Things to Do in Key West with the Family This Summer
Summer in Key West brings more than sunshine and turquoise water—it’s a season packed with family-friendly events for every kind of traveler. At Parrot Key Hotel & Villas, we’re lucky to be surrounded by the very best of it. Whether you're traveling with little ones, teens, or multiple generations, there’s no shortage of things to do together. From pie-eating contests and marlin tournaments to literary tributes and tropical concerts, the island keeps the calendar full and the energy high. Here’s a look at what we’re excited about this summer.
Pucker Up at the Key Lime Festival
July 2–5, 2025 | Various Locations in Key West
The Key Lime Festival is a lively tribute to the citrus that put Key West on the culinary map. Expect everything from lime-themed artwork to creative food and drink events, all focused on Key lime. Families can sign up for a mini pie-making class or cheer on contestants during the dramatic pie drop from the top of the Key West Lighthouse. There’s also a 5K run, a sip-and-stroll for the grownups, and sweet treats around every corner. It’s a flavorful way to kick off July on the island.
Watch Fireworks on Independence Day
July 4, 2025 | Studios of Key West Rooftop, Hugh’s View
Spend the Fourth of July watching the sky light up over the water. Studios of Key West offers a rooftop celebration at Hugh’s View with unbeatable views of the fireworks. Tickets include a drink and music from a live DJ, making it easy to keep the whole group entertained. Wear your red, white, and blue best, and soak in the island atmosphere from above. It’s a fun-filled, memorable way to celebrate the holiday together.
Compete in the Key West Marlin Tournament
July 16–23, 2025 | Stock Island Marina Village, 7005 Shrimp Rd.
Anglers of all ages will be drawn to the thrill of the Key West Marlin Tournament. With $50,000 in guaranteed cash prizes and the legacy of Hemingway in the background, this event combines friendly competition with serious fishing. Teams aim for marlin, spearfish, and other big catches while enjoying time on the water. For families with a passion for sportfishing, this tournament is a summer standout. The setting at Stock Island Marina Village makes it easy to spend the day dockside.
Celebrate Literature at Hemingway Days
July 23–27, 2025 | Various Locations in Key West
Hemingway Days is a weeklong celebration of one of Key West’s most legendary residents. Events honor the author’s work and life with a mix of literary talks, museum exhibits, and active experiences like a 5K run and paddleboard race. There’s something happening every day, making it easy to build a flexible itinerary that fits your family’s pace. Whether you’re a fan of literature or just enjoy a good festival, this one blends culture and fun in true Key West style.
Stop by Sloppy Joe’s 44th Annual Hemingway Look-Alike Contest
July 23–27, 2025 | Sloppy Joe’s Bar, 201 Duval St.
One of the most famous parts of Hemingway Days is the look-alike contest at Sloppy Joe’s, where dozens of “Papas” compete for top honors. Held over three nights, the contest draws big crowds and lots of laughs. It’s a quirky, only-in-Key-West tradition that’s fun for families to watch together. Sloppy Joe’s itself has a long history with Hemingway, adding an extra layer of charm to the scene. The final round on Saturday is always a crowd-pleaser.
Wear Your Pamplona Best at Running of the Bulls
July 26, 2025 | Greene Street, Outside Sloppy Joe’s
The Hemingway Days celebration continues with the Running of the Bulls—Key West style. Expect costumed runners, Hemingway look-alikes, and a parade of handmade “bulls” that are more hilarious than intimidating. This free event is a family favorite, with plenty of photo ops and crowd energy. It’s one of those local traditions that captures the playful spirit of the island. No reservations needed—just show up ready to laugh.
Honor Jimmy Buffett at Just a Few Friends
August 29–September 1, 2025 | Across Key West
As summer winds down, Parrot Heads and island fans gather to celebrate Jimmy Buffett’s legacy. Just a Few Friends is a four-day tribute filled with live music, beach parties, and sunset cruises. The schedule includes performances by musicians who shared the stage with Buffett, along with brunches, film screenings, and a heartfelt memorial parade. It’s a great way to close out the season, especially for families who’ve made Buffett part of their soundtrack over the years. Proceeds benefit local causes, including youth music programs.
At Parrot Key, we love watching guests experience the island’s unique spirit through unforgettable events, from citrusy celebrations to literary tributes. There’s always something happening—whether you're here for a long weekend or a full summer break. We’ll be here when you need a poolside break, a beachside view, or just a place to recharge in between all the fun.