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.
Planning Your Day In Gulfport, Florida
Where To Eat in Gulfport
- Caddy’s Gulfport
- Pia’s Trattoria
- The North End Taphouse
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.
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.
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 is often hosting live music and entertainment.
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,
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 is right on the beach and serves as a venue space for rent and is home to dance events and lessons. 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
You won’t find any big-name hotels in Gulfport, but even better, we recommend the historic Peninsula Inn. Steps from restaurants and the Art Village Courtyard, and just a couple blocks from the beach and Casino, The Peninsula Inn has the perfect location for your weekend in Gulfport, Florida. 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.
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