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Rainy Day Activities in Key West

Group tour inside the Key West Shipwreck Museum

With most of our Old Town Trolley – Key West conductors being longtime Floridians, we’ve seen our fair share of rainy days. We’re also keen on Key West culture and know how to make every visit worthwhile, even if the skies turn gray.

If you check the weather for your upcoming trip and realize there’s a high chance of rain, simply pack an umbrella or poncho and remain calm. The rainy day activities in Key West happen to be some of the top attractions around the area. When you’re vacationing in the Florida Keys, there’s nothing that should put a damper on your stay. With our rainy day roster, you’ll have plenty of things to do on a rainy day in Key West.

  • Admissions Admissions
  • Shopping Shopping
  • Dining Dining
  • Entertainment Entertainment

Explore Things to Do On a Rainy Day in Key West

Key West Sails to Rails Museum frontSails to Rails Museum

Embark on a journey through Key West’s maritime past at the captivating Sails to Rails Museum. Discover the transition from sailboats to steamships and railways that shaped the island’s history. Explore artifacts, lift a real silver bar, and delve into maritime tales. Immerse yourself in Key West’s heritage with a Fort Jefferson diorama, offering a glimpse into its strategic importance.

Rainy Day Activities in Key WestSee a Movie at the Tropic Cinema

Let’s start with one of the most classic rainy day activities: seeing a show at the movie theater — but not just any theater, the Tropic Cinema in Key West. The theater’s Art Deco style sparkles, its neon accents add a bright quirk, and of course, the quality independent films and cinematic classics are the reason travelers and locals love to see a show at the Tropic Cinema.

rainy season key westHave a Drink and Play Games at the Waterfront Brewery

Rainy day activities in Key West aren’t too hard to come by, but it is hard to come by a brewery as unique as the Waterfront Brewery. Located in the historic Key West Bight, the craft brewery includes a ton of old-school arcade games. But they don’t play games when it comes to their full menu, featuring favorites such as the shrimp and avocado BLT, Cuban BBQ pork, and of course, key lime pie. It’s one of Key West’s most delicious things to do on a rainy day.

Key West MuseumTake a Walk With the Butterflies

Of all the rainy day activities in Key West, nature enthusiasts will love the Key West Butterfly and Nature Conservatory. It’s one of the few indoor rainy day activities that makes you feel like you can bring the beauty of outside, in. Wear bright colors if you want to make friends with a butterfly — stand still, and they’ll land on you for a magical moment.

Trolley Tour in Key WestExplore the Island With Old Town Trolley Tours

One of the best things to do on a rainy day during vacation is to keep exploring. Key West’s most popular tours are sure to take you and your travel team around the city, rain or shine.

Old Town Trolley – Key West stops at some of the most popular attractions in the city, with our seasoned conductors at the helm. You can hop on and off at Key West’s Bahama Village Market, Fairfield Inn and Mallory Square. And the world-famous Conch Tour Train has been taking visitors around the island since 1958, a great way to get to and from the city’s rainy day activities.

Truman Little White House

Visit Florida’s only presidential museum right here in Key West, rain or shine! Spend an hour or two learning about Harry S. Truman’s presidency and winter White House. Truman spent 175 days in Key West during his time in the Oval Office and has deep ties to the island paradise.

Museum in key westCustom House Museum

The Key West Museum of Art & History at the Custom House is one of Key West’s historic tourist attractions. Museums offer an incredible experience any day, but they’re true treasures when you’re in need of things to do on a rainy day for your vacation. Journey through Florida’s most notable history, painted and wooden artwork, and more with the site’s exhibits, films and tours.

rainy day activities The Hemingway Home

The Hemingway Home and Museum stands out as the perfect pick-me-up out of our favorite rainy day activities in Key West. Old Town Trolley – Key West raves about this experience because of its stories of the great writer, legendary history and its famous polydactyl (six-toed) cats. Hemingway’s first six-toed cat, Snow White, was gifted to him by a ship’s captain. Today, about 60 polydactyl cats roam the grounds, greeting those who visit the National Historic Landmark.

things to do on a rainy day Duval Crawl

For travelers 21 and up, rainy day activities in Key West wouldn’t be complete without a few options for cocktails. As long as you pack your umbrella, you’ll be able to stay dry as you barhop on Duval Street.

Delight in the island’s delicious drinks at the best bars on Duval. Try a spiked banana split at The Rum Bar, mojitos at Willie T’s or drink up at the Mardi Gras-themed classic, Fat Tuesday.

Indoor Activities Park Yourself on a Porch to Eat, Drink or Sightsee

Sometimes the best rainy day activities are the simplest. Here’s how to take a moment to appreciate your surroundings in Key West, even if it rains. Park yourself and your group on a porch and enjoy the rhythm of the rain and rolling thunder. There are plenty of eateries and bars around the island with covered decks, so you can keep your vacation going despite the rain.

fun things to do on a rainy day Mel Fisher’s Treasure Museum

This is one of the rainy day activities in Key West that you’ll truly treasure. At Mel Fisher’s Treasures, you’ll learn the story of a man who dedicated his life to the hunt for precious valuables. Opened in 1992 by Fisher’s daughter, the museum’s exhibits focus on the maritime history of Florida and the Caribbean. You’ll leave knowing all about Fisher’s finds. Earn your sea legs at one of the most popular rainy day activities in Key West.

Indoor Activities Key WestKey West Aquarium

The Key West Aquarium is the perfect outing for any visitor looking for rainy day activities in Key West. With shark feedings, guided tours, a touch tank, a shark exhibit and more, there’s so much to see as you walk through the aquarium.

If you’re traveling solo, you can take your time seeing the marine life. Planning the trip for the family? When kids are traveling as well, it’s important to have things to do on a rainy day in mind. The aquarium is exactly what they’ll need to cheer up if it rains on your original plans.

rainy day activities in key westPier House Resort & Spa

We get it, you may not want it to rain during your trip. But if it does, nothing will melt the stress away like a day of pampering at Pier House Resort & Spa. Whether you book a room or suite and stay with the Pier House team until the sun sets on your vacation, or you spend a day going totally tranquil with a treatment offered by the full-service spa, rainy day activities in Key West don’t get more soothing than this.


When is the rainy season in Key West?

Key West averages 44 inches of rain yearly, slightly higher than the nation’s 38-inch average. The island tends to have the most rain between June and November, but travelers should plan for things to do on a rainy day no matter when they visit.

What is the best time to visit Key West?

For travelers who prefer to avoid the crowds, book a trip to Key West between March and May for a quieter experience with less hubbub as you explore the city. If you vacation to the island between June and November, plan for a few rainy day activities, as these months include the unpredictability of hurricane season.

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