Our Most Favorite Florida Events in May 2023 (That We Think You’ll Love!)

Just call us the party state because we have so many amazing Florida events in May this year! While we’re typically known for sunshine and spring break, we’re also pretty great at hosting spectacular festivals. (Not to brag or anything.)

With so many annual events in Florida, there’s truly something for everyone to enjoy. Over a dozen of these festivals are happening in May alone, and we say there’s no time like the present to start having fun!

Whether you’re a foodie, a music lover, or an adventurer, there’s a May festival with your name on it. (Plus, with some festivals offering free admission, they’re also budget-friendly!) Come on, let’s check them out!

Florida Events in May

These festivals are pretty a-may-zing, but don’t just take our word for it! Take a festival road trip and join in on a soiree everywhere you go!

1. Key West Songwriters Festival, Key West, 5/3 – 5/7

The 27th annual Key West Songwriters Festival is a celebration of up-and-coming musical talent. A hub for country artists who’ve made it big, this festival is five nights of great tunes, good stories, and just appreciating music, no matter how long you’ve been enjoying it or performing it. The largest festival of its kind, KWSF is a must for anyone who likes blaring Randy Houser songs on the radio.

2. St. Augustine Food and Wine Festival, St. Augustine, 5/3 – 5/7

Culinary connoisseurs note that the St. Augustine Food and Wine Festival offers first-class food in the nation’s oldest city! Enjoy the offerings of celebrity guest chefs and celebrity winemakers, all while drinking in the ambiance of this beautiful city.

3. Treasure Coast Seafood Festival, Vero Beach, 5/6 – 5/7

If you couldn’t tell, we think food is something worth celebrating! And the Treasure Coast Seafood Festival highlights the best of Florida fare: lobster, shrimp, fish, and “almost every kind of seafood imaginable.” Everything’s on the table here! While seafood is the star of this show, there will also be arts and crafts, live music, and a kids’ zone.

4. Bacon, Bourbon, and Blues, Oviedo, 5/7

You had us at “bacon.” Bacon, Bourbon, and Blues is a festival of food sampling and bourbon sipping, all to the tune of live music. Due to the drinks on tap, this festival is for folks 21 and older. But if you’re just in it for the bacon (and bacon-infused bites), it’s worth noting they offer non-alcoholic beverages, too!

5. Drake’s Raid, St. Augustine, 5/13

St. Augustine has a fascinating history filled with swashbuckling pirates, and Drake’s Raid recaptures those olden days in all of their glory! Throughout the day you can explore the military encampment, then in the evening, witness the riveting reenactment of the sacking and burning of St. Augustine! (This is one of the best festivals in Florida for our fellow history nerds.)

6. Vero Beach Seafood Festival, Vero Beach, 5/13 – 5/14

We can’t resist good seafood, and that’s why we love the Vero Beach Seafood Festival. (We also love that parking and admission are FREE!) Enjoy fresh seafood (and “land food”), libations, live music, live mermaids, and a kids’ zone!

7. Wesley Well Farms Tomato Festival, St. Augustine, 5/13 – 5/14

John Denver once sang, “There’s only two things that money can’t buy, and that’s true love and homegrown tomatoes!” Thankfully, you can find bushels of homegrown tomatoes at the Wesley Well Farms Tomato Festival! With tomato-inspired dishes, food trucks, farmer meet and greets, and a delicious salsa-tasting contest, you’ll find your inner green thumb feeling truly inspired! Oh, and did we mention there will be adorable farm animals?? We can’t wait for this Florida festival!

8. Welcome to Rockville, Daytona Beach, 5/18 – 5/21

One of the most popular events in Florida, Welcome to Rockville takes place at the Daytona International Speedway and sees attendance rates of around 100,000 people! This jam-packed music festival invites your favorite musicians to take the stage and invites you to take part in this one-of-a-kind rock ‘n’ roll concert! With about two dozen different popular bands every night, it’s impossible not to feel pumped up!

9. Billy Bowlegs Pirate Festival, Fort Walton Beach, 5/19 – 5/20

Join the venerable Krewe of Bowlegs during the Billy Bowlegs Pirate Festival! This pirate party is sure to please with its swashbuckling skirmishes, a tantalizing treasure hunt, and a plunderin’ parade through town!

10. New Smyrna Beach Jazz Festival, New Smyrna Beach, 5/19 – 5/21

The New Smyrna Beach Jazz Festival will soothe your soul with snazzy serenades. A variety of jazz bands will be performing throughout the three-day soiree, and most of the events have FREE admission! Now that’s music to our ears!

11. Tupelo Honey Festival, Wewahitchka, 5/20

You might be surprised to see the Tupelo Honey Festival on a list of Florida events and festivals, but it doesn’t actually have anything to do with Tupelo, Mississippi! We’re buzzin’ about tupelo honey – a delicacy produced when bees use nectar from the blossoms of the tupelo trees that grow in Florida and Georgia wetlands. Enjoy the taste of this rare honey and get a jar to take back home at this fun festival! Other foods, music, and activities for kiddos will also be available!

12. Florida Folk Festival, White Springs, 5/26 – 5/28

One of the most popular Florida festivals in May, the Florida Folk Festival has been going strong for 71 years and is one of the best annual events in Florida. A celebration of all things Sunshine State, you can enjoy over 300 performances of live music, dance, and storytelling that pay homage to Florida’s heritage. Enjoy interactive exhibits with hands-on crafts and music lessons, or indulge in shrimp gumbo, cornbread, and root beer floats!

13. Palatka Blue Crab Festival, Palatka, 5/26 – 5/28

 “Get ready for a pinch of Palatka” at the Blue Crab Festival! This family-friendly shindig features national headliners, concerts, food trucks, and tons of fun for the kiddos in the kids’ zone. The classic Blue Crab Festival is sure to make your Memorial Day weekend a snappy one!

14. Sunset Music Festival, Tampa, 5/27 – 5/28

Celebrating sunsets is kind of a Florida thing, and Tampa’s Sunset Music Festival is the most boppin’ way to do that. Featuring an extensive line-up of musicians, you’ll get to hear a cross-section of genres from techno to trance. Heavy on the electronics, this music fest is all about sensational audio-visual experiences! It’s also one of the wilder festivals and can only be attended by those 18 and older.

15. Jacksonville Jazz Festival

Jacksonville, 5/25 – 5/28

The Jacksonville Jazz Festival is three full days of groovy tunes, food, drinks, and mingling with the music-loving community. The best part about diggin’ the beats downtown is that this live entertainment is free to enjoy!

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There’s something so charming about the experience of local flavors, history, and music, and joining in on one (or more!) of these May festivals is such a fun way to do that! We hope to see you around!

Have you been to any of these festivals? Tell us about your experience in the comments below!

Featured photo: halfpoint via Canva.com