Anna Maria Island, a barrier island on Florida’s Gulf Coast, is a slice of paradise known for its old-Florida charm, sugar-white sandy beaches, and laid-back vibes. Whether you’re planning a weekend getaway or a week-long retreat, having a well-planned itinerary helps you make the most of your stay. This article presents a detailed 1500-word itinerary for travelers looking to explore Anna Maria Island like a local.
Day 1: Arrival and Island Orientation
Morning: Welcome to Paradise
As soon as you arrive on Anna Maria Island, whether via car from the mainland or a short flight into nearby Sarasota or Tampa, take a moment to breathe in the ocean air. Settle into one of the charming beach cottages or boutique hotels like the Anna Maria Beach Resort or Waterline Villas & Marina.
Afternoon: Explore Pine Avenue
Head to Pine Avenue, the heart of Anna Maria. This walkable stretch is lined with cute shops, local art galleries, and cafes. Grab lunch at The Donut Experiment—where you can create your own fresh donut—and shop for beachwear at Island Cabana.
Evening: Sunset at Bean Point
Bean Point, located at the northern tip of the island, offers one of the most tranquil and picturesque beaches on the island. Bring a blanket and relax as the sun sets over the Gulf of Mexico. Dinner can be enjoyed at The Waterfront Restaurant, known for its fresh seafood and relaxing patio ambiance.
Day 2: Beach Day and Water Activities
Morning: Manatee Public Beach
Kick off your morning at Manatee Public Beach, which is great for families and first-time visitors. It offers ample parking, restrooms, and the Anna Maria Island Beach Café, where you can grab an all-you-can-eat pancake breakfast.
Afternoon: Kayaking and Paddleboarding
Rent a kayak or paddleboard and explore the crystal-clear waters of Bimini Bay or the mangrove tunnels of Robinson Preserve. You might spot manatees, dolphins, and a variety of native birds. Companies like Beach Bums Rentals offer affordable options.
Evening: Bridge Street Pier
Drive or take the free trolley to the southern end of the island and enjoy a walk along the historic Bridge Street Pier in Bradenton Beach. Grab dinner at Blue Marlin Grill or Anna Maria Oyster Bar on the pier. Don’t forget to grab a scoop of ice cream from Joe’s Eats and Sweets.
Day 3: Nature and Culture
Morning: Robinson Preserve
Just off the island, Robinson Preserve is a 487-acre nature preserve perfect for hiking, biking, and kayaking. The observation tower offers sweeping views of Tampa Bay and the Gulf. Don’t forget binoculars if you enjoy birdwatching.
Afternoon: Visit the Anna Maria Island Historical Museum
Learn about the island’s rich history at the Anna Maria Island Historical Society. The museum is located in a 1920s icehouse and includes exhibits about the island’s pioneer settlers and early development. Nearby, see the old city jail—great for quirky photo ops.
Evening: Live Music and Dining
Wrap up your day at The Sandbar Restaurant, which is right on the beach. Enjoy live music and a menu featuring sustainably sourced seafood. Don’t miss the grouper tacos and signature cocktails.
Day 4: Island-Hopping and Exploration
Morning: Egmont Key State Park
Take a guided boat tour or rent a private charter to visit Egmont Key, a small island accessible only by boat. It’s home to a historic lighthouse, a deserted fort, and incredible snorkeling opportunities.
Afternoon: Lunch and Shopping in Holmes Beach
Return to the island and grab a casual lunch at Skinny’s Place—a no-frills, classic Florida burger joint. Spend your afternoon browsing the shops in Holmes Beach, including Island Bazaar for beach gear and Olive Oil Outpost for gourmet snacks and wines.
Evening: Mini Golf and Fun
Head to The Fish Hole for some family-friendly mini-golf fun, then have dinner at Wicked Cantina or Sharky’s Seagrill. These places offer a relaxed vibe and plenty of options for kids and adults alike.
Day 5: Spa Day and Romance
Morning: Spa and Relaxation
Treat yourself to a massage or facial at Sea-renity Beach Spa & Eco Boutique. They even offer beachside massages under private tiki huts for an unforgettable experience.
Afternoon: Private Beach Time
Spend your afternoon lounging at Cortez Beach or Coquina Beach. These areas are less crowded and perfect for some quiet reading, sunbathing, or collecting shells.
Evening: Romantic Sunset Cruise
Book a sunset cruise with Paradise Boat Tours or Kathleen D. Sailing Catamarans. These tours offer scenic views of the Gulf as the sun dips below the horizon, often accompanied by complimentary champagne or snacks.
Day 6: Day Trip to Sarasota or St. Armands Circle
Morning: Sarasota Jungle Gardens
Take a short drive to Sarasota, where you can visit the Sarasota Jungle Gardens or the Marie Selby Botanical Gardens. These are great options for both couples and families.
Afternoon: Shopping at St. Armands Circle
Continue your day at St. Armands Circle, a historic shopping district offering upscale boutiques, gourmet restaurants, and galleries. Enjoy lunch at Columbia Restaurant, one of Florida’s oldest Spanish-Cuban restaurants.
Evening: Return to the Island
Head back to Anna Maria Island and relax with dinner at Rod & Reel Pier. This over-water restaurant offers a true “Old Florida” experience and some of the best fish and chips around.
Day 7: Farewell and Relaxation
Morning: Sunrise Walk
Take an early morning stroll along the beach before the crowds arrive. The soft waves and pink skies make for a peaceful start to the day.
Afternoon: Last-Minute Souvenirs
Use your final few hours to grab souvenirs from local shops like Shiny Fish Emporium or Ginny’s and Jane E’s at the Old IGA. The quirky interior and locally made goods are a hit with visitors.
Evening: Departure
Depending on your travel schedule, grab a final bite at Ginny’s or Anna Maria Island Beach Café before heading out. You’ll leave with sand in your shoes and memories to last a lifetime.
Bonus Tips for Your Anna Maria Island Itinerary
- Transportation: Use the free Island Trolley to get around easily without worrying about parking.
- Packing Tips: Bring sunscreen, a wide-brimmed hat, reusable water bottles, and flip-flops. Don’t forget a light sweater for breezy evenings.
- Wildlife Caution: Respect local wildlife—no feeding birds or disturbing turtle nests during nesting season.
- Local Laws: Alcohol and glass containers are generally prohibited on public beaches.
Conclusion
An Anna Maria Island itinerary offers the perfect blend of relaxation, adventure, and cultural immersion. From pristine beaches to historic piers and from gourmet seafood to charming boutiques, every corner of the island is filled with opportunities for unforgettable moments. Whether you’re traveling solo, as a couple, or with your family, planning ahead ensures your trip is smooth, enjoyable, and full of the best Anna Maria Island has to offer.
For more information, you can visit Anna Maria Island’s Wikipedia page.
