Celebrate Labor Day In Tampa Bay - Fun-Filled Activities Await

Labor Day In Tampa Bay

From family-friendly activities for parents traveling with kids to action-packed Labor Day weekend fun with friends, there’s never a shortage of Tampa Bay Labor Day events to choose from. You can spend your Labor Day weekend lounging in a cabana on the beach or pick one of the exciting Labor Day events in Tampa to make memorable holiday weekends come to life.

Celebrate Labor Day weekend in Tampa Bay with family or friends and enjoy a wide variety of holiday weekend events and activities perfect for creating lasting vacation memories. The Tampa Bay weather is even sweeter after those peak summer months, and there are enough drink specials to cool you down when those steamy summer temperatures rise. Keep reading to discover our favorite ways to celebrate Labor Day in Tampa Bay!


The Perfect Start To Your Clearwater Labor Day Trip

Whatever brings you to Pinellas County for your Labor Day weekend celebrations, The Tropics Boat Tours wants to help you make the most of your Tampa Bay excursion. We have a variety of tour options that are easily family-friendly and fun for adult groups.

One of our most popular excursions is the dolphin-watching tour. Load up on one of our double-decker boats to cruise through Clearwater Bay and Clearwater Pass to search the waters for the ever-present and playful dolphin. Another cruise option takes you out on the bay to experience the stunning Tampa Bay sunset from an entirely new perspective.

 Be sure to arrive early to your tour to choose your preferred vantage point from the interior cabin or the open-air deck on top. Whichever tour options float your boat, be sure to book early because spaces on each tour fill up quickly.

Dolphin Watching Labor Day At Clearwater Beach


Check Out The Labor Day Party Scene

If you’re fortunate enough to experience Tampa Bay Labor Day events without children in tow, you must see how the area celebrates the late summer holiday. There are tons of locations around Tampa Bay to find a Labor Day weekend party, no matter what your vibe is.

There’s everything from an outdoor cookout-style Labor Day party with a hot dog eating contest and live music to a wild foam party complete with LED and glow giveaways and a professional body painter on deck to help you blend in with the scene. Here are just a few of the locations around Tampa Bay to find a Labor Day party:

  • Aloft Hotel

  • Lucky Lizard Tap House

  • MacDinton’s Irish Pub

  • Bogota Kitchen and Bar

Tambay Bay Hotdog Eating Contest


Lace Up And Join The Fun

Every year Tampa Bay hosts a kickball tournament open to the public. The area is full of enthusiastic competitors, so you’ll either be in for a fight to win or have a thrilling game to keep you entertained for an afternoon of fun in the sun.

Picnicking with loved ones and friends is encouraged, and camping out in the lot for a good old-fashioned tailgate is also a welcome festivity. So pack up the coolers, put your game face on, and see if you will be one of the 20 men or women chosen to represent one of four teams in the Labor Day kickball tournament in Tampa Bay!


Enjoy An Indulgent Pool Day To Beat The Summer Heat

You don’t have to pay resort suite prices to enjoy the perks and luxury of spending a relaxing weekend at one of their pools. You can treat yourself to a high-end poolside experience while still indulging in a lazy Labor Day. Resorts offer day passes and pool passes to visitors, which means you don’t have to pay five-star accommodation prices to enjoy the same amenities.

From poolside food and drink service to shaded cabanas under swaying palm trees, there are many Tampa Bay pools available so that you can lounge in peace during your Labor Day weekend getaway. Check out these hotels and resorts for the best long weekend poolside experience:

  • Compass Hotel Anna Maria Sound by Margaritaville

  • Hyatt Regency Sarasota

  • Don Cesar

  • Sun Outdoors Sarasota

  • Tampa Mariott Water Street

Tamba Bay Pool Day This Long Weekend


Stroll A Scenic Bayshore Boulevard

At least once during your long weekend away in Tampa Bay, you have to experience a leisurely stroll on the most scenic sidewalk in America. Regarded as one of the longest continuous sidewalks in the world, the Bayshore Boulevard offers more than just beautiful scenery.

With its stunning waterfront views and vibrant atmosphere, Bayshore Boulevard is the perfect destination to make the most of this holiday weekend. As you explore, you’ll come across a variety of Labor Day events that will add an extra dose of fun to your long weekend.

Labor Day Weekend Getaway At Bayshore Boulevard


Go Back To Basics For A Simple Labor Day Weekend Beach Day

Clearwater Beach is a wonderful location to enjoy a lazy day with your family or friends on fine sugar-white sand. The beach is beautifully maintained and dotted with swaying palm trees and canopied lounge chairs just begging to help you slip into a peaceful nap under the sun.

Make sure to arrive early enough in the day to snag one of the cabanas or umbrellas along the beach or to find that perfect spot in the sand for your coolers and beach chairs. This is another way to beat the summer heat if you would rather enjoy the cool water temperatures at Clearwater Beach over the warm pool water at surrounding resorts.

Labor Day Holiday At Clearwater Beach


Sign Off On A Romantic Labor Day Weekend With Dinner Cruises

If you’re using your Labor Day weekend for a romantic getaway, then you absolutely have to add a dinner cruise in the waters surrounding Tampa Bay to your list of things to do on date night. No matter where you’re staying in the area, there’s sure to be a boat touring company nearby offering a wonderful seafood meal on the water.

If you time your dinner excursion just right, you just might get to enjoy a glass of champagne or share a cocktail with your sweetheart as the sun goes down over the bay. Check with the concierge at your accommodations to see where the nearest dinner cruise accommodations are during your Labor Day weekend.

Saturday Night Romantic Dinner Cruise


Take In The Best Views Of The Bay For Labor Day

When you want to take in the best sights of Tampa Bay from the vantage point of the open waters of Clearwater Bay, then you have to check out our dolphin watching and sunset celebration tours. Our double-decker boats offer an indoor or outdoor cruising experience and have a full bar on deck for your enjoyment during Labor Day weekend.

Best Views Of Tampa Bay For Labor Day


Head to our website to book your preferred tour experience today to ensure your spot for Labor Day weekend!

1 hour 45 minutes
Group Size
Up to 126

Dolphin Exploration Tours

Our Dolphin Exploration Tours will take you from Clearwater Bay out Clearwater Pass on the beautiful emerald green waters of the Gulf of Mexico (weather permitting) in search of the Sun Coast’s favorite….the Bottlenose Dolphin.

In addition to offering Guaranteed Dolphin Sightings*, your Captain will highlight some fascinating facts about the natural wonders our Gulf Coast offers as well as point out celebrity mansions along the way.

The tour offers something for everyone, including educational information on our area and our wildlife, and optional drink upgrades including unlimited beer and soft drinks for the adults!

Just sit back, relax and enjoy the ride!

2 hours 15 minutes
Group Size
Up to 126

Independence Day Fireworks & Sunset Cruise

This event includes a sunset experience then go towards the Imagine Clearwater Grand Opening celebration for a fireworks experience. Returning approx. 9:45pm. $5.00 drink special. No drink packages will be available.

1 hour 45 minutes
Group Size
Up to 126

Sunset Celebration Cruises

The Tropics Sunset Celebration Cruise will take you from Clearwater Bay through Clearwater Pass to the beautiful Gulf of Mexico (weather permitting).

Sail the beautiful waters of the Gulf of Mexico as you view a breathtaking Florida sunset and — if you’re lucky you may witness the legendary green flash.

Your crew will point out some interesting facts about the natural wonders of the Gulf Coast as well as popular sights along the way. We are pleased to include a Complimentary Sunset Champagne Toast for all guests 21 and up."