Hola amigos, it's party time in the Bay! Grab your biggest and best hats (Sombrero or derby) and get ready, because this weekend is going to be lit with things to do in St. Pete and Clearwater. Cinco de Mayo is spicing up all the best Pinellas bars and restaurants in your area, with amazing drink specials (did someone say tequila shot?) and muchas fiestas! If you're feeling like you need a little Jose Cuervo in your life, then check out all the spicy Cinco de Mayo events in St. Pete and Clearwater. And if Mint Juleps are more your style, get down and derby at a Derby Day party you'll never forget! Unless, of course, you have one-too-many cocktails, then you're on you're own. 

Whatever mood you find yourself in this weekend, rest assured there are plenty of insanely awesome things to do in St. Pete and Clearwater to make your fun meter go off the charts!

Bring a Date

First Friday St. Pete

On the first Friday of every month, the heart of downtown becomes St. Pete's biggest block party! The fun starts at 5:30 P.M. and goes until 10 P.M. There will be live music, awesome food trucks, vendors and plenty to drink! 

Central Ave Between 2nd & 3rd St, Saint Petersburg, FL, 33701.

Matroda at Elevate Fridays

Matroda heads to Clearwater Beach to be a part of Shephard's Cinco De Mayo Weekend Party! Grab a dance partner and get ready for a great time! This event is 18 and up.   

619 S Gulfview Blvd, Clearwater Beach, FL, 33767. Phone (727) 442-5107

Derby Day at The Birchwood

It's off to the races for Derby Day at The Canopy! Watch the famous derby, enjoy the Juleps and dress to impress! Best-dressed ladies and gentlemen will win some surprises from Woodford Reserve, so don your fanciest hats and bowties for a great time!

340 Beach Dr NE, St. Petersburg, FL, 33701.

2019 Annual Bike n' Eat St.Pete

Hop on board for this restaurant tour by bike! You'll visit five amazing locally-owned restaurants, where each one will share a sample of their most delicious food and share their inspiration. It's the perfect family fun outing for foodies! Hang out after the tour for a post-ride party with local brews and music.

3169 4th Street North, St. Petersburg, FL, 33704.

Cinco de Mayo Caddy's Gulfport

Celebrate Cinco de Mayo Gulfport style! Caddy's Gulfport will have all the necessary party favors, including food specials, Mariachi music and drink specials (do $3 Jose Cuervo shots and $5 margaritas make you wanna cha-cha)? Grab your favorite sombrero and get to Caddy's! 

3128 Beach Blvd S, Gulfport, FL, 33707. Phone (727) 592-2842

Coming to America Fashion Show

Head out to the 1st annual Coming to America Fashion Show! Expect men and women runway models of all shapes, sizes and ages to grace the stage for a day of entertainment like no other. These models would make Tyra Banks proud! 

11141 US Hwy 19 N, Suites 204-206, Clearwater, FL, 33764. Phone (727) 793-8544


2019 Annual Clearwater Beach Taste Fest

Clearwater Beach will once again host this scrumptious event in iconic Pier 60 Park! Expect tastings from over 30 participating restaurants, wine and craft beer, and live musical entertainment from C'Nergy Band! Gates open at 5:30 P.M. 

Causeway Boulevard, Clearwater, FL, 33767. Phone (727) 461-7732

St. Pete Beach Beer Fest

Join in on this one-of-a-kind craft beer experience, set directly on the beautiful intracoastal waterways of St. Pete Beach. There will be over 100 local craft beers and brewing demonstrations from the Tampa Bay area home-brew clubs. Expect tons of delicious beer choices and food truck munchies to fill your belly! General admission includes a commemorative festival tasting cup and water. 

7701 Boca Ciega Dr, St. Pete Beach, FL, 33706. Phone 7272028045


Iration - Live From Paradise! Summer Tour (2 Nights)

Reggae Rise Up is putting on a great show with Iration! This is a two-day summer tour with Pepper, Fortunate Youth and Katastro. Doors open at 6 P.M. and all ages are welcome. 

16 2nd St. N., St. Petersburg, FL, 33701. Phone 727-565-0550

Indigo Girls in Clearwater, FL

GRAMMY®-Award winning, platinum-selling iconic folk duo, Indigo Girls, return to Ruth Eckerd Hall for the first time since 2013! Show starts at 8 P.M. Get your tickets now! 

1111 N. McMullen Booth Rd., Clearwater FL , 33759. Phone 727-791-7400

The Milk Carton Kids

Two-time GRAMMY® nominated acoustic folk duo, The Milk Carton Kids, make their way to Clearwater for their Capitol Theatre debut! See this folk duo put on a great show! Show starts at 8 P.M.

405 Cleveland Street, Clearwater FL, 33755. Phone 727-791-7400

Paul Oakenfold at Beach House Sunday's

Come see Paul Oakenfold at the largest weekly electronic music event on the Gulf at Shephard's Clearwater! Relax on the private beaches or poolside in a cabana then dance the night away on the tiki stage! This is a 21 and up event. 

619 S Gulfview Blvd, Clearwater Beach, FL, 33767. Phone 727-442-5107

Family Fun

May Day Race 2019

These fun and competitive races will travel through beautiful Clam Bayou on the Skyway Trail and end at the Ceridian campus. Little ones can participate in the Kids Dash for Cash where everyone has a chance to win cash in the fun cash blaster. Kids will run for fun and all will receive a finisher medal!

3201 34th St S, Saint Petersburg, FL, 33711. Phone 7274667173
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