City of Anna Maria
The Laid-Back Charm of Anna Maria
What truly sets Anna Maria Island apart is its timeless, laid-back charm. Unlike other crowded Florida destinations filled with high-rises and noise, Anna Maria feels like a step back in time — quiet streets lined with pastel-colored cottages, friendly locals, and a pace that invites you to slow down and savor the moment.
Take a scenic ride on the free island trolley to explore hidden gems and local shops.
Stroll along Pine Avenue, known for its boutique stores and art galleries.
End the day with a cocktail in hand while watching one of the island’s famous Gulf sunsets.
For tips on exploring like a local, visit our Anna Maria Island Guide.
Visit the Once Upon A Beach Office
Located in the heart of the City of Anna Maria, our office is more than just a check-in spot — it’s your island hub for all things vacation. Stop in to meet our friendly team, get local tips, and make the most of your stay.
Shop Our Bookstore & Gift Shop
Browse our coastal-inspired bookstore and boutique gift shop, perfect for finding your next beach read or picking up unique island souvenirs to take home.
Explore the Island in Style
Guests staying with us receive an exclusive 15% discount on 4- or 6-passenger golf cart rentals, making it easy to explore Anna Maria Island at your own pace — from quiet beach streets to your favorite local hotspots.
Top Dining Experiences
Anna Maria Island is not only famous for its pristine white-sand beaches and charming small-town vibe, but also for its incredible dining scene and authentic island experiences. Whether you’re planning a quick weekend getaway or a long vacation, Anna Maria offers something for everyone — from world-class seafood to unforgettable sunsets.
If you’re a foodie, you’ll love the local restaurants on Anna Maria Island that perfectly capture the essence of coastal Florida cuisine.
The Sandbar Restaurant – A true island staple, this beachfront restaurant has been serving fresh, locally sourced seafood for decades. Sink your toes in the sand while enjoying their famous grouper sandwich, crab cakes, or the chef’s daily specials, all with an unbeatable view of the Gulf of Mexico sunsets.
The Waterfront Restaurant – The Waterfront offers an upscale yet laid-back atmosphere, with creative dishes like seared ahi tuna, lobster bisque, and unique craft cocktails. It’s the perfect spot for a romantic evening or a special celebration.
Ginny’s & Jane E’s Café and Gift Store – For a more quirky and casual vibe, this beloved café serves hearty breakfast plates, fresh pastries, and excellent coffee. Don’t forget to browse their unique gift shop filled with island-inspired treasures.
For a comprehensive dining guide, check out our blog post on Best Restaurants in Anna Maria Island
Fishing the Island
For outdoor enthusiasts, fishing on Anna Maria Island is an experience you won’t forget. This coastal paradise offers something for every level of angler, from relaxed inshore trips to thrilling deep-sea adventures.
Cast a line from one of the island’s charming piers, embark on a guided charter excursion, or explore the crystal-clear waters teeming with redfish, snook, tarpon, and grouper. With a variety of fishing experiences, Anna Maria Island delivers excitement, relaxation, and plenty of fresh catches for your cooler.
For a truly personalized experience, we recommend booking a trip with Johnny Mattay of Anna Maria Charters or Captain David White, a trusted local guide known for his insider knowledge and passion for the best fishing spots around the island.Anna Maria Island isn’t just a postcard-perfect beach destination—it’s an angler’s paradise. Whether you’re a seasoned pro or just starting out, the island promises unforgettable fishing adventures set against the backdrop of stunning coastal beauty.
Learn more about fishing on Anna Maria Island
Plan Your Stay
Whether you’re sipping coffee on your porch, biking to the local market, or soaking up the sun on the beach, you’ll quickly understand why visitors return year after year.
Make your trip unforgettable by booking one of our luxury vacation rentals. From cozy beachfront cottages to spacious family-friendly homes with private pools, we offer the perfect home base for your island adventure.
Anna Maria Island isn’t just a vacation destination — it’s an experience that stays with you. Come for the beaches and sunsets, stay for the community, cuisine, and charm, and leave with memories that will last a lifetime.
