Exciting Weekend Ahead: Competitions, Crawls, and Fireworks in SWFL!

27421 Old 41 Road, Bonita Springs, FL - As summer rolls into full swing across Southwest Florida, there’s no shortage of exciting happenings and events that promise fun for everyone. Whether you’re a fan of music, tattoos, or local flavors, this weekend has something just for you.

The much-anticipated Florida Gulf Coast Tattoo Expo is set to take over the Caloosa Sound Convention Center from June 27-29, 2025. With more than 200 tattoo artists showcasing their skills, alongside live music and food vendors, this expo is not just an event—it’s an experience. Tickets range from $20 to $30, and weekend passes are available for those who want to dive into everything tattoo-related.

Local Talent Takes Center Stage

For those who prefer a different kind of weekend entertainment, Sugarshack Downtown is kicking off its inaugural Downtown Showdown competition on July 1, 2025. This singing contest aims to spotlight local talent from Southwest Florida and will run every Tuesday through August 12. Contestants of all ages are welcome to participate, though parental consent is required for those under 18.

To compete, aspiring singers must upload audition videos to platforms like Instagram, YouTube, or Vimeo and submit their entries through the Sugarshack Downtown website. The competition includes preliminary rounds where eight contestants will perform each week, with the top two from each heat advancing to the semi-finals on August 5. It culminates in a grand final showdown on August 12 for a chance at the grand prize of $2,500!

It’s not just the participants who get a taste of the excitement. The audience plays a role in the judging alongside a rotating panel of local celebrities. This unique competition showcases both talent and community spirit, creating an engaging atmosphere with live music from the Sugarshack Allstars.

More Weekend Fun Awaits

However, the fun doesn’t stop there. On June 28, you can indulge in the Red, White & Booze Pub Crawl in Downtown Cape Coral. Running from 7 to 11 p.m., this lively event aims to take participants to 11 bars and restaurants via limo buses, offering samples of drinks and appetizers for an admission fee of $20 to $30.

Sports enthusiasts can look forward to the Fort Myers Roller Derby Home Game at the Fort Myers Skatium, while fans of theater might enjoy Theatre Conspiracy’s “Funny: Power Plays” at Off Broadway Palm, happening the same weekend. And, music lovers won’t want to miss Johnny Rogers‘ “The History of Rock ‘N Roll Show” at the Arts Bonita Center for Performing Arts.

As you gear up for the weekend, be sure to check the full schedule of events, including popular options like the SWFL Sports Card Show on June 29, or the very special upcoming art showcase, Family Connections: An Inclusive Art Showcase, which opens on July 3, featuring art by students on the autism spectrum.

This weekend is shaping up to be a delight for Southwest Florida residents and visitors alike. With no shortage of activities that range from the entertaining to the artistic, you’re bound to find something that piques your interest. So grab your friends and family, and prepare for a weekend of local flavor and fun!