As the only girl in a family of boys, I’m always hunting for destinations that make all of us happy — especially me! Here’s how we did Madeira Beach. 

By the time February rolls around in Iowa, winter feels endless. The magic of Christmas is gone, it’s been bitterly cold for months, and the warmth of the sun is only a distant memory. It’s brutal. There’s one, and only one, cure for the Iowa February blues: finding somewhere else to go! This year, we chose to go to Madeira Beach, Florida for a few days.

Madeira Beach is a tiny, beachside barrier island community bordered by the Gulf of Mexico to the west and St. Petersburg to the east. With a population of just under 4,000, its economy thrives on tourists eager to soak up the sunshine. While Hurricanes Helene and Milton hit hard in the fall of 2024, leaving boarded-up shops and homes, the community had made significant recovery by the time we visited.

Our VRBO condo was across the street from Madeira Beach, the perfect blend of accessibility and affordability. Easily $100 cheaper per night than the condos directly on the beach, we enjoyed gorgeous ocean views and extra cash in our pockets to spend on shopping and restaurants. Our condo complex also had a pool, which if given the chance, our boys would’ve been happy to stay there the entire trip.

The vibe of Madeira beach was easygoing and unhurried, with both residents and semi-permanent snowbirds welcoming and friendly at every turn. We were ahead of the spring break crowds and enjoyed being able to browse quiet shops and stroll uncrowded beaches. We fell right into the laid-back vibe and enjoyed a low key, beachside getaway.

Shops For Mom:

John’s Pass Village 

Full of boutiques and shops, this is a haven for water-side browsing. I picked up a pearl necklace and a handful of puka shell braided bracelets, along with an adorably kitschy ‘Madeira Beach’ hoodie. My boys didn’t last long shopping (surprise, surprise), but our condo was close enough for my husband to walk them back and let me keep rolling.

Tip: Booking a rental within walking distance will help you avoid parking, which depending on the time of day, looked pretty dicey, especially on the weekend.

Lori’s Soap and Sponge Market

I love homemade soaps and enjoy bringing them back as souvenirs from vacations. This shop had a plethora of scents, shapes and colors to choose from, and the service was friendly and more than excited to tell us about their products. I picked up a few goat milk bars and love them!

Boys Will Love:

Yankee’s Spring Training Game: Tampa, Florida

For baseball fans of all ages, tickets to a spring training game is the perfect way to enjoy watching the Yankees before the regular season. Make sure to give yourself plenty of time to get there. Tampa is 45 minutes to an hour from Madeira Beach, but depending on the traffic, could take you an extra 30 minutes on top of that (like it did us).

For the Whole Family:

Madeira Beach

Clean, wide-open and dotted with shells to scavenge, Madeira Beach is beautiful. My boys spent hours sifting sand and splashing away. Nothing beats the beach. Nothing.

Dolphin Quest

We enjoyed this relaxing, easy-going and informative cruise in a covered catamaran. We would’ve been excited to see just one dolphin, but were pleasantly surprised to see a whole bunch of them, swimming alongside the boat for the majority of the ride.The crew kept us entertained with facts and details about the dolphins, which they knew by name. The boat conveniently departs from the dock at John’s Pass.

Restaurants, Ice Cream & Coffee:

Sea Dog Brewing Company - Treasure Island

A few minutes down the road from Madeira Beach, Sea Dog Brewing Company serves fresh seafood and pub food overlooking the water. There’s an arcade on the second floor that my boys loved, too. Enjoy your food and let the kiddos entertain themselves. Brilliant!

Llama Java

Located in the heart of John’s Pass, Llama Java is the best place to grab a coffee, donut and egg sandwich before hitting the beach. We hit this place up every day and were met with friendly staff and delicious food and coffee every time.

Sip and Scoop

A tasty and conveniently located ice cream shop in John’s Pass. Energize the family with some sugar and buy yourself some more time to browse shell-dotted picture frames. They also have sandwiches, smoothies and coffee if you’re looking for something more substantial.

Thanks for coming along with me, the only girl on the trip. We're already dreaming of our next adventure, and I’d love to hear from other moms traveling with boys — where do you recommend? Drop a comment and subscribe to come along on our next trip!