This Weekends Events: June 27-29, 2025

SWFL Weekender Presents

THIS WEEKS SPONSOR: XV POWERSPORTS

XV Powersports sells new and used Golf Carts, UTV’s, ATV’s and Tractors. Now offering remodeled EZGO Golf Carts starting at $6,899!! Call or Text them today to get started at 239-426-7966.

CALL OR TEXT 239-426-7966

MAIN EVENTS:

CARS ON 1ST (DOWNTOWN FORT MYERS)

Event by CarMeets SWFL

First St, Fort Myers, FL 33902

Start your engines, Fort Myers! The ultimate car show is taking over First Street on June 28th, 2025 from 10AM to 7PM — and it’s going to be WILD!

Cars on 1st brings: Live Performances | DJ Sets | Food | Raffles | Awards | Family Fun | Boxing Exhibition From classics to exotics, we’re shutting down the street from end to end!

This one-day experience showcases a curated lineup of 300 Plus Classic, Muscle, Exotic, and Modified cars displayed along historic First Street, bringing together automotive enthusiasts, local businesses, families, and philanthropists. Attendees enjoy live entertainment, vendor booths, food trucks, VIP experiences, and live boxing demonstrations—creating a unique blend of lifestyle, culture, and community engagement. ​ Cars on First is more than just a car show—it’s a platform to invest in the future of Southwest Florida’s youth.

ARABIAN NIGHTS BAZAAR

Event by Backyard Social

16371 Corporate Commerce Way, Fort Myers, FL, United States, Florida 33913

Shop our outdoor Mystical Night Market

Our curated outdoor market supporting local artisans.

Find boutiques, plants, snacks, coffee, wares & more!

  • Alfi Eyeware

  • Montgomerie Gray

  • Spirit Glow Home

  • FJ Designs by Ange

  • Chasing Bliss Boutique

  • Who Gives A Shirt?

  • Aruba Organics Chimes by Design

  • Charm Bar

  • Crusty Cravings

  • Clothing Bar

  • Charm Bar

  • Sanibel Braids and hair wraps

  • Paws and Pups Boutique

  • D1 Craft Room

  • Drink Specials available! 6 unique food trucks inside. Outdoor games.

COUNTRY NIGHT AT WHISKEY PARK: BULL RIDING + LIVE MUSIC
Event by Whiskey Park

3380 Mercantile Ave, Naples, FL, United States, Florida 34104

Hold my whiskey 🤠

Bull riding. Big Cypress Band. Ten bucks at the door. Country Night goes hard Friday, June 27 from 9 PM-12 AM.

Cape Coral Farmers Market

Event by Chamber of Commerce of Cape Coral

EVERY Saturday 8:00am - 1:00pm

Club Square SE 47th Terrace and SE 10th Place, South Cape

Voted Best of the Cape for Farmers Markets the last 6 years!

Third Street South Farmers Market

Event by City of Naples

245 13th Ave S, Naples, FL 34102

Find the Market in the Neapolitan parking lot between Third Street South and Gordon Drive. Year-round, the Third Street Farmer’s Market is open every Saturday morning from 7:30 until 11:30 a.m!

GROUPER FEST @ Fort Myers Brewing Company

Event by: Fort Myers Brewing Company and Rock Republic

12811 Commerce Lakes Dr, 28, Fort Myers, FL, United States, Florida

Friday, June 27 (2pm-11pm)

Food Trucks: Don’t Give Up, Mambo!, South Pizza Co, The One Stop Food Truck, Wicked Streatery (2pm start for all)

Live Music: No Wrong Turn (3pm), Ben Allen Band (7pm)

Saturday, June 28 (Noon-11pm)

Food Trucks: Blades of Glory, Detour Diner, Let’s Get Nood, Pansardo Italian Deli, Wicked Streatery (12pm start for all)

Live Music: Briz & Lady (12pm), DJ Bigs (3pm) and Rock Republic (7pm)

Sunday, June 29 (Noon-8pm) – Kick the Keg Party/Hangover Party

Food Trucks: Yo Samara’s and Don’t Give Up (12pm start for all)

Live Music: Orlando Phillips (Steel Drums 12pm) and Jenny Ve (3pm)

Plus, FIBB will be on site with a DRIPP IV THERAPY station to get you back on your game! Try the “Myers Cocktail” during the event from 1-5pm on Sunday, June 29th.

FLORIDA GULF COAST TATTOO EXPO 2025

Event by Florida Gulf Coast Tattoo Expo, Inferno Rock Radio, and Country Hits Now

Caloosa Sound Convention Center

The Florida Gulf Coast Tattoo Expo will take place at the 30,000 square foot, recently renovated, Caloosa Sound Convention Center in the Historic River District of Downtown Fort Myers, Florida.

The convention center is perfectly situated next door to the newly built, waterfront host hotel . . . The Luminary. Our official MC, Joey Tattoo, will navigate you through, and to, all the excitement we have to offer up that weekend.

The expo will feature over 250 local, national and international artists tattooing ON-SITE (by walk-up OR by appointment), industry specific vendors, as well as vendors offering jewelry, fashion, oddities, local goods and more!

We will also host daily tattoo contests, headed up by Yall Quinones "Yallzee", along with Alwin Perez and Funhouse Tattoo Owner, Chris Pitre "Casper", LIVE music and entertainment, before hitting downtown and all it has to offer!

Come catch the latest tattoo designs and trends, watch the industry's top artists put in the work, and best yet - get yourself a jaw-dropping, bangin' tattoo!

General admission pricing: Friday $20 - in advance / $25 at the door Saturday $25 - in advance / $30 at the door Sunday $20 - in advance / $25 at the door Weekend Pass $40 - in advance / $45 at the door ​

  • Children 12 and Under are Free

SUNDAY NIGHT TRIVIA- 5 O’CLOCK SOMEWHERE BAR AND GRILL

Event by Compass Hotel Naples FL

4805 Tamiami Trail N, Naples, FL, United States, Florida 34103

Join Us for Trivia Night at 5 o’Clock Somewhere Bar & Grill! Test your knowledge and enjoy some friendly competition every Sunday at 5:30 PM! Hosted by Spotlight Entertainment SWFL, our weekly trivia night is the perfect way to cap off your weekend. 🎉 What to Expect:

• Fun and engaging trivia questions

• Exciting prizes for the winners

• Delicious food and drinks from our menu Bring your friends, form a team, and see if you have what it takes to claim the top spot!

No reservations needed—just show up ready for a great time.

📍 Location: 5 o’Clock Somewhere Bar & Grill Compass Hotel Naples

We can’t wait to see you there! 🌴✨