Looking for a fun, quirky town to get away to in Western Florida? Try the coastal town of Gulfport, just south of St. Petersburg. Walk up the historic main street peppered with charming buildings including a quaint hotel, unique shops, art galleries and restaurants.
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Just one hour from my home in Lakewood Ranch, I thought it would be fun for my out of town friends and I to have a girls weekend in Gulfport that claims to be “proudly weird”. The weather in April is exceptionally pleasant and the proximity to beaches and waterways for boating makes it ideal location for a fun time.
The charm of Gulfport is being able to stay in town. We found a nice Airbnb, but the Peninsula bed and cocktails hotel on the main strip in town looks inviting and seems affordable as well.


Gulfport is still rebuilding some areas from last year’s double whammy of hurricanes: Milton and Helene. The waterfront area and piers are fenced off as repairs are still incomplete. As we walked west along the shoreline, the beach was filled with people doing yoga on the sand and children playing at the nearby park.
Our weekend included a third Saturday so enjoyed the Gulfport Night Market. Formerly known as Art Walk and IndieFaire, it takes places twice a month. The night market offers an evening marketplace experience with plenty of live music, local artists and small business vendors to engage the community and visitors as they stroll along the main street.
We enjoyed our Italian inspired dinner at Pia’s Trattoria and I would highly recommend this restaurant. The service was great, the food amazing and the atmosphere felt like you were in another country – Italy? We may have eaten here more than one time.



Just a quick drive from our Airbnb are the beautiful beaches of Pass A Grille. We found free parking for 3 hours on 8th street. With temperatures in the 80s, we spent some time on the beach and in the water, then went to the Hurricane Seafood Restaurant for lunch. The Grouper sandwiches were delicious!

On Sunday, I reserved a pontoon boat with Mad Beach Boat Rentals. They had been located on the waterfront in Gulfport, but got destroyed in the hurricanes. We new waterfront location in St. Pete gave us easy access to the bay area and a few islands.
My brother-in-law who is familiar with boating the coastal waters of Florida assumed the role of boat captain and we had a great afternoon. We followed the channel over to a few islands near Johns Pass. The sunshine and glistening turquoise waters welcomed our smiles as we spotted dolphins swim past our boat. We anchored off the sandbar with a few other boaters and enjoyed watching the dogs enjoy splashing and swimming.




We even wore mini Easter bonnets on our caps for our Easter Sunday cruise
After some time in the water we pulled the boat up to Sea Dog Brewing Co. for a tasty lunch with our crew. Nothing like getting out on the water to lift the soul.
Our final day we visited the beautiful Sunken Gardens in St. Pete. In keeping with the “old Florida” idea, this historic attraction has been around for 100 years. Originally a marshy sink hole where wild hogs roamed, it now boasts tropical palms, orchids, flamingos, parrot shows, and waterfalls. After a walk through the gardens, we found a spot for lunch on Central Avenue in St. Pete before a final goodbye at the airport.
Until our next Florida adventure…




















