Every year, our Anna Maria Island NCAA Bracket Challenge brings together guests, friends, and basketball fans from all over—and 2026 was no exception. With upsets, buzzer-beaters, and unforgettable moments, this year’s tournament delivered excitement from start to finish.

And now, we’re excited to officially announce our 2026 winner.

Meet Our Champion: Caroline

This year’s winner, Caroline, is an accountant originally from Pittsburgh, Pennsylvania, now living in Buffalo, New York—proudly cheering on the Bills and always ready for her next travel adventure.

What makes this win even more meaningful is the story behind it.

Caroline’s love for college basketball started at a young age, thanks to her dad, who has always been a huge fan of the game. In fact, he was the one who introduced her to our bracket challenge—making this win feel just as much his as it is hers.

The Winning Strategy

Caroline kept things simple—and it paid off.

Instead of analyzing stats or following expert predictions, she trusted her instincts. Each matchup was decided based on gut feeling, without overthinking or second-guessing.

Her approach:

• No probabilities

• No outside input

• No second guesses

She made her picks, locked them in, and let the tournament unfold.

And this year, that strategy led her all the way to the top.

Let’s also give a round of applause to our top 10 finalists, who demonstrated their expertise and passion for college basketball:

A Reminder That Anyone Can Win

That’s the magic of March Madness.

You don’t need to be an expert or spend hours analyzing matchups. Sometimes, trusting your instincts is all it takes.

Caroline’s win is a perfect reminder that anyone can take home the title.

Looking Ahead

We’re incredibly grateful to everyone who participated in this year’s challenge and made it such a fun and engaging experience.

Congratulations again to Caroline on an amazing win—we hope you enjoy every moment of it.

And for everyone else, we’ll see you back for next year’s challenge.

Until then, we hope to welcome you to Anna Maria Island for some well-deserved relaxation, sunshine, and maybe even a little bracket planning for 2027.

About Dan’s Florida Condos on Anna Maria Island, Florida:

Anna Maria Island, Florida is located on the Gulf Beaches of Florida, just 50 minutes south of Tampa and 20 minutes from Sarasota.

The Island offers over seven miles of beautiful beaches to explore, along with award-winning beachside restaurants and laid-back tiki bars that make every day feel like vacation mode.

Dan’s Florida Condos features a curated collection of 1BR and 2BR vacation rentals across Anna Maria Island, including many standout options within the highly sought-after Runaway Bay community. Located directly across the street from the Gulf with private beach access, Runaway Bay is home to the island’s largest heated saltwater pool and a full lineup of resort-style amenities including tennis, pickleball, shuffleboard, bocce ball, and a scenic fishing pier.

Each of our condos is fully equipped with everything you need, from kitchen essentials to beach chairs and coolers, so you can settle in and start enjoying island life from the moment you arrive.