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Small, quirky and fun, Gulfport is a hidden gem in Pinellas County. Gulfport is the perfect, quaint, spot for your next day trip with someone special. Explore nature preserves, hit the beach, enjoy some live music, grab a cocktail and dine at some of Pinellas County’s most delicious restaurants – all without leaving the tiny town of Gulfport.

Updated July 2023, by Zoë Joiner


Planning Your Day In Gulfport, Florida


Where To Eat in Gulfport

  • Stella’s
  • Caddy’s Gulfport
  • Pia’s Trattoria
  • The North End Taphouse
  • The Wine House

There are several longtime favorites located in Gulfport, perfect for a date day or night. Stella’s is a great brunch spot located right in the heart of Gulfport. Open 7 am to 2 pm daily, Stella’s serves breakfast, brunch and lunch all day, with a full complement of beer, wine and cocktails. Enjoy their great outdoor seating with a bloody Mary in hand.

Head a little closer to the beach to Caddy’s Gulfport for lunch. Caddy’s has a great location with a rooftop offering panoramic views of the bay. This is the place to go for fresh seafood and tropical drinks. 

Pia's Trattoria patio Gulfport, FL
Image credit: Pia’s Trattoria | Photo by Bear Karry Productions


For the ultimate romantic night out, Pia’s Trattoria is a must-visit. Pia’s Italian meals are fresh, organic, and made to order. They offer standard Italian dishes such as gnocchi and lasagna served in an iron skillet, as well as an array of pastas and meat plates including Chicken Parmesan and Veal Marsala.

If you’re trying to keep things casual, stop by The North End Taphouse for locally brewed beers and seltzers and a deli-style menu of snacks, sandwiches and hot dogs. North End has ample outdoor seating and a chill neighborhood vibe, with seemingly omnipresent live music. It is the perfect vibe for a relaxed visit to Gulfport, Florida, but Note: they are closed on Sundays during the summer.

In the mood for some delicious BBQ? Enjoy it with a glass of wine at The Wine House on Beach Blvd., right in the heart of the historic waterfront district. Go for a funky and chilled-out happy hour (weekdays until 5:30pm) for $6 wines, build your own charcuterie boards or pig out on tender house-smoked brisket. They even offer yoga on Thursdays if you’re feeling motivated.


What To Do In Gulfport 

  • The Village Courtyard on Beach Boulevard
  • Gulfport Tuesday Fresh Market
  • Gulfport Casino (for events and dance lessons)
  • Clam Bayou Nature Preserve

Many of Gulfport’s restaurants and bars are located in The Village Courtyard on Beach Boulevard. It’s a great area to stroll the shops and grab a drink or bite to eat. In addition to the restaurants and bars, you’ll find a nail salon to grab a pre-beach pedicure, a gourmet market, and a bandstand that hosts live music, trivia or entertainment every night of the week. Note, The Village Courtyard is closed on Sundays.

If you find yourself in Gulfport on a Tuesday, you’re in for a treat. The weekly Gulfport Tuesday Fresh Market is one of the longest running farmer’s markets in the county and is open 9 am to 2ish every Tuesday, year-round, 

Photo Credit: St. Petersburg Parks & Recreation


Down by the beach is the Gulfport Casino – but not the kind of casino you’re thinking of. Nearly 100 years old, the Gulfport Casino Ballroom is right on the beach and serves as a venue space for rent. It also hosts ballroom dance events and lessons every Sunday, Tuesday and Thursday (and swing dancing on Wednesdays).

Just outside Gulfport is the Clam Bayou Nature Preserve. There are walking trails and boardwalks, and it is a great place to kick off a paddleboarding or kayaking adventure. 


Where to Stay in Gulfport, Florida

Photo Credit: The Peninsula Inn


You won’t find any big-name hotels in Gulfport, but even better, we recommend the historic Peninsula Inn. It’s currently closed for renovations but check back soon to book a freshly-updated stay at this primo location, just steps from restaurants, the Village Courtyard, and the beach. 

The Sea Breeze Manor Inn is another standout B&B with a great location directly across from the beach. Built in 1923, it’s a spacious and charming Tudor-style home with a courtyard and private, beach-front patios available. Enjoy an delicious outdoor breakfast/brunch from its Sea Breeze Cafe right on the patio overlooking Boca Ciega Bay. You can even bring your pup to stay in one of the 2 pet-friendly cottages.

From here you also have quick access to St. Pete Beach, so check out our guide to the St. Pete beach bars if you’d like to make a side trip.


Feature image from Wikimedia commons (with cropping to 800 × 533 px)