Three Perfect Days on Anna Maria Island

Summer’s final long Labor Day weekend is in our sights. What will you do with your three days of Labor Day relaxation in Tampa Bay? Labor Day celebrations are a great final summer blowout for some (if only that meant the end of the heat and humidity!), and whether you are looking for a relaxing weekend to reconnect with your love, or a last hoorah for the summer, we’ve got you covered!

Check out our full guide to Labor Day Weekend in Tampa Bay, from lazy weekend ideas to activities and long weekend events.  And for family friendly things to do in Tampa Bay check out our sister publication, Tampa Bay Parenting.

Updated August 2023, by Zoë Joiner.




Hit the Beach this Labor Day

The gulf waters may not exactly be refreshing in the dead of summer…but if you just can’t resist the call of the sea, head to the coast for a lazy beach Labor Day in Clearwater, St. Pete or beyond. It just doesn’t get more summery than a beach day, especially during Labor Day weekend.

Arrive early to stake out your spot in the sand, complete with snacks and drinks.

These Tampa Bay beaches allow drinking on the beach. Just remember – no glass bottles.

Clearwater Beach


Double check any notices about red tide at online resources like and reports from the Florida Fish and Wildlife Conservation Commission.

Labor Day Lounging by a Tampa Bay Pool

Treat yourself to an indulgent pool day on Labor Day to celebrate the long weekend. You can book a day pass for just the pool through sites like ResortPass.

Participating hotels include Clearwater’s Hyatt Regency Clearwater Beach, St. Pete’s The Don CeSar, and more. Although beware, day passes can be extremely hard to come by on holiday weekends (…like Labor Day), especially in the summertime. Extend your stay by booking a staycation at a local resort with a sweet Tampa Bay pool.

Here are our favorite Tampa Bay hotel pools, including options for day use and those exclusive to overnight guests.

Summer Date Labor Day Tampa Bay
Image credit: Hyatt Regency Clearwater Beach


Go Tubing this Labor Day

Nothing says lazy Labor Day quite like floating down a lazy river or natural spring in an inner tube. If you don’t mind a bit of a drive, these tubing spots are 2 hours or less from Tampa, and the cool water temperatures will provide a welcome reprieve from our steamy summer temperatures.

Make sure to plan ahead though, as parks typically reach capacity early in the peak summer months.

Book a Labor Day Weekend Getaway!

Use the extra day off of work to plan a long Labor Day weekend getaway or staycation. We’ve curated a handful of three-day getaway itineraries for you. Each itinerary includes options for where to stay, where to dine, and fun activities to enjoy in the area this Labor Day. Or, take advantage of one of these summertime staycation deals.

Enjoy a spark-tacular weekend Gulf front at TradeWinds Island Resorts with sand between your toes and a cocktail in your hand, as well as activities galore, such as beachfront cornhole, poolside games, and thrill-seeking rides. Not to mention live music all weekend, daily Vibe pool parties, beach volleyball, food and drink specials, and more – everything you need to stay lit all weekend long!

Celebrate Florida’s endless summer with fireworks on the beach Sunday, Sept. 3 at dusk.

TradeWinds Island Resorts

Have a Labor Day Picnic Date

Grilling is fun, but having someone else do all the work including setup is better. Several local picnic companies offer elaborate setups in local parks complete with fancy cheese and charcuterie spreads and photo-worthy decor.

St. Pete Picnic Co. offers a special package at Sunken Gardens (along with many other local spots). We also like The Picnic Social. Check out our guide: How to Plan a Romantic Tampa Bay Picnic for Two for even more inspiration.

French date night in Tampa - Picnic at Sunken Gardens Labor Day
Image credit: St. Pete Picnic Co.


See a Movie at the Drive-In

How about watching a movie under the stars (…minimal effort required) this Labor Day weekend in Tampa? Drive-in movie theaters near Tampa Bay are romantic and budget-friendly.

Pack snacks and snuggle up for a nostalgic date. Lots of drive in movie theaters are operating in and around Tampa Bay this Labor Day weekend, with just a bit of a drive to places like Funlan, Ruskin Family Drive-In, and Silver Moon Drive-In.


Go on a Sunset Boat Tour

Labor Day weekend booze cruise with sunset views…sign us up! Our favorite sunset tours and cruises range from dinner cruises to dolphin watching and kayaking. But our personal favorite is Florida Tiki Tours, which offers private group tours for 4-6 people on a floating tiki.

Tours depart from Maderia Beach. Cruisin’ Tikis Tampa also offers a similar experience at multiple locations, including one departing from the Tampa Riverwalk.

Labor Day booze cruise tampa
Image credit: Florida Tiki Tours


Plan a relaxing spa day

Use your extra day this Labor Day weekend to really relax and unwind at a local spa. Spas like Pallavi Spa located at the Wyndham Grand Hotel on Clearwater Beach, Spa Evangeline, and Spa Jardin all offer unique treatment options for couples. Refer to our post on Tampa Bay spas for couples for more ideas and treatment highlights.

Labor Day Weekend Activity Ideas

1. Go ziplining in Tampa Bay

2. Visit a Farmers Market (try the Ybor City Saturday Market or one of these other local farmers markets) this Labor Day weekend

3. Unwind this Labor Day at a Tampa Bay rooftop bar or tiki bar


Image credit: Sal y Mar


4. Visit Bok Tower Gardens on a date day trip this Labor Day

5. Go bioluminescent kayaking after sunset

6. Rent bikes and explore one of these local bike trails over Labor Day weekend

7. Savor a lazy Labor Day weekend brunch

Image credit: Élevage


8. Plan a Labor Day staycation

9. Learn new skills during a cooking class

10. Take advantage of some great Florida Resident deals on hotels, theme park tickets, and more this Labor Day Weekend.

11. Spend the day along the Tampa Riverwalk.

12. Take a Labor Day trip to Weeki Wachee Springs or go kayaking around Tampa Bay.


Day Trip to Weeki Wachee Springs State Park
Weeki Wachee Springs State Park


Labor Day Weekend in Tampa Events


Busch Gardens Bier Fest
July 21 – Sept 4, 2023
Busch Gardens Tampa Bay
Each weekend, park guests can toast delicious brews and coast on epic thrill rides at Busch Gardens’ beer-inspired food festival.
Included with theme park admission, weekends only

Florida’s Largest Home Show
Friday, Sept. 1st – Monday, Sept. 4th
Florida State Fairgrounds
FREE Admission on Friday, September 2. $8 adults and $7 first responders Saturday- Monday.

St. Pete Shuffle Friday Nights
Friday, September 1, 7-10pm
St. Pete Shuffle
Learn to play shuffleboard with help from St. Pete Shuffle’s staff and volunteers, who will get you set up on a court and teach you how to play.
$10; free for members and their guests

Image credit: St. Pete Shuffle


Urban Kai Sunset Paddle Happy Hour
Friday, September 1, 6pm
Departing from Armature Works
Enjoy discounted Happy Hour pricing on Fridays for SUP and kayak rentals to take in the sunset on the Hillsborough River this Labor Day!

Y2K Party
Friday, September 1, 8pm
The Orpheum
Don’t miss the ultimate 2000s throwbacks dance party! A DJ will be spinning all your favorites from the 2000s to create a night full of nostalgia that will transport you back to the time of Motorola Razrs, Juicy Couture tracksuits, and Von Dutch hats!
$15 advance sales; 18+

St. Pete Labor Day Mural Tour by Bike
Saturday, September 2, 10am
Tour departs near Florida CraftArt
Hop on your bike or take advantage of Coast Bike Share for a leisurely ride with numerous stops. Learn more about these dynamic murals and the power of public art in St. Pete! Bike rental included.

Sneaker Con
Saturday, September 2, 12 – 7pm
Tampa Convention Center

Sneaker enthusiasts won’t want to miss “The Greatest Sneaker Show On Earth”! Featuring the largest collection of sneakers in the world!  Attendees are encouraged to bring as many shoes as they can carry for selling and trading, and to take advantage of the Authentication services offered By eBay Sneakers.

Culture & Community Fest
Saturday, September 2, 10am – 5pm
Tampa Premium Outlets, Lutz
Head to Tampa Premium Outlets for a day filled with music, food & festivities. Featuring local vendors and health screenings, enjoy a day out shopping with family and friends while enjoying good music and good times. Register on Eventbrite to be entered into the Early Bird Raffle.

L8 NIGHT Saturdays
Saturday, September 2, 11:30pm – 3am
The Floridian Social
Head over to the Floridian Social in St. Pete for their Saturday late night party featuring no cover and drink specials from 11 PM til close. Party with your favorite person in the esteemed live music and craft cocktail venue which used to be an office, movie theater and even a bank.

Hyde Park Village Fresh Market
Sunday September 3rd, 10am – 3pm
Hyde Park Village, 1509 Swann Ave
The perfect South Tampa setting for a stroll, peruse the wonderful, pet-friendly market featuring 80+ local vendors every first Sunday of the month. Shop for produce, handcrafted goods, plants and more. While you shop and stroll, enjoy live music by Gasparilla Music in Village Circle.

Vintage + Makers Market
Sunday September 3rd, 4 – 9pm 
The Orpheum
Peruse over 30 unique vendors, including Fine Art, gifts, jewelry, vintage clothing and handmade goods within the comfortable A/C of The Orpheum in Ybor City!

GeckoFest 2023 – Around the World in 80 Gecko’s – First Friday Art Walk in Gulfport
Saturday, September 2, 10am – 10pm
Downtown Gulfport
Honoring this waterfront village’s unofficial mascot and favorite reptile, the Gecko! This year’s theme, chosen by public voting on the Gecko Ball Facebook page, is “Around the World in 80 Geckos”! The theme offers inspiration for a wide array of costumes, as well as music, dancing, food and drink. Festival-goers are always encouraged to arrive in costume.
Parking and admission to GeckoFest is complimentary and the event is pet and family-friendly.
Great chance to for a Gulfport Labor Day trip!
FREE Admission

Labor Day Food Truck Festival
Sunday, September 3, 12pm – 6pm
The Cuban Club
This food truck festival is an electrifying extravaganza that brings together a diverse range of mobile kitchens and vendors down to Ybor City. Imagine a lively courtyard filled with mouthwatering aromas, vendors, and upbeat music. As you join the vibrant crowd, you’ll find yourself surrounded by people visiting all the vendors and eating some great food.

September Sing-Along Sundays: The Greatest Showman
Sunday, September 3, 3pm
The Tampa Theatre
Come add your lovely voice to the fantastic songs onscreen with Sing-Along The Greatest Showman, the most widely-requested sing-along in Tampa Theatre history! Hugh Jackman plays P.T. Barnum in The Greatest Showman, the 2017 musical celebration of the life of one of America’s true original entertainment pioneers, the producer of the most famous touring circus in history, and the spiritual godfather of marketing.
$14.50, General Admission, or $11.50 for Tampa

Beso del SolTheatre Members

Sunday, September 3, 3pm
Hotel Alba Tampa, Tapestry Collection by Hilton
Don’t miss Tampa Bay’s Premium Latin Dance Pool Party at the beautiful Hotel Alba where drink specials and entrees will be available all day! Dance to all your favorite Bachata, Salsa Romantica, Mambo and more!
$14 in advance; $16 the day of

Downtown Concert at Rock the Park
Thursday, September 7, 6:30pm
Curtis Hixon Waterfront Park
This free monthly music series showcases musical talents of all genres. A perfect way to extend your Labor Day weekend and keep the good vibes flowing through the week.
FREE admission

Tampa Picnics
Photo Credit: Curtis Hixon Waterfront Park

Planning a weekend escape? Check out our guide to spending Labor Day Weekend 2023 in Orlando.


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