July 4th – Fireworks Shows There are four major fireworks shows in the Keys. The Upper Keys show, off Blackwater Sound, is set to start at 10 p.m., and the best seating can be found at Sundowners, Senior Frijoles restaurants, Carribbean Club, and the Marriot Key Largo Bay resort. The show in Marathon is staged off Sombrero Beach. Middle Key residents make a day of it at the beach with games for kids, music, and vendors selling food and beverages. The Lower Keys is at the Big Pine Key Community Park with sky lighting up about 9 p.m. No pets, coolers or personal fireworks allowed. In Key West, viewers stake out positions on the southwest corner of the island. Best viewing and paid picnic is at Casa Marina Resort. July 12th— Underwater Music Festival The 30th annual Underwater Music Festival at Looe Key features waterproof speakers, maritime-themed tunes, divers in costume and more. The special speakers are suspended beneath boats above the reef. The music is simulcast on speakers suspended under boats and over the reef. The event is simulcast on a local radio station. July 17th/ August 21st – Morada Way Arts & Cultural District presents: Third Thursday Art Walk Located between MM 81 and 81 in addition to individual artists, the Red Bone Gallery, Gallery Morada, Pasta Pantaleo Signature Gallery, and Bluewater Potters will be showcasing their work. Admission is free, and the Art Walk is held the third Thursday of each month.
July 19th — Hemingway 5K and Paddleboard Race Folks love this event because it’s an either/or/both event. The paddle race starts at 6 p.m. from the Southernmost Beach in Key West and covers a 3-mile openwater course. The run starts at 7:30 p.m. (a blessedly good idea in the squelching heat of Keys summer) and takes racers through Old Town, including a pass of the Ernest Hemingway Home and Museum. July 30-31 — Lobster Mini Season This is the unfettered pleasure of hunting food (lobser) in crystal blue water and then taking it home and eating, preferably drenched in butter. The sport season starts at 12:01 a.m. on Wednesday morning and lasts through midnight on Thursdays. Typically, extended families from around Florida rent out every single vacation home, bring the kids and grandma, the boat, coolers and other toys. TBD — Christmas and New Year’s in July For a truly local event, we recommend participating in Christmas and New Year’s in July. It’s an annual tradition at the Brass Monkey Bar & Lounge in Marathon (the best little dive bar in Florida) and the two parties bracket the lobster sport mini-season. Best to arrive a little sauced and develop amnesia through the course of the evening. Some things cannot be unseen, but it’s a can’t-miss party.
Sept. 6th — Key Largo to Key West Cycle Challenge This event begins in Key Largo and ends in Key West, 100 cool miles. Participants can enter as a solo rider, a 2-person team or a 4-person team. Groups are required to have their own support vehicles, repair ability, etc. Racers check in at various points to win awards, bragging rights and receive braggadocious finishing medals. The course is mostly on a bike trail (80 miles) that hops across the most scenic highway at different points. Sept. 13th — Lionfish Derby in Key Largo (REEF (Reef Enviornmental Education Foundation) is sponsoring the fifth annual Lionfish Derby in Key Largo on Sept. 13th. Teams of divers compete to see who can bring in the most lionfish, the largest, etc. Team captains must attend a mandatory meeting. At John Pennekamp State Park the day before. Weigh-in is at 5 p.m., followed by scoring, demonstrations and lionfish tastings. www.reef.org Sept. 18-21 — Phil Peterson Key West Poker Run About 10,000 bikers will rumble from Miami to Key West for the annual Phil Peterson poker run. Participants play a hand of cards at various stops along the way and end in Key West where they congregate on Duval Street. The event is a boost during the slow summer months for the Keys economy, plus it raises tons of funds for charities such as the Diabetes Research Foundation and the Key West Sunrise Rotary. Sept. 20th — 2nd Annual Alligator Reef Lighthouse Swim Already 60 people have signed up for the second annual swim to a landmark lighthouse located roughly four miles offshore, though with the tide it feels more like 12 miles roundtrip. Swimmers can enter individually or as teams and are accompanied by support boats or kayaks. It crosses some of the loveliest underwater terrain in the world, not to mention swimming around the pilings of a 141-year old navigation structure. Caution: jellyfish (some years). Sing up: swimalligatorlight.com.