast, or you were hoping to take advantage of fewer crowds and snag sweet deals on a fabulous vacation home during the off-season, there are plenty of things to do in Key West when it rains.

Ready to add some fun back into the forecast? Here are a few of our favorite rainy day activities in Key West!

1. Go to the Movies at the Tropic Cinema

We know this one’s obvious; movies have always been a staple rainy day activity, but in Key West, you’re in for an extra special treat. Complete with an old-timey glittering marquee, statues of Marilyn Monroe, and the smell of buttery popcorn wafting throughout, Tropic Cinema – a non-profit art house – offers a classic movie theater experience.

It’s the perfect rainy-day retreat or evening outing when you want a break from the beach but still crave something quintessentially Key West.

Located just a half block off Duval Street on Eaton, and within walking distance from many major attractions and vacation homes, Tropic Cinema shows films from around the world, including international and independent films, cinematic classics, and big Hollywood blockbusters.

See current showtimes and purchase tickets here.

2.  Explore the Key West Aquarium

When the island skies turn gray, duck into one of Key West’s most fascinating historic attractions — the Key West Aquarium. Originally built in the 1930s as an open-air aquarium, it’s now a charming blend of old Florida history and hands-on marine discovery.

While there are some outdoor exhibits at the Key West Aquarium, there’s still plenty to see inside while you wait out the rain. Inside, you can wander through touch tanks filled with starfish and stingrays, watch feedings of sea turtles and sharks, and learn about coral reef conservation — all while staying dry and comfortably cool.

Get an extraordinary view of local marine life such as tropical fish, sea turtles, and sharks, browse the exhibits, and visit the touch tanks (a favorite if you’re traveling with little ones).

3. Stroll the Key West Butterfly and Nature Conservatory

Another perfect spot to escape the rain, the Key West Butterfly and Nature Conservatory features beautiful indoor gardens, brimming with butterflies, birds, and blooming flowers. And no matter the weather outside, thanks to the unique construction and climate-controlled environment, it’s always a tropical paradise inside the Key West Butterfly and Nature Conservatory!

In addition to the butterfly gardens, you’ll find fascinating insect exhibits and one-of-a-kind art and souvenirs in the gift shop and gallery.

4. Enjoy a Spa Day

The tropical rainstorms that come through Key West can have a calming effect; why not take advantage of this and book a spa day? Imagine melting sore muscles away with a massage or pampering yourself with a pedicure while soothing rain falls, dancing on the tin roofs.

Top-rated spas in Key West include Ocean Wellness Spa, Amri Spa, and Flow Spa — all favored by locals and visitors alike, and within a short distance of your Key West vacation home.

5. Do the Duval Crawl

Most Key West visitors are familiar with the Duval Crawl, a day spent drinking your way through some of the world-renowned bars lining Duval Street. This parade from bar to bar is still a lot of fun when done under umbrellas and raincoats. Some locals even say it’s more fun this way — as the famous song says, “if you like pina coladas and getting caught in the rain.”

Starting on one end of Duval Street and making your way to the other is a favorite challenge for the seasoned Duval crawler. Of course, you’ll want to stop by Sloppy Joe’s Bar, The Green Parrot, Hog’s Breath Saloon, and all the other must-try bars in Key West.

6. Porch Sitting and People Watching — a Key West Tradition!

If you’re renting a vacation rental house or cottage, chances are good you have a front sitting porch to enjoy. The front porch is the perfect place to stay dry while watching the world of Key West go by.

And when you’ve had enough of lounging around the house, you’ll find several establishments downtown that serve wine, beer, or cocktails under outdoor covered porches. A few of our favorites include the Grand Vin Porch on Duval Street for wine sipping, Old Town Tavern and Beer Garden on Duval Street for exotic beers, and Louie’s Backyard on the ocean on Waddell Avenue for a cocktail.

7. Browse Treasures at the Mel Fisher Maritime Museum

The Mel Fisher Maritime Museum in Key West is dedicated to Mel Fisher and his crew’s recovery of sunken treasure ships — most renowned for the recovery of the Nuestra Señora de Atocha, a Spanish treasure galleon that sank in 1622 while passing through the Florida Straits.

This museum is the perfect place to spend a few hours enthralled by historical tidbits and sunken treasures. There’s also a gift shop and jewelry store where you’ll find unique, one-of-a-kind pieces.

And if you’re looking for more Key West museum fun, the island is also home to:

  • Ernest Hemingway Home and Museum
  • Truman Little White House
  • Key West Lighthouse and Museum

8. Take An Old Town Trolley Tour — Yes, Even in the Rain!

Riding the Old Town Trolley in the rain is a Key West Tradition. Under the protection of the trolley’s roof, you can still have a good look around Key West, no matter the weather. It’s one of the island’s most popular tours, even on a gloomy rainy day.

The Trolley also offers hop-on, hop-off service, with stops around all the island’s most popular attractions. The dry ride makes this an excellent way to get around while exploring in the rain.

9. Go Rum Tasting

Key West and rum go hand in hand, so it’s no wonder that rum tastings are a favorite among rainy-day activities in Key West!

Get a behind-the-scenes look at what goes into making one of the island’s most famous spirits, and of course, taste different varieties of rum at Papa’s Pilar, inspired by Mr. Hemingway himself, or Key West Legal Rum & Distillery, where you can learn to mix up some killer mojitos.

10. Eat Good Food!

We know, like anyone ever needed an excuse to dine out in Key West! But it bears repeating, the island has no shortage of amazing restaurants. From casual seafood and Caribbean-inspired cafes to fine dining establishments serving up steak and lobster, there’s something for everyone in Key West.

With wet weather making outdoor dining difficult, we suggest sitting down at one of these rain-friendly restaurants:

  • Marquesa Key West
  • Duffy’s Steak and Lobster House
  • 7Fish Key West
  • Santiago’s Bodega

And for dessert — nothing beats Better Than Sex Dessert Restaurant (pun intended!) or stop by one of the many sweet shops serving up signature treats like Key lime pie, homemade fudge, and ice cream, and more.

Explore Key West Rain or Shine!

While we’ve only scratched the surface of all the Key West indoor activities that are perfect for a rainy day, rest assured, by the time you get through half of these, the rain will have likely passed.

Of course, when staying with VHKW, you can always enjoy a rainy day, cuddled up on the couch, watching movies in your own private, comfortable vacation rental. And if you need more suggestions or help booking activities or transportation, you’ll have access to our renowned concierge service to assist.

Even with the dreary weather, Key West will still steal your heart. We’ll leave you with our favorite quote for a rainy day in Key West: “And you’ll always love me, won’t you? Yes. And the rain won’t make any difference? No” – Ernest Hemingway

October 23, 2025