The Best Place to Stay While Exploring Downtown St. Petersburg and St. Pete Beach: Historic Gulfport

Last Updated on May 16, 2024 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. Creative Loafing is a great place to find out about what’s new in the area. And the rebuilt, famous St. Pete Pier with its events, restaurants, Marketplace vendors, and multiple awards has added new dynamism. 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

Gulf Beach Park

Volleyball courts with the Gulfport Casino in the background

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.

You may have the beach to yourself!

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.

O'Maddy's Bar and Grill and Salty's Gulfport both overlooking the water in Gulfport Florida
O’Maddy’s Bar and Grille, on the right

The Tiki Bar and Grill in Gulfport Florida
The Tiki Bar & Grill

Also along the waterfront are Neptune Grill and The Tiki Bar & Grill.

Along Gulfport’s main street, Beach Boulevard:

Pia's Trattoria in Gulfport Florida
Pia’s Trattoria

Pia’s Trattoria

Gulfport Brewery and Eatery
Gulfport Brewery and Eatery (now painted a fun turquoise! Need to go back and update our photo!)

Gulfport Brewery and Eatery

Golden Dinosaurs restaurant in Gulfport Florida
Golden Dinosaurs

Golden Dinosaurs

Stella's in Gulfport for breakfast brunch and lunch all day
Stella’s, for breakfast, brunch, and lunch all day

Stella’s

The North End Tap House

Siri's Gourmet Burger and Pizza Gulfport Florida
Siri’s Gourmet Burgers and Pizza

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.)

Art District Craftsman Bungalow kitchen in Gulfport Florida
There are many stunning professional photos at Gulfport Art District but I had to show you the gorgeous kitchen where they kept the original ceiling!

For a short term stay we recommend this Gulfport Beach Studio, an artistic spot perfect for two people.

Gulfport Beach Studio Airbnb front view
Photo courtesy of Gulfport Beach Studio
Gulfport Beach Studio AirBnB perfect for 2 people
Photo courtesy of Gulfport Beach Studio

This Gulfport Beach Studio has a queen bed, newly renovated bathroom, kitchenette, shady private backyard, just steps to the beach and Beach Blvd. Enter your dates on their AirBnB site for exact pricing. This studio has been 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 Peninsula Bed & Cocktails, 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. You can choose your room based on the essence and ambiance of your favorite cocktail!

The Historic Peninsula Inn in Gulfport Florida
The Peninsula Bed & Cocktails

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….

Bo Tiki Boutique Gulfport Florida
Bo Tiki Boutique
Shops around town in Gulfport Florida

The Gulfport Casino
The Gulfport Casino, a historic landmark and one of the few of its kind still operating – not as a casino, but an events space.
Cute two story pink house in Gulfport Florida

Turquoise bungalows with yellow and coral trim in Gulfport Florida

A tiny turquoise fixer-upper in Gulfport Florida
So cute and intriguing!

Reef Dogs Gifts and Grooming

Purple cottage with a red picket fence Gulfport Florida

White bungalow with green trim under huge shade trees Gulfport Florida

Turquoise cottage with white picket fence Gulfport Florida

Have you visited Gulfport, Florida? If so, did you settle in for the duration or venture out and explore?

Gulfport is on Florida’s west coast, 22 miles south of Clearwater Beach and 25 miles southeast of Tampa.

A graphic titled The Best Place to Stay While Visiting Downtown St. Petersburg and St. Pete Beach: Gulfport, along with a photo, for adding to a Pinterest board

4 Comments

  1. 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.

    1. 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!

  2. 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!

    1. 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!

Leave a Reply

Your email address will not be published. Required fields are marked *

Social media & sharing icons powered by UltimatelySocial