Personalized Anna Maria Island Vacations Start with a Perfect Match
Every vacation tells a story & on Anna Maria Island, yours begins here. ✨
At Once Upon A Beach, we call it your Vacation Personality — the way you naturally connect, unwind, and make memories. Discover whether you’re a Dreamer, Explorer, Gatherer, Creator, or Healer, and let us help you find the homes and island experiences that feel like they were made just for you.
Are you most at home drifting through sunrise light, chasing the day’s next adventure, gathering everyone around the table, creating something beautiful, or simply breathing deeper beside the sea?
Take the quiz to uncover your match — then let us guide you to the homes and island experiences that bring your story to life.
Your island awaits. Start the story here.
Gentle mornings, golden sunsets, and the sound of the tide calling you home.
You’re drawn to romance, reflection, and simple moments that linger long after you leave — the quiet coffee before the world wakes, the hush of the sea under a painted sky.
Find peace in ocean views and quiet spaces that feel like a deep exhale, where time stretches softly and your only task is to dream.
🧭 The Explorer
Your story is written in motion — discovering new paths, flavors, and hidden corners of the island.
Adventure fuels you, curiosity guides you, and every day brings something new to uncover.
Experience AMI through action, exploration, and vibrant connection. Every turn leads to a new story — a hidden path, a fresh horizon, and the thrill of discovering what waits beyond the next wave.
🐚 The Gatherer
You find joy where laughter echoes and memories are made together.
From family dinners to beach games, your story is about togetherness and belonging. Your story is told in laughter and shared sunsets — where connection feels like home.
Stay in homes designed for gathering — spaces made to hold your favorite people close and moments that become part of your family’s story.
🎨 The Creator
ChatGPT said:You see beauty everywhere — in the colors that shift with the tide, the textures that tell stories, and the way light dances across the water.
You see beauty everywhere — in the colors that shift with the tide, the textures that tell stories, and the way light dances across the water.
Your journey is one of inspiration and expression, where every moment becomes part of your masterpiece.
Stay in spaces that awaken your creativity and celebrate design, art, and the freedom to imagine.
💆 The Healer
You seek stillness, restoration, and meaningful moments of calm — the kind that linger long after the tide rolls out.
Your story is one of renewal — mind, body, and spirit. You are drawn to spaces that breathe, where sunlight filters through palms, waves whisper in the distance, and time itself seems to slow.
Let serenity meet you in quiet courtyards, peaceful pools, and sunlit solitude, where each day becomes an invitation to simply be — to rest, reflect, and reconnect with what matters most.
🌊 Find Your Island Match
Every vacation tells a story — discover yours.
Take the Vacation Personality Quiz to see whether you’re a
Dreamer, Explorer, Gatherer, Creator, or Healer —
and find the homes and island moments that fit you best.
