Key West Labor Day Weekend: Plan The Perfect End To Summer

Key West Labor Day Weekend: Plan The Perfect End To Summer

Key West Labor Day Weekend

Are you looking for the perfect place for a Labor Day vacation that will help you hold on to warm weather and sunshine for just a little bit longer? There’s one place where the music, drinks, and good vibes continue to flow long after the last days of summer are checked off from the calendar. Let’s start planning!

A Key West Labor Day weekend is the perfect end to summer! While summer might be winding down in the rest of the country, Labor Day in Key West is a vibrant, festive time that offers all of the sightseeing, nightlife, and beach time that’s associated with peak summer.

Of course, summer weather shows no signs of slowing down just because the weekend marking the official end of summer is here. With average temperatures between 80 and 90 degrees Fahrenheit, the start of September is a wonderful time to visit the Florida Keys if you’re hungry for a truly tropical experience.

How should you spend your long weekend in Key West? This guide covers what you need to plan the ultimate adventure in paradise to close out summer this year!

1) Take A Relaxing Boat Trip In Key West With The Top Charter Company

A private boat tour in the heart of paradise is the ultimate addition to a Key West Labor Day weekend! Did you know that you can hop on a private sandbar tour to beat the crowds? Here at Key West Boat Trips, we offer a number of itineraries that allow our guests to enjoy rare sightseeing experiences that include:

  • Sandbar hopping in Key West
  • Visiting the mangrove trails of Mud Keys
  • Exploring the sandbar at Snipe Point
  • Key West sunset cruises on backcountry waters
  • A Key West dinner or lunch cruise with plenty of time to wade or snorkel in shallow turquoise waters while your fresh lobster is being prepared
  • Snorkeling at Boca Grande Key
  • Electric foil rides around Key West

With our amazing destinations and experienced captains, Key West Boat Trips is the top choice for Key West charters. Our guests love having the ability to take off on private tours to see parts of Key West that most visitors never get to see.

Enjoy our affordable rates and fast bookings to plan your little taste of endless summer in Key West!

Key West Eco Tours - Boat Trips

2) Attend The Jimmy Buffett Memorial Event During Labor Day Weekend In Key West

Jimmy Buffett’s legacy will take over Key West during a city-wide event over Labor Day weekend! From Aug. 29 to Sept. 2, locals and visitors can enjoy a jam-packed schedule that celebrates the feel-good vibes of the place known around the world as the Conch Republic! The event is being called “Just a Few Friends” day in honor of those beloved lyrics sung by Buffett.

This event will feature sailing trips, live performances, themed dinners, and so much more! The highlight is the parade that will move from Duval Street on the main drag in Old Town to Truman Waterfront Park at 5 p.m. on Sept. 1. Attendees can enjoy a free live music concert and festival at the park at the conclusion of the “Second Line” parade. If you’d like to purchase a Parade Pass, the cost will go toward supporting the Bahama Village Music Program and Reef Relief causes that were near and dear to Buffett’s heart!

Don’t miss your chance to spend the holiday weekend taking part in an iconic celebration of the favorite son of the Conch Republic while contributing to a cause that was meant to inspire local young musicians!

Fun fact: Did you know that Aug. 30 is officially Jimmy Buffett Day in Florida? The Florida House of Representatives established the holiday to honor Jimmy Buffett’s love and dedication to Florida.

Acoustic Guitar

3) Attend Key West Brewfest For Drinks, Games, And Fun

While Key West may be synonymous with rum, there’s also a strong beer culture all throughout the Florida Keys. You can get your taste of hops in paradise during Key West BrewFest from Aug. 29 to Sept. 2. Hosted by Southernmost Beach Resort, this multi-day festival offers an action-packed itinerary that includes:

  • Beer pairing dinners
  • Pool parties
  • Tap takeovers
  • Bingo
  • Belly-flop contents
  • Beer tasting with more than 150 beers

While there’s no doubt that this beer tasting festival is one of the top Labor Day events for beverage connoisseurs, Key West BrewFest is also perfect for anyone who wants to attend one of the biggest pool parties on the island!

Tip: If you plan to attend this very popular event, we recommend booking your tickets online long before your arrival date in Key West!

Key West BrewFest - Beer Tastings

4) See The Sunset Celebration At Mallory Square

While the sunset celebration at Key West’s Mallory Square takes place 365 days a year, this is one of those events that feels even more special when it’s Labor Day in Key West!

Show up about an hour before sunset to enjoy live music, performers, and food trucks. The sunset views at Mallory Square have been adored by everyone from Mark Twain to Ernest Hemingway.

Mallory Square Sunset Celebration

5) Enjoy Some Classic Water Sports During Labor Day In The Florida Keys

What’s Labor Day without some water sports? There will be plenty of downtime between Labor Day parades and events to get into the warm waters of the Florida Keys. Here are some suggestions for enjoying quality time with the tides between fun events:

  • Swim at Fort Zachary Taylor – The gorgeous natural beach here is prized for mild currents that are ideal for swimming and snorkeling. If you’re experienced, this beach is also considered one of the best spots in Key West for scuba diving
  • Rent a jet ski or take a guided water excursion
  • Enjoy banana boat rides that offer a fun alternative to tubing
  • Parasailing is an exhilarating experience, allowing you to soar above the crystal-clear waters and take in breathtaking views of the island

Pro tip: Indulge in an unparalleled experience with our illuminated glass bottom kayaks, providing a one-of-a-kind adventure like no other. Experience a truly exceptional night kayaking adventure along the captivating mangrove trails in Key West.

Night Kayaking Tour In Key West

Labor Day Is The Best Time To See Famous Key West Attractions

The energy around Key West during Labor Day weekend is unmatched! Your visit will show you that summer truly is a state of mind.

While Key West comes alive in a big way for Labor Day, the best part is that you won’t have to battle the crowds to have fun here. With most families back in school for the year, the period between the end of August and start of September is much less “touristy” compared to spring break or peak summer.

There’s no need to stay tuned for more information about all the fun events coming to Key West this Labor Day weekend! Get a start on planning the perfect end-of-summer getaway by booking your sunset cruise or sandbar-hopping tour with us. Our experienced team is ready to cater to your every need as you set sail on private charter, swim in crystal-clear waters, hop from golden sandbar to golden sandbar, and snorkel peacefully among sea creatures in the wild.Experience an unforgettable Labor Day getaway by booking with Key West Boat Trips today!

Key West Private Sunset Cruise

Ready for your next adventure?