Thinking about escaping to paradise? Well, June might just be the best time of year to visit the crown jewel of the Florida Keys. Picture this: palm trees swaying, plenty of sunshine, pool parties by day, and a sunset cruise at night. Yeah, it’s a vibe.
Let’s Talk June Weather in Key West
June brings average high temperatures in the upper 80s, with warm waters perfect for all your water sports dreams—from paddleboarding to snorkeling with dolphin fish (yep, they’re a thing and not just a dolphin). Even though it’s the start of hurricane season, the rainy season in Key West is more like “surprise sprinkles” than downpours. And that tropical storm risk? It adds a little drama to your vacation photos.
Weather data tells us there are only about 7 days of rain in the month of June, and the rest? Just the kind of hot weather you want when you’re on a tropical island.
Rainy Day? Still a Great Time!
Even if the skies open up, Key West knows how to make a rainy day sparkle. Explore the Florida Keys Eco-Discovery Center, check out some Key West Pride Follies, or sip rum under cover while planning your next move. You’ll find the best places to ride out a storm are often the ones with live music, a view, and a cold drink.
Rainy Day Activities in Key West
What to Wear (Besides Your Most Fabulous Flip-Flops)
Key West’s unofficial dress code? Island casual—which basically means: pack your sundresses, linen shirts, and a smile. Throw in a swimsuit (or three), comfy walking shoes for your early stroll down Duval Street, and you’re golden.
Don’t forget something breezy for those full moon nights and summer solstice celebrations (hello, longest day of the year).
Pro tip: Bring light layers for ducking into the Key West Theater or Studios of Key West, where the A/C hits like a tropical storm.
More ideas on what to wear and what to pack for Key West
Getting Here
Flying in? The Key West International Airport drops you right into paradise—no stress, no layovers in Miami (unless you’re into that sort of chaos). Once you land, grab your luggage and say “aloha” to beautiful things—like sunshine, good vibes, and maybe a conch fritter or two.
Where to Stay: Smart Tips for the Not-So Peak Season
Technically it’s still tourist season, but you can score some of the lowest prices of the year if you’re savvy. Want an island experience on a budget? Look for mid-week deals and last-minute specials. We’ve got a whole resource page to help you unlock secret discounts.
You’ll find accommodations from Smathers Beach to the Truman Waterfront Park, all within easy reach of the action (and cocktails).
Check out our resource page to see if you can find any hotel deals
The Best Things to Do in Key West in June
Whether you’re here for the sunshine or the cultural diversity, there’s something for every kind of traveler in Island City. Here are a few must-do’s:
- Celebrate Key West Pride – This annual event is one of the most vibrant and welcoming in North America. Expect drag queens, pool parties, a dance party, and a champagne reception or two.
- Hit the Mango Festival – June is when those juicy mangoes are ripe and ready, and the island celebrates with a colorful series of special events (and plenty of opportunities to taste the best bite of the season).
- Soak up some Key West Art & History – Pop into the Custom House, Key West Lighthouse, and the Key West Museum of Art & Historical Society to escape the heat and enjoy the rich history.
- Catch some live music – From Sloppy Joe’s Bar (Ernest Hemingway’s old haunt) to laid-back patios with steel drums, there’s always a rhythm in the air.
- Sunset at Mallory Square – It’s the ultimate sunset celebration with performers, cocktails, and the most Instagrammable golden hour you’ll ever experience.
Want More Island Fun?
- Join a Key Lime Festival preview or vote for the best Key Lime Pie in town (trust us, it’s a heated debate).
- Shop from local artists during pop-ups at the Studios of Key West or galleries near Higgs Beach.
- Explore historic sites with a walking tour, or take a self-guided stroll and visit the southernmost point in the U.S.
Check out our must see and do list when in town!
June is Pride Month. Key West has an amazing celebration each year. It’s one of the best places to celebrate, Pride, Mangoes, and anything else!
Ready to Plan?
The best ways to experience Key West in June include leaning into the fun, staying cool with a drink in hand, and exploring every colorful, quirky corner. Whether you’re here for the natural beauty, the vibrant culture, or just a good excuse to break out your loudest tropical shirt, Key West delivers.
So pack light, plan loose, and prepare for a good time.
Summer Solstice Celebration at Mallory Square: June 1-20
Every evening in Key West, locals and visitors gather at the waterfront Mallory Square for the world-famous Sunset Celebration, to enjoy the unique gathering of skilled artisans, exciting performers, and local vendors — and to toast the setting of the sun. Beginning June 1, a colorful series of special events and performances will take place nightly from 7 p.m. until after sunset, leading up to the June 20 Summer Solstice, the official first day of summer.
Sheriff’s Animal Farm Open House – June 8
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.
Key West Gator Club Dolphin Derby – June 13 – 15, 2025
Anglers targeting dolphin fish can compete for $15 thousand in guaranteed cash prizes during the Key West Gator Club Dolphin Derby June 13 through 15. Tournament location to be announced. The team weighing in the heaviest dolphin fish takes home a grand prize of $5 thousand. Proceeds benefit scholarships for Key West High School graduates attending University of Florida.
College of the Florida Keys Swim Around Key West – June 14
Embark on an adventurous competitive swim – a 12.5 loop around the island. The pristine waters around Key West give swimmers great views of both the land and underwater life. Compete in different categories including solo swimmer, solo swimmers with fins, solo swimmers using a mermaid tail or a monofin, or gather your friends and compete in the relay category of 2-person, 3-person, 4-person, 5-person or 6-person teams. Not interested in the full island swim? Try some of the smaller races offered, a 6.1-mile swim, a 2-mile swim, a 1-mile swim or an 800-yard swim. Swims begin and end at Higgs Beach, 1000 Atlantic Boulevard.
Walk on White Third Thursday Art Walk – June 19
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.
VFW Fishing Tournament – June 20 – 22, 2025
VFW’s annual fishing tournament returns with over $75,000 in cash and prizes. The big change for 2025 will be that all registered boats are able to fish two days, with no separate registration required for each fishing day. Tournament events are held at the VFW post at 2200 N. Roosevelt Blvd.
Key West Pride – June 22 – 29, 2025
Celebrate Pride on the tropical island of Key West that is legendary for its laid-back style and its open and accepting atmosphere. This year’s event theme is “Still Rising,” honoring the history of the LGBTQ+ community. Along with Key West Art & Historical Society and the Stonewall National Museum, a special exhibit will showcase “50 Years: The Stonewall Uprising.” This year’s Pride also features late-night dance parties, historical tours of Gay Key West, daytime and sunset sailing excursions, a private beach party, pool parties, film screenings, drag performances, comedy night, a bar crawl by trolley and much more.
Hemingway Days – June 22 – July 27, 2025
Ernest Hemingway look-alikes, writers, anglers, and fans of the late author’s work are to gather in Key West for the annual Hemingway Days celebration. The festival honors the legacy of the American literary giant who lived and wrote on the island for most of the 1930s. Events include the legendary Hemingway Look-Alike Contest, the wacky Running of the Bulls on Sat. July 26, literary presentations, a commemoration of the 126th anniversary of Hemingway’s July 21 birth, a museum exhibit, a marlin tournament, a 5k run and paddleboard race, a street fair and more.
Sheriff’s Animal Farm Open House – July 22
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.
Studios of Key West: Mango Madness Annual Summer Members Show – until July 31. 2025
Every member of The Studios is invited to participate in the annual members’ exhibit, and the result is a bounty of creativity in every form and style imaginable. Artists are not asked to make work about mangoes exactly, but it is hoped that the work brings them – and you – similar joy. 533 Eaton St.
Truman Waterfront Farmers Market – Every Thursday
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.
Studios of Key West: First Thursday Open House
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!
What’s Happening Up the Keys
Coralpalooza – 10th Anniversary Celebration – June 5 -7, 2025
Held every year to honor World Ocean’s Day and World Reef Awareness Day, this event mobilizes hundreds of ocean lovers in Florida and around the world to take large-scale action aimed at restoring our planet’s disappearing coral reefs. It offers SCUBA-certified divers hands-on restoration opportunities while allowing snorkelers to explore the broader context of coral reef conservation.
Lower Keys Chamber of Commerce Dolphin Tournament – June 6- 8, 2025
The Lower Keys Chamber of Commerce presents the 32nd annual event where anglers contend for over $35,000 in cash prizes and awards. A special cash prize of $20,000 is awarded for the largest dolphin over 50 pounds — this prize is available only to the anglers on the first 50 boats registered for the tournament. Additional prizes await winners in open, ladies and youth divisions
Florida Keys Elks Ladies Dolphin Tournament – June 6 -7, 2025
Female anglers vie for cash and prizes for the heaviest weight of three mahi mahi in the 10th annual Ladies Dolphin Tournament. Tournament events are to be held at the Elks Lodge, mile marker 92.6 bayside in Tavernier.
REEF Ocean Exploration Center: Grand Opening– June 7 -8, 2025
The new REEF Ocean Exploration Center for Marine Conservation is to be unveiled June 7, 2025, in honor of World Oceans Day in a free grand opening celebration from 3 to 7 p.m. After the ribbon cutting, the center will be open with a variety of hands-on activities and demonstrations. Local food trucks and drink vendors will be there to add to the celebration. The center, located in the median of U.S. 1 at mile marker 98, is designed to inspire curiosity and wonder for the oceans, foster scientific research and collaboration, and serve as an immersive experience that helps everyone discover their unique role in protecting our blue planet.
Reef Relief: International Ocean Film Festival – June 7
A curated ocean-themed lineup of the most compelling, innovative short films from filmmakers around the world. Interactive Reception 5:00-6:15 PM Film viewing 6:15-7:45 PM Panel Discussion 7:45-8:15 PM Proceeds support Reef Relief’s Education and Conservation Program.
REEF Fish Out of Water 5k – June 8 – 14, 2025
Whether you’re an experienced runner or prefer a leisurely stroll, bike ride, or skate, this is a family-friendly event for all. The route follows the picturesque Florida Keys Overseas Heritage Trail, starting and ending at the Ocean Exploration Center, mile marker 98. Registered participants receive limited-edition gear, including a race shirt and custom fish-themed stickers. Even if you don’t register, join for the fun and the post-run celebration with coffee and snacks. This will be REEF’s sixth annual Fish Out of Water 5K event, but the first time an in-person gathering has been added as an option to this traditionally virtual event. Registration opens on April 1. All proceeds benefit REEF’s Ocean for All Fund.
World Oceans Day Tours: History of Diving Museum – June 8
Join the History of Diving Museum at 11 AM and 2 PM for a special guided tour of the exhibits! The tour is included in your admission price. June’s tours will be held in honor of World Oceans Day, and highlight pioneers in marine conservation such as William Beebe and Rachel Carson.
Ladies Tarpon Fly Tournament – June 10 -12, 2025
Connecting women worldwide through competition and conservation, this all-release fly fishing invitational tournament for women is held in Islamorada each June during the height of the tarpon migration. New teams are invited to apply for invitation consideration.
Father’s Day Dolphin Derby – June 13 – 14, 2025
This popular dolphin tournament with check-in on Friday and fishing Saturday pays out thousands in cash and prizes to the top four adults with the heaviest fish. Junior anglers age 15 and under vie for rod and reel combos.
Gold Cup Tarpon Tournament – June 16 – 20, 2025
The annual Gold Cup consists of 5 days of fly fishing out of Islamorada for the silver king. The hotly contested competition ends with the top angler and guide having their names added to the 62-year-old perpetual trophy. Headquartered at the Lorelei Restaurant and Marina, mile marker 82 bayside, the all-release fly fishing event is limited to 25 anglers by invitation only. Partial proceeds benefit the Guides Trust Foundation of the Florida Keys.
Free Immerse Yourself! Diving and Salvage Operations – June 18
Join the History of Diving Museum as it hosts Michael Carr, US Army Watercraft Master and Navy Diving and Salvage Officer. Michael will present on several salvage operations he participated in, as well as the physical and emotional demands on divers working on such wrecks. Presentation will be both in-person and virtual, and take place at 7 PM on June 18th at the History of Diving Museum, 82990 Overseas Hwy (MM 83 Bayside). Donations welcome. Info: (305) 664-9737; www.divingmuseum.org
University of Miami Sports Hall of Fame & Museum Celebrity Fishing Tournament – June 19 – 21, 2025
Anglers are invited to join UM sports celebrities to fish for the highest aggregate weight of 3 dolphin fish (mahi-mahi) and other species in this fundraiser for charities and the UM Sports Hall of Fame & Museum. Tournament events take place at several Islamorada locations. The public is invited to attend the tournament’s social events to meet and greet their favorite UM players. Find tickets and details online at CanesFish.com
Morada Way Third Thursday Art Walk – June 19
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.
Islamorada Fishing Club Captain’s Cup Dolphin Tournament – June 25 – 26, 2025
Teams of up to four anglers compete for top prizes with the total combined weight of three fish determining the winning team. If up to 25 boats register, first prize cash winnings can reach $25,000. Tournament activities are to be held at the Islamorada Fishing Club, 80939 Overseas Highway.
Florida Keys PBA Charity Dolphin Tournament– June 27 – 29, 2025
This fishing tournament is hosted by volunteers of the South Florida Police Benevolent Association and headquartered at Oceans Edge Resort and Marina on Stock Island, 5950 Peninsular Ave. Cash prizes for first- through fourth-place anglers are based on the number of entries, and increase as participation increases. Cash prizes are also awarded to top junior, female and PBA member. Over $15 thousand in prizes are to be awarded. The angler with the biggest tuna wins a rod and reel combo. Register online. Proceeds primarily benefit the Autism Society of the Keys and the Love Fund.
Blue Star Museums: History of Diving Museum – until September 1, 2025
To honor and thank those serving in the military, on Armed Forces Day the History of Diving Museum will hold complimentary guided tours included with your admission ticket. These will take place at 11 AM and 2 PM on Saturday, May 17. This date also marks the beginning of the 2025 Blue Star Museums Program, which offers free admission to active-duty military and up to five members of their family. Blue Star Museums begins on Armed Forces Day, Saturday, May 17 and ends on Labor Day, Monday, September 1.
History of Diving Museum Presents – Celebrating 20 Years! Featured Exhibit – until December 31, 2025
The History of Diving Museum’s new limited-time featured exhibit is open to the public! Starting May 21st, dive into the Museum’s 20th Anniversary Special Exhibit to learn about what it took to create the world’s largest collection of diving equipment on public display, how the Museum has evolved and grown over the past two decades, and what visitors have to look forward to in the future. Info: (305) 664-9737; www.divingmuseum.org
No matter when you visit Key West, you will have a great time. Not looking for an organized event? Just want to relax, enjoy the tropical vibes, a gorgeous sunset? The month of June is still an amazing time to visit. Spend time at Smather’s Beach, or simply enjoy some live music on Duval.
