From Key Largo to Key West
Summer in the Florida Keys is more than just beautiful water and long days—it’s a season filled with events that bring the islands to life.
From high-energy fishing tournaments in Key Largo to iconic celebrations in Key West, each part of the Keys offers something unique throughout the summer months.
Whether you’re planning your trip around a specific event or simply want to experience what’s happening while you’re here, this guide highlights some of the most notable events across the Florida Keys.
May Events in the Florida Keys
May kicks off the summer season with a mix of sport, endurance, and on-the-water experiences.
The Marathon Bull & Cow Dolphin Tournament (May 1–3) is one of the most popular fishing tournaments in the Keys, drawing anglers from across the region with major cash prizes and a lively marina atmosphere.
On May 9, the Key West Paddle Classic welcomes both seasoned competitors and first-time participants for a memorable day on the water, offering a rewarding course and a strong sense of community.
Later in the month, the KEYS100 Ultramarathon (May 16–17) challenges endurance athletes with a breathtaking course stretching from Key Largo to Key West, finishing near the shoreline at Higgs Beach.
Rounding out the month, the Skippers Dolphin Tournament in Key Largo (May 29–31) brings together anglers for a competitive and social event with over $60,000 in prizes.
May is an ideal time to visit for those looking to experience the active, outdoor side of the Florida Keys before peak summer arrives.
June Events & Celebrations
June brings vibrant celebrations and unique experiences throughout the Keys.
Key West Pride (June 3–7) transforms the island into a colorful celebration of diversity and community, with a full schedule of events including pool parties, performances, and a lively parade along Duval Street.
Coralpalooza (June 4–6) offers a more hands-on experience, inviting participants to take part in coral reef restoration efforts while learning about marine conservation.
The Summer Solstice Celebration (June 8–21) takes place nightly at Mallory Square, where live performances, artisan demonstrations, and interactive experiences create a festive waterfront atmosphere leading up to the longest day of the year.
Mid-month, the Swim Around Key West (June 12–14) challenges participants with a 12.5-mile open-water swim, accompanied by additional events celebrating ocean adventure and endurance.
June blends energy, culture, and meaningful experiences that are uniquely tied to the Florida Keys.
July Highlights
July is one of the most popular times to visit, bringing holiday celebrations and signature Keys experiences.
Fourth of July celebrations take place throughout the Keys, with fireworks lighting up the sky in Key Largo, Islamorada, and beyond. Fireworks over Blackwater Sound are a highlight in the Upper Keys, drawing both locals and visitors to waterfront viewing spots.
The Underwater Music Festival, typically held in early July at Looe Key Reef, offers a uniquely Keys experience where music is broadcast underwater for snorkelers and divers.
Later in the month, Lobster Mini-Season becomes one of the most anticipated events of the year. During this two-day recreational season, visitors and locals head out on the water to catch spiny lobster, creating a lively and social atmosphere across the Keys.
July is vibrant, high-energy, and best enjoyed with a plan in place.
July is one of the most popular times to visit, bringing holiday celebrations and signature Keys experiences.
Fourth of July celebrations take place throughout the Keys, with fireworks lighting up the sky in Key Largo, Islamorada, and beyond. Fireworks over Blackwater Sound are a highlight in the Upper Keys, drawing both locals and visitors to waterfront viewing spots.
The Underwater Music Festival, typically held in early July at Looe Key Reef, offers a uniquely Keys experience where music is broadcast underwater for snorkelers and divers.
Later in the month, Lobster Mini-Season becomes one of the most anticipated events of the year. During this two-day recreational season, visitors and locals head out on the water to catch spiny lobster, creating a lively and social atmosphere across the Keys.
July is vibrant, high-energy, and best enjoyed with a plan in place.
A Note on the Upper Keys Experience
While Key West hosts many large-scale events, the Upper Keys—Key Largo through Islamorada—offer a more relaxed and experience-driven atmosphere.
Here, your days are often spent on the water at the sandbar, snorkeling at John Pennekamp Coral Reef State Park, or visiting local favorites like Robbie’s to feed the tarpon.
It’s a slower, more private version of the Keys—without missing the experience.
Plan Ahead for the Best Experience
Summer events can shape your entire stay, and planning ahead makes all the difference.
Our local concierge team can assist with coordinating your stay around specific events, booking boat charters and sandbar days, securing dinner reservations during peak weekends, and recommending the right mix of activity and downtime.
Where You Stay Matters
The best summer trips in the Florida Keys are the ones that feel effortless.
Whether you’re returning from a day on the water or heading out for an evening event, your home base should offer the same level of comfort and experience.
At Star Properties Destinations, we focus on creating stays that match the rhythm of the Keys—relaxed, elevated, and thoughtfully planned.
Closing
From fishing tournaments and holiday celebrations to cultural events and ocean experiences, summer in the Florida Keys offers something for every kind of traveler.
With the right planning—and the right place to stay—it becomes more than a trip. It becomes an experience.
Planning your stay? Connect with our team to start creating your Florida Keys experience.
