Experience An Unforgettable Key West Labor Day Weekend

Key West Labor Day Weekend

Key West is an ideal location for a summer getaway, and tons of events are planned for the Labor Day holiday weekend if you’re looking for something exciting this year. Whether you’re just coming for a long weekend in Key West or planning a longer stay, there is always island fun for visitors of all ages.

There are so many different festivities planned for Labor Day in the Florida Keys that you won’t have to worry about finding something to enjoy with the family, or a fun experience for an adult-only audience. From live music to beer tastings and strolling through various attractions, there’s something fun for everyone.

Stick around to check out our list of our favorite things to do this Labor Day in the Florida Keys and create the summer getaway experience you deserve.


1) The Ultimate Adventure Awaits You After Dark In Key West

While you’re in Key West for Labor Day weekend, consider visiting us at Key West Paddle for a nighttime experience you won’t soon forget. We offer night kayak tours that take you through the mangrove tunnels and forests of Key West to explore the nocturnal wildlife and marine animals like never before.

Each of our guests will glide along crystal clear waters in their own glass-bottomed, LED-illuminated kayak for an aquatic vantage point you won’t get anywhere else. See tropical fish, sea turtles, and other stunning creatures dart through the water as you embark on an ultimate adventure!

For more information about our tour experiences and what to expect on the water, please visit our website at Key West Paddle.

Night Kayaking In Key West


2) Indulge In The Best Beer In Key West At The Key West Brewfest

If you want to let loose and have some fun during the holiday weekend in the Florida Keys, and you love to sample local beer, then the Key West Brewfest should be a no-brainer for your list of events to visit.

Join the masses for a multi-day event that includes beer pairings, and pool parties, and ends in a massive signature tasting event with more than 150 beers to savor.

The Rotary Club of Key West is hosting this event, which features a wide range of activities taking place at different hotels, restaurants, and bars across the island in celebration of Labor Day.

Key West Brewfest


3) Celebrate Key West’s Favorite Son For Labor Day

Jimmy Buffett has been synonymously associated with Key West for many years for his love of the island and his unforgettable musical career. As one of the newest events in the Florida Keys, the “It’s 5 o’clock Key West” festival celebrates Jimmy Buffett with a second line parade that shuts down Duval Street for the day and has three different stops where you can enjoy a drink or a burger in paradise and remember the exciting like of Mr. Buffett.

You can purchase a Parade Pass for a $30 donation, and all proceeds are distributed to the Bahama Village Music Program. This program works to inspire local young musicians to learn more about their craft and become better musicians and better people without having to worry about paying for instructions. Local young musicians starting at age 6 and up can enjoy free music lessons and more thanks to the help of the Bahama Village Music Program.

The second line parade ends at Truman Waterfront Park where guests can enjoy a free “Friends of Jimmy” live music experience. Stay tuned for more information on the concert experience as new acts and musicians may be added for the Labor Day celebration.

Good to know: If you visit the event you can also enjoy themed events, planned dinners, sailing excursions, tours, and so many more exciting things that celebrate the life and career of Jimmy Buffett.

Live Music Concert - Jimmy Buffett Day In Key West


4) Key West Attractions For Labor Day Thrill Seekers

If you’re a thrill seeker looking for an adrenaline rush during your Labor Day getaway in Key West, you’re in luck! The Florida Keys is one of the best locations in the world for adventure seekers who love catching a thrill on the water! With crystal clear waters and white sand beaches all over the island, there are tons of rental companies and opportunities to find excitement in the sea.

Banana boat rides, jet skis, and parasailing are among some of the most exciting water sports available in Key West, but you can also choose to rent some scuba equipment, kayaks, or paddleboards for a more relaxing day on the water.

Whatever your water sport of choice Key West is the playground for thrill seekers and water lovers. So go ahead and dive in this Labor Day weekend and make some memories that will last a lifetime.

Jet Ski Experience - Key West Labor Day Weekend


5) Everyday Excitement To Discover For Labor Day In Key West

There are an endless number of Key West attractions to choose from for your Labor Day trip this summer, and you don’t have to wait for an event to enjoy them. From sunset sails to museums and aquariums to explore, there’s a never-ending number of things to do.

The Ernest Hemingway House and Museum is perhaps one of the more popular museums on the island and allows you to wander through the home of Ernest Hemingway and see how the iconic figure lived while he was alive in Key West.

Other museums and attractions include:

  • Sails To Rails Museum – Located in the historic Flagler Station, this museum showcases the island’s connection to the railroad and the sea

  • The Key West Aquarium – Enter an underwater world at the Key West Aquarium, one of the oldest aquariums in Florida. See a variety of marine life and get hands-on with sharks, turtles, tropical fish, and stingrays

  • Southernmost Point Buoy – No visit to Key West is complete without a stop at the iconic Southernmost Point Buoy. It has become a popular photo spot for visitors, who line up to capture a picture with this famous landmark

Many of the popular attractions in Key West are located on the Conch Train Tour route, and available on the hop-on-hop-off tour for easy access!

Sunset cruises are also a popular option for visitors in Key West. Join a group of locals and other guests or hire a private charter to head out on the water and enjoy a romantic and relaxing view of the setting sun over the horizon.

If a sunset cruise isn’t your cup of tea, then check out the Sunset Celebration at Mallory Square for an exciting evening of Labor Day fun! The celebration takes place every day at sunset and kicks off with street performers and musicians, and has plenty of street vendors and restaurants around to satisfy your every need during the festivities.

Whether you have the kids in tow or looking for a romantic way to spend your evening with someone special, the celebration at Mallory Square has something for everyone this Labor Day.

Mallory Square Sunset Celebration - Key West Labor Day Weekend


Labor Day Fun Is Easy To Find In Key West

Now that you have an idea of just some of the exciting things you can take part in this Labor Day in Key West, you can start planning the summer trip of a lifetime. Here at Key West Paddle, we pride ourselves on providing every guest with an unforgettable experience on the water.

Climb aboard your very own glass-bottomed kayak to see the marine life glide beneath your vessel in illuminated waters. There’s no better way in Key West to see turtles, colorful fish, and nocturnal life in their natural habitat.

Head to our website to learn more about our tours and to schedule your unforgettable nighttime experience with our expert guides this Labor Day!

1 hour 30 minutes
Group Size
Up to 18

Night Kayak Guided Tour

Get a single or double glass-bottom kayak illuminated with lights and follow our tour guide on this one of a kind, unforgettable and simply magical adventure.

This slow paced, immersive, and very relaxing experience will allow you to see some cool, active at night marine life as you are gliding through crystal clear waters of Key West.

Guests will experience going through narrow mangrove tunnels at night, floating around shallow and calm waters as the tour guide will look for interesting critters for everyone to see.

3 hours
Group Size
1 to 6

Key West Sandbar Trip

Key West sandbars are our local well kept secret. This is where we take our families to hang out and relax on our days off. This is the perk of our island lifestyle. Now we want to share this experience with you.

Turquoise shallow waters, epic picture worthy sights all around you that look like a postcard - that is what you're signing up for!