It’s May in the Florida Keys, and honestly? It’s a great time to pack your cutest sunhat, escape the winter months, and embrace full-on island living. We’re talking beautiful beaches, fresh food, street performers with questionable juggling skills, and maybe even a six-toed cat or two.
So if you’re wondering what to expect in Key West in May, pour yourself a rum punch and read on.
Key West Weather: Mild Temps, Clear Skies & Just Enough Sweat
Let’s kick it off with the weather—because if we’re being real, that’s half the reason you’re here (the other half is key lime pie, obviously).
May in Key West is like Goldilocks weather. Not too hot (August has that honor), not too cool (January, we see you). We’re serving up average high temperatures around 85°F, with blissfully breezy evenings dipping into the upper 70s. You’ll get sunny days, clear skies, and just enough humidity to remind you your hair has no chance.
Rain? Barely. The rainy season is still snoozing, and hurricane season doesn’t start until June—though a tropical storm might try to sneak in early for a cameo at the end of the month.
Bottom line: It’s the best time to bask in that Atlantic Ocean breeze, work on your tan, and act like you haven’t checked your email since February.
Getting to Key West: Your Road to Paradise (Literally)
If you’re driving down from Key Largo, prepare for the most Instagrammable road trip of your life. The Overseas Highway is what happens when a postcard and a playlist have a baby. Bonus points if you stop at Bahia Honda State Park—you won’t regret it.
Prefer to fly? The newly updated Key West International Airport gets you in quick. Once you land, skip the rental car drama. Everything’s walkable or bikeable, and let’s be honest—you didn’t come to paradise to circle the block looking for a parking spot.
If you’re feeling fancy, hop aboard the Key West Express from Fort Myers. It’s a boat ride, a sightseeing tour, and your first cocktail opportunity—all in one.
Where to Stay: May = Fewer Crowds + Better Hotel Rates
Let’s talk lodging. May is that magical moment after the peak tourist season but before the summer season kicks in with its sticky embrace. Translation? Hotel prices drop, hotel rates ease, and there are finally open chairs at the pool.
Want to be close to the action? Stay on or near Duval St. (cue the cocktails). Want something a little quieter? Head toward Sunset Key Cottages or snag a waterfront view at Marker Key West Harbor Resort.
And if you’re stressing over finding the “perfect” place, just remember: it’s Key West. The only wrong choice is not going at all.
11 Best Tips on Choosing a Hotel Room
One of my favorite ways to price compare is with Kayak. In one quick search, I can see what’s available and hotel prices.
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Things to Do in Key West in May (Besides Becoming a Mojito Connoisseur)
There is always something happening here—like popular events, musical performances, and surprise iguana sightings (they’re just part of the welcome committee).
Here’s your May fun list:
- Catch the sunset celebration at Mallory Square—complete with local artisans, fire jugglers, and people in parrot costumes. It’s a vibe.
- Grab a big ol’ slice of key lime pie. It’s practically a rite of passage.
- Visit Fort Zachary Taylor Park for some beach time and one of the best sunset views around.
- Wander down Duval Street (or Duval St. if we’re feeling SEO-fancy). Pop into bars, art galleries, or both. It’s called balance.
- Tour the Ernest Hemingway Home and meet his cats. They have six toes. It’s weirdly charming.
- Book a ferry to Dry Tortugas National Park. Picture crystal-clear blue water, snorkeling, and a legit historic fort in the middle of the ocean. It’s like a real-life pirate adventure minus the sword fights.
Oh, and the water temperatures? A steamy 82°F. It’s like bathwater, but better—because you’re in paradise.
Calling All Music Lovers: The Key West Songwriters Festival
If there’s ever a time for music lovers to visit Key West, it’s May. The Key West Songwriters Festival is the largest festival of its kind and officially the coolest thing to happen this side of Fantasy Fest. Now in its 29th year, it’s part concert series, part beach party, and part “OMG is that a Grammy winner playing in a dive bar?!”
You’ll hear future chart-toppers, heartfelt acoustic sets, and maybe even stumble upon a show featuring someone like Kacey Musgraves (seriously, it’s happened). From rooftop venues to oceanfront stages, it’s an all-access pass to chill, swaying with your drink in hand.
Spoiler alert: It’s not just a festival—it’s a whole Key West vacation experience.
Events, Art, Markets & Quirky Goodness
Not into music? Don’t worry, there’s more. (It’s Key West and the Florida Keys. We don’t do boring.)
- Sip and stroll during Walk on White and the Morada Way Art Walk—featuring everything from wood carvings to live painting and most-recognized folk artists in the Keys.
- Visit the Studios of Key West for rooftop mingling and seriously cool local exhibits.
- Bring the fam to the Truman Waterfront Farmers Market every Thursday for fresh produce, sunshine, and the best conch fritters around.
- Snuggle goats and sloths (yes, really) at the Monroe County Sheriff’s Animal Farm.
- Catch film screenings under the stars or toast Mother’s Day with mimosas and mermaids—your call.
Stick around for Memorial Day weekend and enjoy one last hurrah before June rolls in like a sweaty handshake.
Why May Might Be the Best Time of the Year to Visit
We’re not saying May is the only time to come to Key West—but we’re also not not saying that. Between the mild temperatures, fewer crowds, and special events, it’s kind of the better time to be here.
You’ll find long daylight hours, tropical blooms in full swing, and an itinerary that fills itself. Whether you’re here for art, history, sunsets, or just some fresh food and a cold drink in your hand—you’ve picked the perfect time of the year.
And if you can’t make it in May? Don’t worry—we’ve got more fun coming:
- Fantasy Fest in October
- Hemingway Days in July
- The Key West Literary Seminar
- Conch Republic Independence Celebration in late April
- Or ring in the New Year with a drag queen descending from a giant shoe on Duval Street (Google it. You won’t be sorry.)
Ready to Plan?
Whether you’re flying, ferrying, or road-tripping, May in Key West is calling. The sunsets are waiting, the pie is chilled, and the cats are oddly polydactyl.
So… what are you waiting for?
Can’t make it in May? Then check out what’s happening the rest of the year
April – Annual Conch Republic Independence Celebration
July – Hemingway Days
What is happening in May? Let’s see…
Studios of Key West: Isaac Valdes – The Way it Was – May 1 – 29, 2025
Experience the historical charm and vibrant culture of Old Key West through intricate wood carvings. This exhibition captures the essence of Key West’s bygone days, depicting its unique architecture, lush landscapes, and colorful local life. 533 Eaton St.
I.CARE: Trash Derby & Festival – May 1 – 4, 2025
I.CARE’s Trash Derby, sponsored by the National Marine Sanctuary Foundation in support of Goal: Clean Seas, brings teams of environmentally-conscious debris collectors in divisions including dive charters, private boat owners and land lovers. After two days of trash collecting, there is a free festival Sunday at Founders Park, mile marker 87 bayside from noon to 6 p.m. The festival is open to the public. There is to be an awards ceremony to include cash and other special prizes. The festival features live music, food vendors, games and activities, raffles, a silent auction and exhibitors including local organizations helping to restore Keys coral reefs.
Studios of Key West: First Thursday Open House – May 1
Studios of Key West invites all to visit during First Thursday Open House, where art, conversation and community come alive after hours. Wander through the galleries showcasing the newest exhibitions, sip drinks under the stars at the Hugh’s Rooftop terrace, and explore the creativity in the third-floor artist studios. Take in the vibrant energy, connect with fellow art lovers, and discover hidden gems at Books & Books. Mingle, marvel, or make memories!
Coffee Butler Amphitheater: Nate Smith with Chase Matthew – May 1
Vocal powerhouse Nate Smith has achieved remarkable success after just a few years on the country music scene with No. 1 hits including Whiskey on You, World on Fire and Bulletproof. Joining him for the amphitheater show taking place during the 2025 Key West Songwriters Festival is Chase Matthew, a rising star of the Nashville music scene. Doors open 6:30 pm.; show 8 p.m.
Truman Waterfront Farmers Market – Every Thursday – May 1
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
Marathon Community Theater: The Siegel – May 8 – 24, 2025
The story follows lovesick Ethan who plans to ask Alice’s parents for permission to marry her, but there’s one catch. Ethan and Alice broke up two years ago. Alice, reeling from having worked for a failed political candidate, is seeing someone else, but Ethan remains undaunted.
Key West Theater: Paula Poundstone – May 9
Iconic comedian Paula Poundstone is known for her smart, observational humor and a spontaneous wit that has become the stuff of legend. She performs at Key West Theater for one night.The show, originally scheduled for Jan. 9, was rescheduled due to the California fires. Doors open 7 p.m.; show at 8 p.m. 512 Eaton St.
Key West Outdoor Movies – May 9
Key West Outdoor Movies presents a family-friendly film (to be named) at the parade grounds at Fort East Martello, 3501 S. Roosevelt Blvd. The grounds open at 5 p.m. with free admission. Food and drink will be available for sale by vendors onsite, and there will be free popcorn and activities for all. Bring low chairs or a blanket. The movie starts at dusk. This is the season finale for Outdoor Movie Night
Sheriff’s Animal Farm Open House – May 11
Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Animals include a capybara, possum, sloths, goats, birds and many more. Visits are free of charge, but donations of cash or fresh produce are always welcomed. Stock Island Detention Center, 5501 College Rd.
Walk on White Third Thursday Art Walk – May 15
Explore an array of arts-focused offerings at more than 20 locations showcasing the works of painters, photographers, sculptors, ceramic and mixed media artists, and artisan jewelry makers at this monthly third Thursday event from 6 to 9 p.m. Take in views of beautiful island architecture, exhibit openings, creative demonstrations, musical, literary and performance offerings and complimentary libations. White Street between Southard and United Streets.In May, there will be a bike parade down White Street for American Bike Month.
Key West Theater: Duane Betts & Palmetto Motel – May 15
Duane Betts, son of Dickey Betts of Allman Brothers Band fame, performs guitar-slinging, story-driven American rock and roll along with Palmetto Motel. Doors open 7 p.m.; show at 8 p.m. 512 Eaton St.
Truman Waterfront Farmers Market – Every Thursday– May 15
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
Morada Way Third Thursday Art Walk – May 15
The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. This Thursday, enjoy a holiday-flavored edition of the art walk with Keys-inspired fine artists, vendors, residents, and visitors congregating on Morada Way in Islamorada. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine and listening to music, in the area between mile markers 81 and 82 at 151 Morada Way.
Keys100 Ultramarathon Races – May 17 – 18, 2025Keys 100 is a 100-mile point-to-point running race from Key Largo to Key West. Both teams and individuals compete. There is also a 50-mile option from Marathon to Key West and a 50k individual race from Big Pine Key to Key West. All races finish at Higgs Beach on the Atlantic in Key West. 100-mile races start at Divers Direct in Key Largo, MM 99.8, and 50-mile races start at Marathon Garden Club.
Truman Waterfront Farmers Market – Every Thursday – May 22
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
Sheriff’s Animal Farm Open House – May 25
Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Animals include a capybara, possum, sloths, goats, birds and many more. Visits are free of charge, but donations of cash or fresh produce are always welcomed. Stock Island Detention Center, 5501 College Rd.
Truman Waterfront Farmers Market – Every Thursday – May 29
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
