Anna Maria Island (AMI) is a seven-mile barrier island on Florida’s Gulf Coast, prized for sugar-soft sand, teal water, and a resolutely Old-Florida vibe—no high-rises, just pastel cottages and sea oats. Settled in the late 1800s, the island grew around fishing piers and boatyards; today, you’ll still see pelicans perched on dock pilings and skiffs gliding across Bimini Bay at dawn.

Beyond the beaches—Bean Point, Manatee Public Beach, and Coquina—expect breezy bike rides, dolphin-spotting cruises, and easy day eats: grouper sandwiches, stone crab (in season), and key lime pie. Stroll Pine Avenue’s indie boutiques, then watch a fiery Gulf sunset drift into starlight. The free trolley ties it all together, making a car optional once you arrive.

Practical notes: Fly into Sarasota–Bradenton (SRQ; ~30 minutes) or Tampa (TPA; ~1 hour), rent a bike or golf cart, and ride the free AMI trolley end-to-end. Spring and fall bring mild weather; summer is warm and dreamy with afternoon showers. During May–October sea turtle nesting, use red-filter lights and keep beaches dark and clean.

Anna Maria Island

Shaped by sea breezes and slow mornings, AMI is really three little towns—Anna Maria (north end), Holmes Beach (middle), and Bradenton Beach (south end). Each has its own rhythm: pine-shaded lanes near Bean Point, lively Bridge Street with its old pier and mini golf, and wide beaches made for long, barefoot walks.

• Top sights: Bean Point for quiet sunrise and sunset, the historic Anna Maria City Pier, Coquina Beach and its Baywalk, Leffis Key Preserve overlooks, and the shops and murals around Bridge Street.
• Signature experiences: Dolphin cruise from Bradenton Beach Marina, parasailing off the Gulf, kayak or SUP through mangroves near Bimini Bay or Robinson Preserve, and night stargazing on the sand.
• Where to eat: Pier-side classics (Rod & Reel Pier), toes-in-the-sand dining (The Sandbar), a special-occasion splurge (Beach Bistro), and unfussy standouts (Ugly Grouper, Tide Tables and Star Fish Company just over the Cortez Bridge).

Where to stay: For beachfront condos and pastel cottages, browse VRBO on Anna Maria Island and compare hotels and inns on Hotels.com for Anna Maria Island. North-end cottages near Bean Point are serene; Holmes Beach offers central access; Bradenton Beach puts you steps from Bridge Street nightlife.

How to get there: Fly into SRQ (often $120–$350 round-trip domestically) or TPA ($150–$400), then drive 30–70 minutes. Start your search with Trip.com flights. Once on-island, the free AMI trolley runs roughly every 20–30 minutes from Coquina Beach to the City Pier.

Day 1: North-End Welcome, Pine Avenue, and a Bean Point Sunset

Morning: Travel day. If you’re flying, aim for a late-morning arrival at SRQ or mid-day at TPA; pick up a compact car. On the way in, grab picnic supplies—fresh fruit, chips, and deli salads—to maximize beach time later.

Afternoon: Check in and fuel up with coffee and a light bite at Ginny’s & Jane E’s (quirky café-bakery inside a vintage market; cinnamon rolls, pressed Cuban sandwiches). Explore Pine Avenue: stop at Olive Oil Outpost for picnic fixings, browse local art, and walk the Anna Maria City Pier to watch anglers reel in sheepshead and snook.

Evening: Head to Bean Point—the island’s quiet, dune-framed tip—for a spellbinding sunset where the Gulf meets Tampa Bay. Dine at The Sandbar Restaurant with your toes in the sand; order Gulf grouper (blackened if you like a little heat), local catch of the day, and a slice of key lime pie. Nightcap at The Doctor’s Office in Holmes Beach, a speakeasy-style bar known for serious craft cocktails (book or arrive early for seats).

Day 2: Kayaks, Dolphins, and Bridge Street After Dark

Morning: Grab iced lattes at Island Coffee Haus or an almond croissant at North Shore Café, then paddle. If you prefer calm water, book kayaks or SUPs for the mangrove edges of Bimini Bay or nearby Robinson Preserve (easy brackish trails; expect egrets, mullet schools, maybe an osprey). Rentals and guided eco-tours typically run $45–$75 per person for 2–3 hours.

Afternoon: Cross the Cortez Bridge for a dockside lunch. Tide Tables serves impeccably fresh mahi tacos and smoked fish dip; Star Fish Company (cash preferred) plates fried Gulf shrimp and hushpuppies in a working fish house atmosphere. Back on AMI, take a dolphin cruise from Bradenton Beach Marina—90 minutes of bottlenose dolphins surfing boat wakes, with commentary on local ecology ($35–$45 adults, often less for kids).

Evening: Wander Bridge Street for souvenirs and sunset photos on the old pier. Play a round at The Fish Hole mini golf under string lights, then choose dinner: upstairs at Bridge Street Bistro (pan-seared scallops, Gulf views), or casual beach-Mex at Wicked Cantina (birria tacos, house margaritas). Finish with a cone at Small Town Creamery or a brownie sundae at Two Scoops.

Day 3: Coquina Beach, Piers and Pelicans, and a Farewell Feast

Morning: Sunrise stroll along Coquina Beach, then pancake plates at the Anna Maria Island Beach Café on Manatee Public Beach (famous for all-you-can-eat pancakes—go early). Walk the Coquina Baywalk and Leffis Key Preserve boardwalks; climb the small overlook for a 360-degree sweep of mangroves, Sarasota Bay, and the Gulf.

Afternoon: Pack, then take an early lunch at the Rod & Reel Pier—a creaky wooden pier with grouper sandwiches, peel-and-eat shrimp, and pelicans practically posing for portraits. If time allows before your airport drive, rent bikes for a final cruise down Gulf Drive or pause at Manatee Public Beach for one last dip. Depart for SRQ (~30 minutes) or TPA (~60–75 minutes) in the early afternoon.

Evening: If your flight is later, slip in a last beachfront toast: the Kokonut Hut (at Gulf Drive Café) often has live music and toes-in-the-sand seating—an ideal coda to your island interlude.

Coffee, breakfast, and snacks to try: The Donut Experiment (build-your-own donuts), Minnie’s Beach Café (old-school diner; cash), Back Alley Treasures (espresso bar + local art) in Bradenton Beach.

Insider tips: The free AMI Trolley runs the island’s length; use it during peak parking hours. For beach shade, bring a lightweight pop-up; Gulf breezes can be brisk. Red tide occasionally blooms—ask locally or check advisories before water activities. Stone crab season (Oct–May) is a treat; soft-shell crab pops up in spring menus.

Where to Book and How to Get There

• Stay on the beach or bay: Compare cottages, condos, and pool homes on VRBO (Anna Maria Island) and hotels/inns on Hotels.com (Anna Maria Island).
• Flights: Check fares to SRQ and TPA on Trip.com, then pick up a car at the airport (a compact is easiest to park on-island).

Optional Viator Inspirations (outside Florida)

Love mangrove paddles and stargazing? These highly rated experiences capture a similar spirit—great to bookmark for future travels. Note: These tours are not located on Anna Maria Island.

• Kayaking Mangrove Adventure at Havelock

  

  Peaceful paddling through mangrove tunnels with birdlife all around—perfect for nature lovers who enjoyed AMI’s calm backwaters.

• Exploring the Skies with Newtonian Telescope

  

  If AMI’s dark-sky beach nights ignite your curiosity, this guided stargazing session is a wonderful add-on idea for a future island trip elsewhere.

Cost snapshot for 3 days (per adult, typical): Flights $150–$400; lodging $180–$450 per night (seasonal); kayak/SUP $45–$75; dolphin cruise $35–$45; parasailing $85–$110; restaurant meals $15–$35 entrées; free trolley and beach access.

In three unhurried days, you’ll taste Old Florida—quiet lanes, teal water, and meals where the day’s catch is the headliner. From Bean Point sunsets to Bridge Street nights, Anna Maria Island proves small places can hold big memories.