It’s May on the Island and there is no shortage of warm weather, delicious cocktails, and fun things to see and do. Key West is, well the best place to visit, no matter the time of year. So what can you expect in Key West in May?
Key West Weather
Let’s begin with the first question… weather. May isn’t the hottest month, that’s August. And, it’s not the coldest month of the year, that’s January. But, you can expect average temperatures in the mid-80s. The average high temperature may be at 85, but the lows will only drop into the upper 70s. Yep, pleasant weather is usually expected for the month. For those still having cooler weather, May is the perfect escape for those still feeling the bite of winter months.
Humidity hasn’t crept in yet. But, it will start to increase over the month. By the end of the month, the humidity will begin to feel like the rest of the summer months. Not too many rainy days usually in May. The average is at 5 a month. This means there are a lot more sunny days this month. The Atlantic Hurricane Season will begin officially in June, but in the meantime, you may see a tropical storm roll in.
Getting to Key West
Heading down to Key West from Key Largo? There is a lot to see, so plan to take your time and explore.
Flying into Key West International Airport? Don’t worry about a car. Grab a ride to your hotel and then plan to explore the Island on foot. You are on vacation. No need to stress yourself over finding a parking spot.
Hotel Rooms
I know, hotels can be pretty spendy, especially in Key West. Do a bit of research. Decide where you want to be located – Old Town, New Town, etc. What amenities can you not live without? What’s your price range? That usually helps me find a great place to stay.
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.
Check out our Resource Page for more!
Hotel room prices vary, depending on demand. So, during peak season, or the high season, the prices will be higher. Think late December through March. May is a great time to explore the Island before the humidity and rainy season hit.
Things to Do
There is always something to do in Key West. Head over to Mallory Square for the sunset celebration and watch the street performers. It’s a must-do no matter how many times you have visited Key West.
Grab a slice of Key Lime pie.
Explore Fort Zachary Taylor Park. Be sure to stay for sunset. One of the best views of sunset can be seen from the park.
Walk down Duval Street and window shop. Or actually, shop in one of the art galleries. Or pop into Sloppy Joe’s or Irish Kevin’s for a cold drink and enjoy some live music. A good time for sure!
Book a trip to the Dry Tortugas National Park. These trips book up far in advance so book before you arrive to make sure you get a seat.
Yankee Freedom Ferry to Dry Tortugas
Or head out to explore the waters around Key West. The average water temperature for May is a very comfortable 82 degrees. Perfect for water sports.
Calling all music lovers, May is hands down the best time to visit Key West, all thanks to the fabulous Songwriters Festival. Picture this: five days of pure musical magic, where the island vibrates with the melodies and lyrics of talented songwriters from all over.
With intimate performances in cozy bars, sunlit gardens, and oceanfront stages, you’ll get up close and personal with the artists behind your favorite hits. It’s an event where the line between performer and audience blurs, making every moment feel special and unique.
Trust me, the vibe is electric, the stories behind the songs are captivating, and the setting is nothing short of paradise. So, come with your love for music and be prepared to discover new tunes, meet amazing people, and create memories that will last a lifetime.
Explore the Ernest Hemingway home. Meet the 6 toed cats. Or any of the other historic sites in town.
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…
THE GATES HOTEL: REV UP — MEET UP & WRITE – May 1
The Gates Hotel hosts a special event Wednesday afternoon from 1 to 5 p.m. as part of the Key West Songwriters Festival. It’s a meet-and-greet with songwriters, plus attendees will have a chance to help the songwriters create an original song for the event. Featured artists include the Andy Wescott Band, James Slater, Rob Snyder, Jobe Fortner and Ryan Nelson. Also in attendance will be members of CreatiVets, whose mission is to empower wounded veterans to heal through the arts and music. Free to attend. 3820 N. Roosevelt Blvd.
STUDIOS OF KEY WEST: FIRST THURSDAY OPEN HOUSE – May 2
During the First Thursday Open House event, the Studios keep the lights on late and throw the doors open to celebrate the newest work in its galleries. Stop in to say hello, relax with a glass of wine on the rooftop terrace, tour the third floor artist studios and see the just-installed exhibitions in the various galleries. 6 to 8 p.m. at 533 Eaton St.
COFFEE BUTLER AMPHITHEATER: COLE SWINDELL – May 2
Key West Songwriters Festival presents Cole Swindell in concert May 2. Doors open 5:30 p.m.; Showtime 7 p.m. Ticket start at $59. 21 Quay Rd.
THE STUDIOS OF KEY WEST: GALLERY TALK WITH ARTIST ANTHONY MANCUSO – May 3
All are welcome to this free, family-friendly Key West Outdoor Movie Night featuring Pixar’s “UP” on the lawn at Fort East Martello, 3501 S. Roosevelt Blvd. Doors open at 6:30 p.m. with the movie starting at dusk. Bring a blanket or a low-profile chair. Popcorn is free.
COW KEY BRIDGE RUN: COW WARS 2024 – MAY THE 4TH BE WITH MOO! – May 4
Dress up in your best bovine costume and trek across the infinitely short Cow Key Channel Bridge. Get in the MOO-d from 9 to 11 a.m. before the “race” at the Bloody MOO-ey party at the Rum Row bar at The Gates Hotel. The entire herd will move over to stage at the starting area in front of the bridge between 11 a.m. and 12 p.m. At 12 noon, the race starts with cows away! Everyone is invited back to Rum Row and the Sunset Green Lawn for an after-race party and awards ceremony. Sign-up includes a race bib. Commemorative T-shirts will be available for purchase at the pre-race party. All proceeds benefit the MCSO Animal Farm and the Highgate Foundation.
TALK DERBY TO ME – May 4
Support the Key West Mounted Police Unit at the 7th annual “Talk Derby to Me” event at The Gardens Hotel, 526 Angela St. Dress up to compete in the best costume, best hat and best couple contests. Get photos with the Key West P.D. horses and officers, and enjoy mint juleps and food. $25 donation at the door.
SCHOONER AMERICA 2.0: STARRY NIGHT STARGAZING SAIL – May 4 – 5, 2024
Sail through Key West waters by starlight on this stargazing sailing adventure aboard the 105-foot Schooner America 2.0, featuring live narration from NASA Solar System Ambassador and Key West resident, Kevin Gallagher. Trip departs at 9:15 p.m. from the dock at Key West Bight, 202 William St.
RUN FOR RHONDA 5K – May 5
Run or walk your way through Key West on Cinco de Mayo for the first annual Run for Rhonda. Starting and finishing at Truman Waterfront Park, the race will be followed by a fabulous post-race party with DJ Jimmy Jam, adult and non-alcoholic beverages, festive food, a raffle and more. The run honors the legacy of Key West resident Rhonda Flores and supports a college scholarship for a participant in the Take Stock in Children program.
SLOPPY JOE’S 87TH ANNIVERSARY AT THE CORNER OF DUVAL AND GREENE STREETS – May 5
Schooner Wharf Bar’s 25th annual Cinco de Mayo celebration takes place from 7 p.m. until midnight. Win a prize for the best Mexican hat, compete in the Super Hot Taco Eating Contest for prizes, and party with live music by the Cool Coconuts Band. 202 William St.
THE MARKER: CINCO DE MAYO MARGARITA BATTLE – May 5
Gather by the pool at The Marker, 200 William St., at 3 p.m. for the 2nd annual island-wide margarita battle. Bartenders from The Starboard Restaurant & Bar at The Marker, Southernmost Beach Cafe, The Gates Hotel and 24 North Hotel shake up their tastiest margaritas, and you get to be the judge. Live music by Les Greene and The Swayzees.
TROPIC CINEMA: THE MARCHING CONCHS IN LONDON PREMIER – May 8
A film documenting the Key West Marching Conchs’ journey “across the pond” to appear in the January 1, 2024 New Year’s Day Parade premiers at Tropic Cinema with a 5 p.m. showing. The film was shot and edited by Key West High School’s student-run Conch 5 Studios.
Join Key West native and folk artist Wayne Garcia for an evening of storytelling themed “Key West Ghost Stories: They Only Follow Us at Night.” He will delight the audience with tales of Old Key West, his memories from growing up, and many of the island’s most infamous characters. His stories will be accompanied by his colorful wood carvings and vintage photographs depicting Key West’s incredible past. 6 to 7 p.m. at Tropic Cinema, 416 Eaton St. Purchase $15 tickets online.
REEF RELIEF ANNUAL LUAU FUNDRAISER – May 11
Reef Relief holds its annual luau celebration from 5 to 8:30 p.m. at Lagerheads Beach Bar & Grill, located at 0 Simonton St. Enjoy live music from Gary Hempsey, games, a raffle, a silent auction and more.
TENNESSEE WILLIAMS THEATRE: ONE NIGHT OF QUEEN – May 12
For over 20 years Gary Mullen and The Works have been performing their world-renowned “One Night of Queen” live concert. Gary Mullen & The Works will have you dancing in the aisles during their show, while the band pays tribute to the stage theatrics, showmanship, and music of Rock & Roll Hall of Fame inductees: Queen. Tickets $45 to $135. Show at 8 p.m. 5901 College Rd.
SHERIFF’S ANIMAL FARM OPEN HOUSE – May 12
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. Visits are free of charge, but donations are always welcomed. Stock Island Detention Center, 5501 College Rd.
STUDIOS OF KEY WEST: CRAIG FOSTER DISCUSSES HIS NEW BOOK, AMPHIBIOUS SOUL – May 17
From the creator of the beloved Academy Award winning documentary “My Octopus Teacher” comes “Amphibious Soul,” Craig Foster’s thrilling memoir of a life spent exploring the most incredible places on Earth – from the Great African Seaforest to the crocodile lairs of the Okavango Delta. Foster reveals how we can attend to the earthly beauty around us and deepen our love for all living things, whether we make our homes in the country, the city, or anywhere in between. $40 ticket includes a copy of the book. Doors open at 6 p.m., talk at 7 p.m.
BAYVIEW PARK: LAW ENFORCEMENT MEMORIAL CEREMONY – May 17
Honor those officers who have given their lives in the line of duty during a Law Enforcement Memorial Ceremony organized by the Monroe County Sheriff’s Office, 5 p.m. at Bayview Park, 1320 Truman Ave.
KEY WEST TROPICAL FOREST & BOTANICAL GARDEN: RUM INFUSED ADULT SCAVENGER HUNT – May 18
Don your best pirate or mermaid costume for a night of rum-infused fun during a scavenger hunt throughout Key West Tropical Forest and Botanical Garden. Teams will be created to follow the scavenger hunt rules, with points given for the most items found within one hour. Proceeds benefit funding bus transportation for Monroe County school children’s educational trips to the garden in the coming year.
REELIN’ FOR THE CAUSE KIDS FISHING TOURNAMENT – May 18
The tournament raises awareness about congenital heart defects and provides funds to support families with infants born with these disorders. Registration is now full. For registered children, check in at 9:30 a.m. at Edward B. Knight (White Street) Pier. Rods, reels and bait provided. Lines in at 10 a.m.; awards ceremony at 11:45 a.m. Awards for biggest fish in each age group: 3 to 5; 6 to 8; and 9 to 13. Spectators may take part in the silent auction at the pier during the tournament.
SCHOONER WHARF BAR: MINIMAL REGATTA – May 26
Watch sailors make a splash in homemade vessels made from plywood and duct tape in the craziest regatta you’ll ever see on the waters of Key West Bight. Watch from the Historic Seaport walkways near Schooner Wharf. 12 noon at 202 William St.
SHERIFF’S ANIMAL FARM OPEN HOUSE – May 26
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. Visits are free of charge, but donations are always welcomed. Stock Island Detention Center, 5501 College Rd.
