O'Maddy's in Gulfport Florida

By Published On: October 18th, 2022

O’Maddy’s in Gulfport FL

Published on 10/18/22: Before I discuss one of our favorite spots for casual dining w/ a water view & live music, SWFL says “thank you!” for your support these last 20 days. Yesterday, your supplies once again made a difference. This was Colt’s first visit to the barrier islands where Ian’s eye came ashore. Pine Island resident, Tracy Jo Smith, has been LSP’s eyes on the ground these last two weeks. Yesterday she found us a home to assist w/ cleanup (unlivable at the moment). Seems like a drop in the bucket, as many are essentially starting over, but Tracy says it’s all adding up. Thanks to you, on my @LovingStPete social media “stories” you’ll see that we also had a packed SUV of cleaning/recovery donations for a mobile home park.

O’Maddy’s in Gulfport

Shifting gears to more typical LSP posts: O’Maddy’s in Gulfport! What a great spot! Walking by, it quickly stands out as a friendly neighborhood hang out, however a “foodie” friend steered us to O’Maddy’s long ago for their menu. Actually, so did more than 4,400 Google Reviewers, as this bar & grille carries a solid 4.6/5 average. Even better, it’s been around 30+ years and is owned by Gulfport native Maddy Guenther and her husband Joe!

Boaters Rejoice – Dock across the street!

O’Maddy’s has great atmosphere, food, drinks, plus water views. Boaters can dock across the street by the Gulfport Casino. It’s also kid friendly, providing Colt a nice selection from the kid’s menu. They even have “Colton’s Cheeseburger”!

O’Maddy’s Has Live Music

As you know, our family loves live music. Fortunately, O’Maddy’s checks off this box as well, frequently hosting great musicians! For whatever reason, I get the Sloppy Joe’s (Key West) vibe when visiting. Anyone else? That’s a good thing in my book, at least based on the Sloppy Joe’s I grew up visiting (has been a while for me). Follow their account for specials, for instance $3 House Margarita’s on Mondays. And on Sunday, $3 mimosas and Bloody Mary’s.

When you finish your food and drink, make sure to cross the street for a stroll along the waterfront! And if you have kids, the huge Gulfport playground (covered!) is just a 4-5 minute walk away, essentially on the beach.

Owned by the Guenthers

Per a Patch.com article: “Joe Guenther is the general manager and his wife Maddy is the owner. He explained that many years ago she wanted to open an Irish pub, so she simply put an ‘O’ in front of her name and went into business. That was 1989 and the location had been in her family for years before that. One side of the building was formerly a snack bar and a gas station stood at the corner building.”

O’Maddy’s in Gulfport – Expansion Plans

O’Maddy’s has been in the news recently because the owner, Joe Guenther, has plans for expansion. Per the @gabber newspaper: “The Gulfport Community Redevelopment Agency, which consists of members of the City Council, voted July 7 to approve a conditional use and special permit through a site plan for additional outdoor seating on a proposed second-floor addition to the existing restaurant.[…] The restaurant plans 70 seats for the upstairs area, City Manager Jim O’Reilly said.”

Google Reviews: 4400 with a 4.6 average

Address: 5405 Shore Blvd S, St Pete

Phone: 727-323-8643


Bar Open Daily: 8am – 3am
Kitchen is open Sunday-Thursday: 11am to 9pm and Friday-Saturday: 11am to 10pm

I’m a St Pete and Tampa Realtor, Florida native and know our area well! When you use my LovingStPete Team to buy or sell a property, you’ll receive up to $10K at closing! I started LovingStPete on Facebook and Instagram to help clients and others learn about our area. It’s now followed by over 25K people! If you have any real estate questions, simply contact me. My past includes developing a vacation rental advertising company, which I ran for a decade, and then sold to HomeAway/VRBO.

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Written by : St Petersburg Realtor, Mike Braswell

Mike Braswell is a Tampa Bay Realtor, serving St Petersburg, Clearwater, all nearby beaches and more. Mike started LovingStPete in October of 2020 after a difficult year took its toll on local businesses. After being cooped up for portions of 2020 (lockdown) Mike and his son decided to get out and explore, helping spread the good word about the local area he loves so much. Often even doing gift card giveaways to support local. LovingStPete is now followed by over 48 thousand people on social media! The majority of posts are informative on fun parks, activities, day trips, great restaurants, and in general provide a comprehensive tour of the area!

Soon after receiving his bachelors in Management Information Systems, Mike developed and then operated a vacation rental advertising business for 10+ years as CEO/Owner. The business was eventually acquired by VRBO. Mike has earned the trust of many large clients over the years. Such as NFL, Wynn Resorts, Blue Cross Blue Shield, VISA, Genuine Parts Company (NAPA Auto Parts), AT&T, and other Fortune 500 companies.

When not spending time with his beautiful wife and energetic son, Mike enjoys boating and is also an avid tennis player. An interesting fact about Mike is that he grew up on an avocado farm with over 15 varieties, some of which you can find in our local Publix/Winn Dixie as his dad still farms the same farm at 87 years old!

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