Under ten miles from St Pete is the charming waterfront town of Gulfport, Florida. Gulfport is a waterfront town often referred to as the Gateway to the Gulf. It’s a hippie town with a fitting, unofficial slogan “Keep Gulfport Weird.” You’ll find a lot of artists and other creatives in this colorful town. Even the cottages are colorful, many are original and no two are quite the same.
Things to do in Gulfport, Florida
Best Places to Shop in Gulfport, Florida
I love wandering the streets of Gulfport and stopping into all of the small shops. The shops here have a small town feel with each of them selling unique items. Some of my favorite shops are Paw Paw’s, which has a little bit of everything for dogs and cats. Sometimes, you’ll even run into their dog employee. Beach Bazaar has a little bit of everything; clothes, artwork, antiques, home decor, souvenirs, and more. But most unique (at least, in my opinion) is that this is also a post office. There are also several boutiques.
Gulfport Casino
The Gulfport Casino is not an actual casino. It got its name because casino refers to “a public room or building used for social meetings, dancing, or gaming” and that’s exactly what this used to be. The Gulfport Casino is a historic site that was built in 1906. It has been used as a station and ticket office, post office, and concession stand. The building was remodeled in the 1930’s. Currently, the casino can be rented out and there are many dance events held at the casino.
Events in Gulfport, Florida
One of the things I love about Gulfport is how community-oriented it is. People who live here take pride in their community and people who visit love visiting. There are several community events throughout the year which are loved by both locals and visitors alike.
Gulfport Fresh Market
Every Tuesday, you’ll find the Gulfport Fresh Market. Most markets in the area shut down during the summer months because the weather can be sweltering, but the Gulfport market stays open year round. You’ll find a variety of food, handmade products, and even local authors. There are also artists and crafters as well as live music.
Geckofest
Gulfport celebrates the end of summer with a celebration called Geckofest. There is live music, art and craft vendors, children activities, food, street performers, and more. There is also a costume contest, parade, bar crawl, and a street dance. The event is family friendly and there is no admission charge.
First Friday Art Walk
On the first Friday of each month, Gulfport has an art walk from 5pm to 9 pm. The streets will close for artists, musicians, and more, to fill them with their talent and items for sale.
Best Restaurants in Gulfport, Florida
For such a small town, there is no shortage of restaurants.
Gulfperk is where I start almost every trip to Gulfport. Gulfperk Coffee Bar is one of my all time favorite places to get coffee. They always have a good featured flavor and everyone who works there is really nice. Usually we take the coffees to go, but sometimes I’ll meet a friend there for coffee and we’ll hang out outside while we chat and enjoy – Gulfperk has a really nice indoor and outdoor area.
Pop Goes the Waffle serves a variety of unique waffles and donuts. Some of their flavors include maple bacon and fruity pebbles. They originally got their start as a food truck and have since expanded to this storefront in Gulfport. If you are planning a trip, keep in mind that Pop Goes the Waffle is only open on Saturdays and Sundays at this time.
Pia’s Trattoria is Italian food. The outdoor seating and atmosphere is amazing, it will make you feel like you’re actually in Italy. This is a great place for good food and a romantic date.
O’Maddy’s Bar & Grille serves good drinks and bar-type food. They have a great location right across the street from the water. O’Maddy’s always attracts a crowd and is often busy when we visit. Locals and visitors both love this place.
Best Places to Grab a Drink in Gulfport
Gulfport Brewery is always a fun stop. They have a really nice outdoor atmosphere and very friendly staff. Of course, their beer is great too, and they have a good happy hour from 3-6pm Monday through Friday. If you don’t have plans at one of the restaurants I mentioned above, the brewery has great options. They have somehow managed to master craft beer and their menu; they have genuinely good food.
Hurricane Eddie’s is a true beach town type of bar and is a great hangout among locals. They have live music on Fridays and Saturdays and there are plenty of TVs for watching the game. They do not serve food at this location but you can bring food there if you’d like.
Caddy’s is also a restaurant but I prefer to stop in for a drink. They have tropical drinks that will really make you feel like you are on vacation as well as good happy hour deals Monday through Friday from 11-6. Caddy’s has a great location in the heart of Gulfport right across from the water.
Blueberry Patch is a unique venue, which I’ve heard described as a “local hippie gem.” They have open mic nights, live bands, and open jam nights (where participants can bring their own instrument). Their mission is to promote peace, love, creativity, and joy. Their outdoor area is large and filled with unique art. It is bring your own beer (or preferred drink) and you can bring your own food as well. It’s also worth noting that they are only open on the 1st, 7th, 11th, and 22nd of each month.
Where to Stay in Gulfport, Florida
If you’d like to stay in Gulfport longer than a day, there are several accommodations. The Sea Breeze Manor is a bed and breakfast with a good location and views of the bay. It is in a historical building, built in 1923. Currently, the Historic Peninsula Inn is closed for construction but on your visit, it may be worth checking to see if they are back open. The Historic Peninsula Inn is a dog friendly hotel built in 1905. It served as a hospital in WWI and WWII. It is in a great location in the heart of downtown. There is a restaurant on site named after the inn’s ghost but don’t worry, she is friendly.
If you’re planning on visiting Gulfport, I hope this post was helpful to you. There are a lot of things to do in Gulfport, Florida, so you’ll be sure to find something to enjoy. It truly is a gem of a town to visit!
