Best Rainy Day Activities in Key West, Florida (Indoor Activities)

Published: 3/24/24

What To Do in Key West When It Rains

If it’s currently raining in Key West or you’re seeing storm clouds in the forecast for your Florida Keys vacation, there’s no need to despair.

Contrary to popular belief, it isn’t always sunny in Key West, Florida. I personally spent a rather rainy week in Florida‘s southernmost town in early December 2023. But despite the rainy, cool weather, we found more than enough fun things to do during our grey Florida Keys days. 

There’s no reason to call it a zero day when it rains in Key West. With dozens of museums, classes, family activities, house tours, and other indoor activities, once you get started exploring some of these Key West hidden gems, you might find yourself wishing for more inclement weather!

Read on for a round up of the island’s best indoor activities and discover how to have a perfect day in Key West even when it rains.

1) Hemingway Home

The number one attraction in Key West, the Hemingway Home deserves a visit regardless of the weather. Home to the famous American writer for approximately 10 years starting in 1931, the Hemingway Home today celebrates Hemingway through exhibits and a carefully reconstructed writing studio.

Even if you couldn’t care less about Hemingway, the house is a beautiful example of Key West architecture.

The biggest draw for many are the dozens of cats who lived on the Hemingway Home grounds. When we visited there were 61 (!) cats living on the 1.5 acre estate. Many of these furry friends descended from the Hemingway family cat, Snow White, and like Snow White, they have six toes.

While it’s a little harder to enjoy the gardens during a rain shower, you do get the unique experience of watching the kitties lap up rainwater off the tiled pool deck.

(And yes, I did stalk Ernest Hemingway around the globe in late 2023. I also found a Hemingway inspired bar in Lake Como during my trip to Milan.)

2) Truman Little White House

Did you know that President Truman used to escape to Key West during his presidency?

Back in the day, the northwest corner of the island was a U.S. Naval Base. The Keys’ shallow waters prevented this base from having any real strategic use, but since the U.S. government retained ownership of the land, it became an important presidential retreat spot. Today, it’s known as Truman Little White House.

If you’re interested in American history, you’ll love the hour-long tour of this unique presidential retreat. (Spoiler: Truman wasn’t the only notable house guest to stay here!)

Otherwise, just come for an interesting glimpse into 1950s living. If you’re an elderly millennial like me, it might remind you of your grandparents’ house.

Admission is a little pricey, but you can bundle it with a couple other good Key West rainy day activities: the Old Town Trolley and Shipwreck Museum.

3) Key West Pie Crawl

I think every day’s a great day for a slice of key lime pie, but it tastes especially refreshing on a rainy day. If the rain’s not letting up any time soon, why not set out in search of your favorite slice of key lime pie in Key West.

I recommend starting at the Key West Key Lime Pie Company or Old Town Bakery and working your way down Duval Street past Kermit’s and Limes and Pies. Moondog Café, with its cozy indoor seating, makes a great place to wrap up your “pie crawl.”

4) Watch a movie

You can’t beat a movie on a rainy day. For an “only in Key West experience”, head to the Tropic Cinema. This independent, retro-style movie theater with four screens sits on Eaton Street. Make sure you arrive early to make sure your group can snag seats together.

If there’s nothing showing that piques your interest at the Tropic – which specializes in independent, international, and classic films – you can also head to the Regal Key West. Located in the commercial district on the northeast corner of Key West, the Regal is your best bet for a new release.

6) Museums

Museums are the quintessential rainy day activity. Happily, Key West has plenty to choose from. Most Key West museums are located quite close together near the waterfront and Mallory Square, so it’s easy to visit multiple museums if the rain persists.

Mel Fisher Maritime Museum

Mel Fisher was a 20th century treasure hunter who famously located the wrecks of two 17th century Spanish galleons in the Gulf of Mexico between Key West and the Dry Tortugas. You learn more about Fisher’s work, see some of his treasures, and also learn about the Caribbean slave trade in this waterfront museum.

Key West Museum of Art and History

Located in the beautiful red brick Key West Custom House, this two-story museum is operated by the Key West Art and History Society. It’s the place to go if you’re interested in the history of Key West.

San Carlos Institute

Learn about Key West’s connection with Cuba at the San Carlos Institute on Duval Street. Built as a gathering place for Key West’s Cuban exiles, you can visit this Cuban heritage center to learn about the history of Cuba. Admission is free.

Shipwreck Treasure Museum

A small (but spendy) museum devoted to Key West history of shipwrecks and treasure. General consensus is that the best part of this museum is the observation deck at the top of a 65’ tower. If you want to enjoy the 360 degree views of the island at the top, pack your ponchos!

USCGC Ingham

This retired United States Coast Guard cutter served in both World War II and Vietnam. Now a National Historic Landmark, the prestigious ship spends its retirement docked in Key West as a museum ship. The exhibits are higgledy-piggledy and don’t tell a cohesive story. However, there is a designated “rain route” through the ship so you can see the highlights and stay dry.

7) Indoor Family Activities

If you’re looking for something a little more hands on than a museum, try some of these kid-friendly activities.

Florida Keys Eco-Discovery Center

We found this center had very limited hours when we visited in December, but if it does happen to be open, it’s a great place to learn about the Florida Keys National Marine Sanctuary. You also can’t beat the free admission price. While the center mostly offers exhibits, many of which are interactive, they do bring out educational carts on weekends.

Key West Aquarium

One of Key West’s first tourist attractions, the Key West aquarium is home to sharks, stingrays, turtles, jellyfish, and more. There’s also a touch tank. The aquarium offers various themed tours throughout the day.

Key West Butterfly and Nature Conservatory

A beautiful conservatory near the Southernmost Point Buoy landmark, the Key West Butterfly and Nature Conservatory is home to more than 50 species of butterflies as well as exotic birds including two flamingos! It’s an excellent way to immerse yourself in nature when Mother Nature herself isn’t cooperating with your vacation plans.

8) House Tours

Despite its small size, Key West has many historic houses to tour beyond the Hemingway House and Truman Little White House.

Audubon House and Tropical Garden

Contrary to what the name indicates, the famous American naturalist and artist John James Audubon never own or even set foot in this house. However, during an 1832 visit to Key West, he used the home’s gardens as a setting for a few of his paintings. Today the historic home, which dates back to the late 1840s, is decorated with Audubon’s paintings and open for tours.

Hellings Curry Museum

Located right on Duval Street in a brick Victorian mansion, Hellings Curry Museum is the house museum connected with the Key West Woman’s Club. The house tells the story of Eleanor Curry Hellings who built the house with her husband in 1892. Tours are held Monday – Friday during the winter season, and Tuesday – Thursday from May 1 – October 31.

Oldest House

Houses tend not to last super long in Key West. Between hurricanes and fires, homes from the early days of Key West in the 19th century were pretty well doomed. However, a small, nondescript conch cottage from 1829 has survived. Originally built on Whitehead Street, the house has sat on Duval Street since the 1830s. The house and gardens are open daily for tours.

Tennessee Williams House Museum

The famous American playwright, Tennessee Williams spent much of life visiting or living in Key West. Today, the Key West Art and Historical Society operates Tennessee Williams Museum on Truman Avenue. The museum is a scale model of Williams’ small Key West home and filled with exhibits about his life and works.

9) Shop

Like Santa Fe, New Mexico, Key West fancies itself a bit of a “city different.” (After all, this is the island that briefly succeeded from the United States in 1982.) As you might expect, Key West embraces the quirky and artistic and happily, that means the town has enough galleries and boutiques to fill days of rainy day shopping.

Some favorite Key West shops to check out are Our Key West, Art on Duval, and Wyland Gallery. Don’t miss the massive, and extremely lifelike, bronze animal sculptures at Wyland Gallery!

10) Drink

By far, the favorite rainy day activity for Key West visitor is drinking. Similar to Savannah, Key West is a party drinking destination and many Key West visitors take rain as a permission slip to while away the day at a Duval Street bar like the famous Sloppy Joe’s. Many Key West bars offer live music.

We opted for the quieter Roost cocktail bar, a hole-in-the-wall bar just off Duval Street on Fleming Street. Another great option is the First Flight Brewery located in the original headquarters of Pan American World Airways. It feels only appropriate to have a flight of the beers brewed on site at First Flight.

11) Take a class

You can use a rainy day as an opportunity to come home from Key West with some new skills.

First Legal Rum Distillery Mojito Class

Hit up Key West First Legal Rum Distillery for their mojito class. Made with Kermit’s key lime juice, you’ll spend about an hour learning how to craft the perfect mojito. Of course, you’ll get to drink your concoction at the end.

Key Lime Pie Class

To learn another way to use key lime juice, attend a pie making class at Key West Key Lime Pie Company. Everyone in your group will go home with a mini key lime class, not to mention a bunch of professional pie making tips.

Conclusion: Best Things To Do in Key West When It Rains

The good news is that it rarely rains for long in Key West. While we experienced rain almost every day during our week in Key West, there was only one day where it rained all day. (It did add up to over 1” so it was no joke!)

However, more often than not, rain showers in the Keys are fairly short lived. When clouds turn grey, just duck inside to one of the activities suggested in this post. By the time you emerge, it’ll likely be partly sunny again.

While I compiled this list to help folks in Key West bummed out rainy weather, so many of these activities should be included on any Florida Keys itinerary. Even if you have sunshine during your entire visit, you definitely don’t want to miss Key West indoor activities like Hemingway Home, Truman Little White House, or shopping in the unique galleries and shops.

I hope this post helps you make the most of your time in Key West, rain or shine!