Sandwiched Between Tampa And Sarasota Is Florida's Underrated Funky City With Waterfront Shops And Food

In the modern world where chain stores and restaurants are prevalent and corporate entities abound, it's refreshing to see a small town that has eschewed big businesses in favor of small, locally-owned enterprises. One Florida town's commitment to retain its eclectic, inclusive flair has drawn visitors, creatives, and retirees alike and built an artsy community that stands out in the state. Gulfport, Florida, is a small waterfront community with a brick main street just 5 miles from the better-known St. Petersburg, a destination with a vibrant downtown and award-winning beaches, but tiny Gulfport holds its own and is worth a visit.

Once inhabited by several Indigenous tribes before it was settled by the Spanish to become a port town-turned-fishing village, then evolved into an attempted retirement community for Civil War veterans, Gulfport finally settled into its modern identity as the "Creative Coast of St. Pete." Downtown is paved with brick streets laid by hand in the 1920s, and it features a historic casino and ballroom acting as a cultural and community center for generations. Gulfport prides itself on its inclusivity, pet-friendly and queer-friendly spaces, thriving art scene, and laid-back vibe, hosting a number of community events including an annual Gecko Fest to celebrate its unofficial mascot, and twice-monthly art walks which encourage vendors, artists, and visitors to come out and immerse themselves in a night market-type experience.

You can fly into the tiny St. Pete-Clearwater airport, about a 20-minute drive from Gulfport (depending on where you're flying from, Allegiant Air has excellent, affordable options through PIE), or Tampa International Airport, a much bigger hub across the causeway on the mainland yet still only about a 30-minute drive from Gulfport. It's also about an hour's drive from Sarasota, another favorite Florida Gulf Coast destination with white sand beaches.

Despite the back-to-back hurricanes in 2024, Gulfport's resilience and community spirit have the city on the road to recovery. The Pinellas County area, including Gulfport, was hit hard, and many local beaches closed for months. While Gulfport's public beach is open, its sand volleyball courts remain closed as of this writing. Gulfport's beach overlooks Boca Ciega Bay and features Williams Fishing Pier, a fenced playground, a pavilion, and restrooms. Clam Bayou Nature Park, a small preserve nearby on Boca Ciega Bay, has abundant wildlife and a boardwalk of hiking trails around its estuary, plus a launch for kayaks and canoes. It's part of the Great Florida Birding Trail, so bring your binoculars!

Stroll the brick streets downtown or take the Gulfport trolley to see quaint cottages and ancient oaks covered in Spanish moss. Parking is free, there are no meters in Gulfport. Start your stroll at Low Tide, a kava bar in the middle of the action with indoor/outdoor seating. Kava is popular throughout Florida — the root-based beverage from the South Pacific is said to have relaxing properties, a total vibe match with Gulfport. Have a grouper BLT and a Painkiller on the waterfront at Stormrunner's Tavern, then pop into boutiques like Sail Market or Bo-Tiki for locally-crafted souvenirs or crystals. Take a beer break at Gulfport Brewing or get kombucha at the Gulfport Corner Store. End with freshly-made Italian at Pia's Trattoria or fine seafood dining at The Pearl (reservations recommended).

Gulfport's a great stopover even if you're using it as a gateway to explore St. Petersburg. With many underrated little Florida beach cities like Madeira Beach, Indian Rocks Beach, and others dotting the Gulf Coast up to Clearwater, there's no shortage of sunny days and great places here.

Gulfport has a unique mantra: "Come here tired and get revived. Come here scorned and be accepted. Come here misunderstood and find others like you. Come here rushed and get laid-back. Come here alone and make friends. Come here happy and stay here happy." To that end, community events and local businesses strive to create inclusive environments that set Gulfport apart.

The Blueberry Patch is a semi-secret venue with an "Art, Love, Music" motto, only open three nights a month for live music and events. The business also hosts weekly volunteer days, pouring back into the community. Gulfport's Arts Center is also a creative hub, offering weekly pottery classes, writing groups, and more. In addition to its yearly Gecko Fest, Gulfport hosts an annual Pink Flamingo Home Tour, inviting visitors to tour some of the unique and historic homes in the area. The city also partners with the Pinellas County Humane Society each year to host a community-wide pet rescue day, a block party with vendors, pet trainings, adoption opportunities, a pet supplies drive, and more. 

Now that you know you need to spend a night or two here, check out Peninsula Bed and Cocktails, Gulfport's vibrant spin on the classic bed-and-breakfast. With rooms themed after classic cocktails like the Espresso Martini Suite and a lobby bar serving Old Florida charm and modern mixology along with afternoon live music, this boutique is an underrated gem and a must-stay when in Gulfport. Rooms start at $161/night during the week, ranging upwards of $630/night during weekends and high season. The Sea Breeze Manor Inn is another small hotel in Gulfport, with rooms themed around islands in the Caribbean, like Jamaica and Barbados. Rooms start around $189/night and can range to about $300/night.