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Top 10 Summer Events in Key West

25 May 2022
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Fun in The Sun

With the unofficial start to summer just around the corner, it's time to start preparing for summer fun and all the things you will do. As you start planning your Key West vacation, there is a wide range of fun events to look forward to all summer long so no matter when you come, you'll be able to enjoy Key West community at its finest. From kicking off the summer with one of the nation's best pride festivals to celebrations of the food & drinks that make Key West special.

Make sure to book your Key West Florida vacation rentals on the beach as the anticipation builds for so many reasons to gather and celebrate life. There is definitely a lot to look forward to in 2022, so here are the top 10 summer events in Key West. 

key west pride

1. Key West Pride 2022: June 1-5, 2022

One of the largest and most popular Pride festivals in the United States, Key West Pride is guaranteed to be a great time for anyone and everyone. Enjoy spectacular events during this 5-day event full of vibrant energy and fun. The history of the LGBTQ+ community in Key West dates back to the 1940s with Tennessee Williams establishing it as an official gay vacation destination. All the more reason to come celebrate Pride and enjoy a lovely vacation at the same time!

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2. Key West Mango Fest: June 23-26, 2022

This free celebration is about all things mango. Learn mangoes from a wide variety of vendors and still enjoy a relaxing vacation in Key West. This event is one of the largest fundraisers for the Police Athletic League that helps kids get involved in sports and educational programs to give kids a safe place to succeed. 

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3. Key Lime Festival: June 30 - July 4, 2022

What could be more indulgent than celebrating a delicious dessert and all the things that make Key West unique? This eccentric festival is one of the most popular events in Key West with so many different ways to enjoy amazing Key Lime Pie including a pie eating contest. Think you got what it takes? Start planning your trip now!

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4. 46th Annual Swim Around Key West: July 2, 2022

Training for a triathalon? Just love to be in the water? The Annual Swim Around Key West is the only sancitoned, insured, and Coast Guard-approved race around Key West. Swim 12.5 miles in the warm water around Key West that goes through the Gulf of Mexico and the Atlantic Ocean. Sign up today!

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5. Del Brown Permit Tournament: July 10-13, 2022

Whether you're a fly fishing pro or you're just fascinated by how in the world they do it, the Del Brown Permit Tournament is a fun event celebrating a legend. Del Brown made fishing for permit with a fly rod famous in Key West and this event brings the best of the best. If you're planning on entering or you just enjoy good sport, this event is a great one to reel in while in Key West.

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6. Key West Marlin Tournament: July 20-23, 2022

Speaking of reeling them in, the Key West Marlin Tournament really ramps up the competition with one of the hardest fishing challenges in the Keys. Featuring $50,000 in guaranteed cash prizes, you can try your hand at the big one or just enjoy the festivities after the captains bring their catches back to shore.

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7. Sloppy Joe's 41st Annual Hemingway Days: July 21-23, 2022

The 41st Annual Hemingway Look-a-Like contest hosted by Sloppy Joe's is a great way to enjoy the rich history of the island with some laughs. Ernest Hemingway wrote several of his novels during his time in Key West so you can celebrate one of the legendary residents of Key West and enjoy the culture of the island that makes it such a fun place to vacation. This event coincides with the Marlin Tournament celebrating Hemingway's love of deep-sea angling and a wacky "Running of the Bulls" to celebrate his sporting interest.

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8. Key West Tropical Heat: August 10-14, 2022

It's already hot in Key West but add in a festival celebrating gay men 21 & up and the heat really cranks up. Tropical Heat is a 5-day festival featuring many hot events, clothing optional gatherings, and adult-oriented fun. You'll never forget the memories made during Tropical Heat with a ton of hot guys. Start planning your trip today!

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9. Key West Lobsterfest: August 11-14, 2022

The opening of lobster season means one of the best festivals in Key West: Lobsterfest. This is the 25th year for the celebration with so many amazing creations featuring lobster and other delicious, creative foods. Come enjoy the best seafood the ocean has to offer during this year's Lobsterfest. 

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10. Key West Brewfest 2022: September 1-5, 2022

As Labor Day marks the end of summer, Key West Brewfest is a great way to cool off in the Florida sun because it's always summer here. Try more than 150 beers with beer brunches, happy hours, pool parties, and so much more. Brewfest is perfect for those looking to enjoy a summer vacation later in the season with less crowds to compete with. Grab your glass and plan your vacation today!

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Get Ready for Key West Fun All Summer Long and Book Your Key West Vacation Rental Today!

Historic Hideaways offers many amazing Key West vacation home rentals in that place your right in the heart of the action. From large homes for a group traveling together to cozy cottages, you can find the perfect vacation rental for your Key West vacation. If you want to take an extended vacation, monthly rentals are also available. Browse through the many available vacation rentals and book your Key West stay today.

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