Set on the gentle waters of Boca Ciega Bay, the small town of Gulfport delivers a mix of Old Florida charm and bayside leisure. Once a humble fishing village, Gulfport has managed to stay delightfully unpolished even as the larger Tampa Bay metro area expands around it. Take a slow walk along the waterfront pier between Shore Boulevard and Beach Boulevard for sunset views — if you’re lucky, you might catch a glimpse of dolphins cutting through the shallows. From the Municipal Marina, rent a kayak or paddleboard to explore the mangrove-fringed estuary of Clam Bayou Nature Preserve where herons and osprey stir in the salt air.

The Gulfport Beach Park draws a mellow crowd to its calm shores and is still just steps from art galleries, museums, and restaurants. The compact town layout means you can park once and spend the day exploring on foot. Getting to Gulfport is easy, with Tampa International Airport (TPA) and St. Petersburg-Clearwater International (PIE) both within a 30-minute drive. Once you arrive, the pace slows to match the tide. To extend your visit in the area, consider continuing on to Safety Harbor, known as the “Jewel of Tampa Bay.”

If Gulfport has a pulse, it beats strongest along Beach Boulevard, where galleries, vintage shops, and sidewalk cafés radiate local color. The town’s long-standing embrace of the offbeat has made it a haven for artists, writers, and makers who prefer brushstrokes over big-box stores. On the first Friday and third Saturday of every month, the Art Walk transforms the streets into an open-air gallery. Musicians play, artists paint live in The Village Courtyard, and the scent of fresh seafood drifts from waterfront restaurants. Between events, galleries showcase everything from blown glass and hand-stitched textiles to vivid paintings of Gulfport’s own oak-lined streets.

For overnight stays, opt for character over corporate. The Peninsula Inn & Spa, housed in a lovingly restored 1905 building, anchors the town’s lodging scene. You’ll also find cozy cottages and boutique inns that mirror Gulfport’s creative, walkable spirit. Dining is as eclectic as the décor. Expect Venezuelan comfort food, dockside seafood, and small wine bars tucked beneath the oaks. The vibe is unhurried and communal. This is a town for browsing, chatting, and lingering over a second cup of coffee. If you’re looking for more artsy Florida communities to explore, check out mural-filled DeLand, known as the “Athens of Florida.”

Long before it became a bohemian hideaway, Gulfport began as Barnett’s Bluff, settled in 1868 by James and Rebecca Barnett. Over time it cycled through a few identities — Disston City, Bonifacio, Veteran City — before officially becoming Gulfport in 1910. Its enduring symbol, the Gulfport Casino, has been the town’s social anchor for more than a century. The current 1930s-era building, listed on the National Register of Historic Places, still hosts dances and community events overlooking the bay.

That independent streak still defines the town. Gulfport’s dining scene skips national chains in favor of small, personality-driven spots. The Pink Winehouse, known for its wines, barbeque, and chill vibes, is a local favorite. Most guesthouses and short-term rentals sit within walking distance of shops, the marina, and the bayfront park, making it easy to experience the town without a car.

Parking is free and plentiful, and the Gulfport Historical Society offers walking tours that uncover the stories behind the cottages, piers, and historic homes. Together, they reveal a town that’s grown with grace: colorful, creative, and confident in its quirks. If you have time during your trip to Gulfport, make the journey to some of these other spectacular beaches around Tampa Bay.