Last Updated on December 14, 2023 by Marybeth
Or it’s highly likely you’ll decide to just stay put in vibrant, historic Gulfport.
There IS so much excitement going on in downtown St. Petersburg – most notably new restaurant openings. Read a comprehensive list of them at Creative Loafing. And the rebuilt, famous St. Pete Pier. Not to mention the gorgeous St. Petersburg waterfront. You’re going to want to visit. Off and on while you stay in downtown historic Gulfport. In between some beach days at St. Pete Beach.
Gulfport is the perfect location to do both. In under 15 minutes you can be walking out on the St. Pete Pier, or if you turn in the opposite direction the beach is less than 5 miles away from Gulfport. This colorful little town is a complete destination in itself, and you never have to worry about parking, or crowds.
Stroll the shady Main Street Arts District, with its shops, restaurants and galleries a block away from – and some overlooking – the water. Gulfport has its own beach! Bring your travel partner and bat a volleyball around on the courts, or just put your feet in the sand and take in that view. Beach yoga and drum circles happen here.
Spend the day exploring colorful Gulfport and you may never want to leave. In fact we barely did!
You will have no parking problems in Gulfport. Precious remained parked in the driveway of our bungalow for most of our visit as Gulfport is one of those walkable towns with everything you need within an easy distance. If you’re visiting for the day there is plenty of free parking around town and at the waterfront Gulf Beach Park.
THE BEACH
5500-5800 Shore Blvd. South
This 6.8 acre beach overlooking Boca Ciega Bay may not have surf-able waves but total relaxation can be the goal for the day. Gaze across the water at the Pinellas Bayway, St. Pete Beach, and you may even see the grand pink Don Cesar Hotel. Walk the trail, meander out onto the Walter and Bert Williams Fishing Pier to cast a line. Listen to music – the Pavilion Music Group performs several times a week.
Rent a boat from Fun Unlimited Sports, charter a boat from Gulfport Yacht Charters.
Gulf Beach Park also has a fenced playground and restrooms.
THE BAR
Ohhh, bars. One of our favorite spots to while away a late afternoon post-beach, listening to live music and enjoying the treat of something fried paired with a cocktail.
In Gulfport the choices of outdoor seating to dine and drink are so many, we didn’t choose just one like we often have in the past.
Overlooking the water and the fishing pier, all with outside seating:
O’Maddy’s Bar and Grille. Enjoy the view, live music, and their giant menu including Beef on Weck (I had to look it up, it’s a kind of bun popular in Buffalo NY or possibly Germany… doesn’t matter where, it’s delicious); Jamal’s Hangover; Big Mom’s Lobster Mac & Cheese. In other words, something for everyone.
Also along the waterfront are Neptune Grilland The Tiki Bar & Grill.
Along Gulfport’s main street, Beach Boulevard:
Siri’s Gourmet Burgers & Pizza
THE BUNGALOW
We had the happy opportunity to stay in this fully renovated, amazing 1927 Craftsman Bungalow as the “quality control team” to make sure the place was renter-ready (as it was the owner’s first time preparing a vacation rental.) At the time of publication this Art District Bungalow is available from May or June through November 2021. As these dates are subject to change, contact Bryan at Gulfport Art District.
For a short term stay we recommend this Gulfport Beach Studio, an artistic spot perfect for two people.
This Gulfport Beach Studio has a queen bed, newly renovated bathroom, kitchenette, shady private backyard, just steps to the beach and Beach Blvd., with a rate of approximately $100/night. Enter your dates on their AirBnB site for exact pricing. This studio was recently designated one of the Top 10 AirBnbs in Florida by Timeout Magazine!
If your group is larger the next door cottage is for rent as well, a 2/2 accommodating 4 people. The owners of both are SuperHosts!
Another option is The Historic Peninsula Inn, which offers luxurious rooms and suites and has an interesting history – a fishing lodge turned boutique inn! You would never guess its humble beginnings to see it now, with the original small rooms (just a place to sleep in between fishing) opened up joining multiple spaces to create cozy guest rooms with luxe bedding and many amenities including complimentary breakfast. Some rooms are pet-friendly!
And I can’t leave yet without showing you some enchanting shops, the casino, and creative bungalows around town…. because, well, bungalows. It is our last name, after all….
Have you visited Gulfport, Florida? If so, did you settle in for the duration or venture out and explore? Let us know in the comments!
Gulfport is on Florida’s west coast, 22 miles south of Clearwater Beach and 25 miles southeast of Tampa.
4 Comments
Scott sharlow
When you mention Salty’s sandwhich shop in Gulfport you are showing a photo of O’Maddys Bar and Grill which is the corner place right next to Salty’s.
Marybeth
Hi Scott, yes, I guess I need to go back and clear up the description etc. on that photo; I thought I noted that it was O’Maddy’s as well. I didn’t get a pic of Salty’s Sandwich Shop but wanted to reference it since Salty’s the bar doesn’t serve food. Thank you!
Ann jochems
I relocated to Gulfport from Long Island when I retired in 2017. It is one of my better decisions. It is truly a gem. There is much to do and see and it is my retirement paradise!
Marybeth
Thanks Ann, I have heard so many wonderful experiences like yours! Gem is certainly a perfect description. As I was walking around taking photos one early morning I met a man who had just moved there and (while keeping our distance, socially!) we spoke about the town. He was so thrilled to be there and I could hear it in his voice. Yay for your retirement paradise!