Gulfport, FL: Things to Do and Vacation Guide
If you’re heading to Gulfport, Florida for your next getaway, consider yourself fortunate. This charming coastal city has a treasure trove of activities waiting to be discovered. Whether you’re traveling with family or seeking a quick weekend escape, I’ve got the inside scoop on the best things to do in Gulfport, FL. From free attractions to must-try eateries, this comprehensive guide covers it all. You’ll also find valuable insights on where to stay and what to know before your trip.
Don’t rely on generic travel guides or online reviews – as a local, I’ve got firsthand knowledge of the city’s hidden gems and will share my expert tips with you. So, without further ado, let’s dive into the best things to do in Gulfport, Florida.
What is Gulfport, FL Like?
Gulfport, Florida is often misunderstood as a sleepy town, but in reality, it’s an eclectic blend of retiree-friendly charm and artsy flair. While it may not be bustling with energy 24/7, the city has a unique knack for hosting free live music events almost every night of the week, which always seems to draw out the town’s inner party animal.
As someone in my 30s who’s had the pleasure of experiencing Gulfport firsthand, I can confidently say that it’s a hidden gem that effortlessly strikes a balance between its quiet, laid-back atmosphere and vibrant cultural scene.
21 Best Things to Do in Gulfport, FL with the Family (or Your Mom!)
While many tasks on this list can be completed within a half hour, what sets Gulfport apart is its proximity to the vibrant downtown area of St. Petersburg. This charming coastal city may be small, but its compact size belies its ease of exploration and accessibility to surrounding amenities. With a mere 15-minute drive, you can arrive in the heart of St. Pete, making it an ideal base for those seeking to experience the best of both worlds.
Check Out the Gulfport Market on Tuesdays
Every week, Gulfport’s Beach Blvd. transforms into a vibrant marketplace on Tuesdays. From 9 am to 2 pm, locals and visitors alike can enjoy the sights, sounds, and smells of the bustling market. What’s more, this event is a year-round affair, taking place every Tuesday, no matter the season.
Eat at O’Maddy’s and Enjoy the View
There’s something about dining at O’Maddy’s that makes me covet the idea of making Gulfport, FL my home. The restaurant’s prime location offers stunning views of the water and pier, making it a perfect spot to relax and take in the scenery. For me, the real highlight is their Halie’s Blackened Salmon Salad – a culinary masterpiece that never fails to impress.
Enjoy a Book on a Bench
Imagine sinking into a serene setting where tranquility meets breathtaking views. That’s exactly what you’ll find in Gulfport, Florida – picturesque swinging benches that will transport you to a state of calmness as you gaze out at the stunning waters.
Shop on Beach Blvd.
Nestled along the Gulf Coast, the charming city of Gulfport, Florida, boasts a delightful stretch of quaint boutiques and specialty shops that are sure to capture your attention. This compact collection of approximately 5-7 stores offers a refreshing respite from the hustle and bustle of daily life, allowing you to indulge in some guilt-free retail therapy without feeling overwhelmed.
Drive to Clam Bayou Nature Park and Play Disk Golf
Imagine embarking on a unique outdoor adventure with your family, one that’s both fun and free! If you haven’t already, consider exploring the Clam Bayou Nature Park, which boasts its own disk golf course. This activity is perfect for families to enjoy together, and the best part? It won’t cost you a thing! Just remember to bring your own disks, and if you’re new to the game, I recommend picking some up on Amazon.
Keep in mind that the park’s map isn’t exactly user-friendly, so don’t stress too much about getting started or finding your way around.
Take a $10 Dance Lesson at the Casino
The Gulfport Casino offers a variety of dance lessons throughout the week, catering to different tastes and styles. Whether you’re interested in the energetic swing dance, the passionate flamenco, or the fun-filled line dancing, there’s something for everyone. With such a wide range of options, it’s easy to find a night that suits your schedule.
For instance, taking advantage of the swing dance lessons on Wednesdays could be the perfect precursor to hitting the dance floor at Blue Parrot on Mondays.
Go Swing Dancing at The Blue Parrot on Mondays
In Gulfport, FL, Mondays are an ideal night to indulge in a fun-filled evening at home with friends and family by playing board games or cards. Alternatively, you can venture out and experience the vibrant nightlife at The Blue Parrot, located just 12 minutes away from St. Pete Beach. On Monday nights, this popular spot transforms into a lively dance floor, featuring a live band that gets everyone swinging their hips to the beat!
Walk Around the Neighborhoods
Gulfport, Florida’s compact size and pedestrian-friendly atmosphere make it a joy to explore on foot. As you stroll through the charming neighborhoods, you’ll be struck by the vibrant hues and quaint character of many homes. The subtle juxtaposition of slightly weathered facades only adds to their allure.
One delightful game is to try to estimate the original purchase price of these Gulfport abodes, then compare it to their current estimated value. A fascinating exercise!
For instance, some homes that were valued at $50,000 in 2015 have since skyrocketed in value, with estimates now exceeding $750,000.
Take the Kids to the Playground
In Gulfport, Florida, parents can rest assured that their little ones are well taken care of at the kid-friendly playground situated adjacent to the Gulfport Recreation Center. One of its greatest advantages is the fact that it’s usually not crowded, providing a unique opportunity for children to explore and play freely without the usual commotion.
Enjoy the Christmas Lights (in December)
When planning a visit to Gulfport, Florida in December, be sure to stop by the iconic residence located at 2829 57th Street South. This stunning property is transformed into a winter wonderland with an incredible display of Christmas lights that will leave you in awe.
Watch the Sunset
As the day comes to a close, the sky in Gulfport, Florida transforms into a breathtaking canvas. The vibrant hues of orange, pink, and purple paint the horizon, creating a picturesque scene that’s sure to leave you mesmerized. Imagine sipping on a glass of fine wine, feeling the gentle ocean breeze against your skin, as the sunset unfolds its splendor before your eyes.
Find Your Next Husband
With a dash of humor, but also a hint of sincerity, I have to admit that my experience in Gulfport, FL’s vibrant 55+ retirement community, Town Shores of Gulfport, left me with a lasting impression. Comprising no fewer than 18 buildings, this sprawling complex is home to hundreds of residents from various walks of life. During my stroll around the premises, I couldn’t help but notice an unusually high concentration of single men in their 50s and 60s.
What’s more, Gulfport itself boasts a sizeable gay and lesbian community, which adds an extra layer of diversity to the local landscape – and I must say, many of these older gentlemen are still quite fit!
Take a Morning Stroll Along Shore Blvd.
Start your day off right with a serene morning stroll along Shore Blvd., where the tranquility of the surroundings will leave you feeling invigorated. Take in the breathtaking views as you meander through the streets, gradually making your way towards the picturesque Pier. The approximate 6-block journey provides ample opportunity to clear your mind and set intentions for the day ahead.
Get the Beach to Yourself
While some Florida beaches like Clearwater Beach and St. Pete Beach are bustling with activity, Gulfport’s shoreline stands out as a serene oasis. While the water may not be suitable for swimming, it presents an ideal setting for families to create sandcastles or for individuals to relax and indulge in a favorite book. The tranquil atmosphere makes it an attractive spot for kids to frolic and play, while adults can unwind and soak up the sun.
Sit at a Bar and Have a Beer
Gulfport, Florida, may not be the first destination that comes to mind when thinking about vibrant nightlife, but it has its own unique charm. The city’s laid-back atmosphere is perfectly captured at its friendly bars, which offer stunning views of the surrounding area. One such spot is Caddy’s, located on the second floor of the building. Not only do they serve a great selection of drinks, but they’re also a popular spot to catch a Sunday football game with friends.
Play Pickleball at the JW Cate Rec Center
Looking for a fun way to spend your morning? Grab your paddle and pickleball gear and head to the JW Cate Recreation Center, where you’re likely to find a game in progress on weekday mornings. If you time it right, you can join in on the action on Thursday or Friday at 8:30 am when the courts are typically busiest.
Go Thrift Store Shopping
When it comes to thrift shopping in the Gulfport area, there are several options within a 10-15 minute drive. Among them are St. Vincent’s Thrift Shop, Sunshine Thrift Store, and Out of the Closet, which stands out as my top recommendation. Not only is Out of the Closet just a seven-minute drive from Gulfport, but it also offers complimentary HIV testing.
What’s more, all proceeds from the store support local HIV prevention and treatment services, making your shopping experience not only budget-friendly but also socially responsible.
Go Dancing at Night
Almost every weeknight, Gulfport comes alive with the sounds of live music – a treat that’s hard to resist. For those seeking an evening of entertainment, there are plenty of options to choose from. Three local favorites include The Tiki Bar and Grill, Neptune Grill, and The North End Tap House. The latter being my personal favorite, tucked away behind Stella’s.
If you want to get a feel for the vibe at The Tiki Bar and Grill, be sure to check out their live music performance on this YouTube video.
Have Coffee at GulfPerk Coffee Bar
In the charming coastal town of Gulfport, Florida, there’s no shortage of great places to start your day with a cup of joe – even if there isn’t a Starbucks location nearby. One local favorite is the cozy and inviting GulfPerk Coffee Bar, where residents and visitors alike gather in the morning for a caffeine boost. It’s become a beloved gathering spot for the community, and its charm is all part of what makes this coffee shop so special.
Give Kava a Try
If you’re new to the world of kava, there’s no better place to start than at a local kava shop. I haven’t had the chance to try it myself yet, but if you’re interested in experiencing its potential anxiety-reducing and relaxing effects, consider visiting Low Tide Kava Bar as a great starting point.
Have Brunch at Stella’s
When visiting Gulfport, FL, a must-do activity is undoubtedly a visit to Stella’s for brunch. I was introduced to this culinary gem while staying with a friend in St. Pete, who swore that Stella’s serves the best brunch in both cities. The Nola Omelette, Bana Nut Bread French Toast, and creative bloody marys are just a few of the mouth-watering options that will leave you craving more. Trust me when I say that you won’t be disappointed by this top-notch dining experience.
Where to Stay in Gulfport, Florida
Gulfport, Florida doesn’t have any large hotel chains to offer. Instead, travelers can opt for unique and cozy bed-and-breakfast options or vacation rentals. One notable B&B is The Sea Breeze Manor Inn, which offers a warm and welcoming atmosphere.
However, my personal experience with Gulfport has been more focused on vacation rentals. On my most recent trip to the area, I stayed at Jason’s Wine Cellar, a VRBO property that exceeded my expectations.
This charming rental features an enclosed backyard, an open-air game room, two beds, one bathroom, and a well-equipped kitchen and dining area. What made this place truly special was its dog-friendly policy, which allowed me to bring along my furry companion.
If you’re interested in booking Jason’s Wine Cellar, you can find more information on their VRBO listing.
Additionally, Gulfport has a range of Airbnb options available for those who prefer the convenience and flexibility that comes with renting a home.
What to Wear in Gulfport, FL
Gulfport, Florida, embodies a carefree vibe. Leave your formal attire behind – shorts and a t-shirt, a flowy skirt with a casual top, or even loungewear (though you might want to reconsider that last one) are all fair game. The town’s laid-back atmosphere is deeply rooted in its demographics; the majority of residents are over 50 and have earned their right to relax after a lifetime of hard work. Gulfport is a haven for those seeking to unwind, drop formalities, and simply be themselves.
What to Wear in Gulfport, FL in Spring, Summer, and Fall
When visiting Gulfport during the warmer months of spring, summer, or fall, you can expect temperatures to soar. To ensure your comfort, be sure to pack lightweight essentials such as flip-flops, shorts, tank tops, and a sturdy sun hat with a wide brim to shield yourself from the sun’s intense rays.
What to Wear in Gulfport, FL in the Winter (November, December, January, February)
When planning a trip to Gulfport, Florida in the winter, it’s essential to consider the varying temperatures throughout the day. While daytime temperatures are often warm, the nights can still dip down, making layering a crucial part of your packing strategy.
For a comfortable and practical wardrobe, consider bringing shorts and lightweight tops for sunny days, as well as sneakers, pants, a sweatshirt, and a light jacket to accommodate cooler mornings, evenings, and any unexpected temperature drops.
Things to Know Before You Go to Gulfport, FL
For those who have yet to visit Gulfport, Florida, there are a few essential details to keep in mind. First and foremost, this charming coastal city boasts a unique blend of small-town charm and big-city amenities.
It’s not fancy.
Gulfport, Florida embodies a laid-back atmosphere, where residents and visitors alike can shed their pretenses and simply be themselves. There’s no pressure to present a polished image or worry about making a good impression – just relax and enjoy the easy-going vibe.
Gulfport gets going after 10 am.
No Starbucks and no grocery store.
Gulfport, Florida, may not boast the familiar sights of major chains like Starbucks or traditional grocery stores, but it does offer unique alternatives that are just as appealing. For instance, you can still get your coffee fix at Gulfperk Coffee Bar, where a warm and welcoming atmosphere awaits. Additionally, residents and visitors alike can find fresh produce, meats, and other essentials at the charming Neighborhood Fresh Market.
The main street is Beach Blvd.
Located in the heart of Gulfport, Florida, a single prominent thoroughfare dominates the city’s landscape – Beach Boulevard. Stretching merely four blocks from Siri’s Gourmet Burgers & Pizzas to the iconic Gulfport Casino Ballroom, this compact yet vibrant street serves as the epicenter of local activity and commerce.
It gets HOT in the summer.
When it comes to exploring Gulfport, Florida during the summer months, one thing is certain – the scorching sun can be unforgiving. With minimal natural shading, it’s crucial to prioritize your comfort level by packing essential items like a hat to protect your face and neck from those harsh UV rays.
Mostly people over 50.
What struck me during my week-long stay in Gulfport, Florida, was the stark demographic reality. The city’s population appears to be predominantly composed of individuals aged 50 and above. In fact, it wasn’t until the end of my visit that I caught a glimpse of a few people under the age of 45, with children being an extremely rare sighting – I didn’t see a single kid during my entire time there.
Lesbian and gay friendly.
Gulfport boasts a welcoming atmosphere for members of the LGBTQ+ community, with an openly visible presence of lesbian couples enjoying meals at local eateries and older gay gentlemen strolling through the city. The town’s relaxed vibe fosters an environment where individuals can be themselves without fear of judgment or discrimination.
Lots of parking.
One of the most appealing aspects of visiting Gulfport, Florida, is the abundance of parking options available, which includes beach parking spots. What’s even more enticing is that all of these parking facilities are completely free to use, making it an ideal destination for those who value convenience and affordability.
Not touristy.
While Gulfport, Florida may not be a bustling tourist hub, its laid-back atmosphere is precisely what draws many visitors to this coastal city. With a lack of flashy attractions and a focus on simple pleasures, Gulfport offers the perfect setting for those seeking relaxation and rejuvenation.
Only 15 minutes from St. Pete.
Tucked away in Gulfport, Florida, lies a charming treasure waiting to be discovered. What’s more, this coastal city boasts an impressive proximity to the vibrant downtown area of St. Petersburg, with the drive taking only 12 minutes – a fact I’ve personally verified for your convenience.
Quiet on Mondays
While weekdays can be surprisingly peaceful in Gulfport, Florida, one day stands out as particularly tranquil: Monday. With the hustle and bustle of weekend activities behind us, Mondays often feel like a breath of fresh air in this coastal city. Consider dedicating your Monday evening to quality time with loved ones – whether that’s a family game night, an evening of card games or simply some well-deserved relaxation.
Summary – Things to Do in Gulfport, FL
Gulfport is an unexpected gem just 15 minutes west of St. Pete, Florida, boasting a unique blend of laid-back charm and artistic flair. The town’s essence lies in its cultural attractions, which are best experienced by strolling along Broadway Street to discover eclectic shops, and then meandering along Beach Drive to uncover local bars and restaurants.
As the sun sets, head to the casino for a dance lesson or simply enjoy the lively atmosphere of one of Gulfport’s many small bars, where live music fills the air. What sets Gulfport apart from its more fast-paced counterparts in Tampa and St. Pete is its unwavering commitment to relaxation – perfect for sipping sunrise cocktails, watching the sunset over a glass of wine, or simply dancing the night away with the locals.
Regardless of age, you’ll find Gulfport an ideal destination, catering to families with kids and offering a safe and welcoming environment. If you have any questions about Gulfport, feel free to leave a comment below, and I’ll be more than happy to address them. Trust me – you won’t be disappointed!
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