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  • Writer's pictureChelsea Susan Bednar

A Day Trip: Gulf Port

The sun sets across the ocean shore, the light reflecting onto the historic buildings that line the Main Boulevard. A lively spirit fills the air as people peruse the many artisan booths outside the local shops. As a light ocean breeze flows through the streets, couples and families dine at the outdoor tables amidst the warm evening air. This is Gulfport, the creative gem of Pinellas County, Florida.


Treasure Island and St. Petersburg may be the larger attractions in the area, but the eclectic town of Gulf Port is not to be missed! This artistically vibrant neighborhood has been known to foster creativity, celebrating its uniqueness with all who come to experience it. This town of small businesses and creatives has been a pillar for the LGBTQIA community, and continues to celebrate its inclusivity with rainbow murals painted on the sidewalks and pride flags displayed in most storefronts. The downtown area is entirely accessible by walking or biking, highlighting its beautiful ocean views along the way. Stroll along the main boulevard and follow its path to the waterfront, where it opens up to a public park and beach recreation area. Play volleyball, wade in the ocean shore, or dine at one of the many nearby restaurants. Shop small and support a few of the local boutiques that line the historical streets. Gulf Port's community actively supports its makers and likeminded creatives, and welcomes everyone to come be a part of the fun.


In the Morning:


Arrive in the late morning just in time for brunch - you’re on island time now, and the locals love to take it slow. Despite its size with a grand total just under three square miles, Gulf Port is known for having some of the best restaurants in the area. Grab brunch at The Breeze Waterfront Cafe, known for its breakfasts catering to both meat lovers and vegetarians. Sip on a freshly brewed coffee as you overlook the the oceanfront on the patio seating. Alternatively, grab something to go from Gulf Perk Coffee Bar, a local favorite. As the town wakes up, take a stroll along the waterfront on the historic Williams Pier, a hot spot for sunsets and site seeing.


In the Afternoon:


Peruse the colorful storefronts and independent boutiques as you find your way to lunch. Gulf Port is proud to represent small businesses, with no chain stores to be found in the area. There are various day activities to participate in, including a walking tour by the Gulfport Historical Society in the downtown area, the waterfront beach overlooking Boca Ciega Bay, the massive skatepark and volleyball court, and a play area for families with children. Food options are plentiful and all within walking distance, but we recommend grabbing a bite at a local favorite, Golden Dinosaurs: a delight for everyone (especially vegans and vegetarians).


If you happen to be in town on a Tuesday, you’re in luck! The Gulfport Fresh Market is every Tuesday, all year round! Shop organic produce by local farmers, freshly baked breads, cheeses, desserts, and even handmade bath and body products. Seasonal changes affect the hours very slightly, open January-April from 9am-3pm, and May-December 9am-2pm.


Want to spend your afternoon out and about? Take a boat tour from the Municipal Marina or rent a kayak to tour the Clam Bayou Nature Preserve. Have fun and explore, and return for the exciting evening events the town has to offer.



In the Evening:


Plan your day trip around the First Friday Artists Market! The town actively supports local artists and makers at the weekly outdoor market, where small businesses stay open in the evening and artisans set up booths on the sidewalks. Shop everything from paintings, handmade jewelry, food, books, apparel, and other odd trinkets as you stroll the marketplace. This free event is from 5pm-9pm every first - Friday of the month (weather permitting). Parking is also free, so you’ll have more to add to your shopping budget (wink wink).


In the mood for beachside live music? Try Gulfport’s Caddy’s (yes, there is a second location here in addition to Treasure Island)! Toast a friend with a couple brews while overlooking the best panoramic views of the oceanfront while the sun sets. For those in the mood for finer dining, make reservations at Half Shel Oyster House. Get the authentic flavors of the area in a classic ‘Surf & Turf’ dish, while cleansing your pallet with their ‘Pink Pearl Martini’. Craving a taste of Italy? Pia’s Trattoria is the best spot for incredible Italian cuisine, with the venue alone transporting you to the feeling of being in a little villa somewhere off the Amalfi coast. O'Maddy's Bar & Grill features live music every Thursday through Saturday, and hosts Karaoke every Thursday through Sunday!


Gulfport’s PRIDE festival is one not to be missed, with the whole town partying it up in support of the LGBTQ+ community. This annual event is in support of the award-winning LGBTQ Resource Center of the Gulfport Public Library, and benefits go towards the organization.


Exciting events happen year round in the area, with Treasure Island, St. Pete, and Tampa only a short drive away. Whatever it is you come to Gulf Port for, we promise you’re in for a good time.



The Sunset Team



Partying it up in Key West? Visit our sister property Marrero's Guest Mansion with {verdigreen} Hotels.



Stay in touch! Follow us on Instagram and Facebook, and tell us about your stay over at Trip Advisor. Feel the ocean breeze yourself - come visit us at Sunset Inn at Treasure Island, Florida.

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