The Perfect Weekend on Anna Maria Island

Everything you need to eat, stay, and explore — straight from someone who's been there.

If you haven't been to Anna Maria Island yet, let me be the person who finally convinces you to go. This little barrier island off Florida's Gulf Coast is the kind of place that slows you way down — in the best possible way. No chain restaurants. No high-rises. Just local spots, beautiful beaches, and the kind of weekend that you will always remember and speaks to your soul. 

Here's exactly how we spent ours.

Where We Stayed: Anna Maria Island Bay View

We stayed at the Anna Maria Island Bay View vacation rental, and it genuinely delivered on its name. This was a gorgeous 4 bedroom 5.5 bath home with a pool and game room. Waking up to those bay views every morning set the tone for the whole trip. If you're visiting AMI, renting local is a must. It makes the whole experience feel like you actually live there, even if just for the weekend.  This property allowed us to bring our friends boat.  It is the perfect home for a big group, there were 8 of us that stayed and we were very comfortable.  We took out the boat in the morning and went to Jew Fish Key and Beer Can Island on the North end of Longboat Key.  It was neat to watch the sunrise off the dock and the sunset at the beach.  Lowtide was really neat off the dock because there was a bunch of starfish! You can view and rent this home here.

Morning Coffee: Back Alley Treasures

📍 108 Bridge St, Bradenton Beach 

Every great trip starts with a great cup of coffee, and Back Alley Treasures did not disappoint. Tucked away on Bridge Street, this place is half charming coffee bar, half boutique shop — and 100% a vibe. We pulled up first thing in the morning and it instantly set the mood for the whole day. The baristas clearly care about every single cup, and the atmosphere is the kind you want to sit in way longer than you have time for. Don't leave without grabbing a treat to go. You'll thank me later.

Lunch: Wicked Cantina

📍 101 7th St N, Bradenton Beach

For lunch we headed to Wicked Cantina, and this place is seriously fun. It's a Mexican-American spot with serious island energy — think fresh mahi mahi tacos, margaritas that hit the spot on a warm afternoon, and outdoor patio seating that makes you feel like you're on vacation even when you're already on vacation. If you go, grab a seat outside. The island breeze plus a good marg equals the best kind of afternoon. We were not in a rush to leave.

Dinner: The Ugly Grouper

📍 5704 Marina Dr, Holmes Beach 

Hands down our favorite dinner of the whole trip. The Ugly Grouper is the kind of place that becomes your personality by the end of the night. It's lively, fun, and the food is incredible — the grouper tacos alone are worth the trip to the island. There's live music, outdoor tables, lawn games, and strong drinks. We went for dinner and ended up staying way longer than planned because the vibe just wouldn't let us leave. 

Fancy Dinner and the BEST Dessert: The Porch Restaurant

📍 9707 Gulf Dr, Anna Maria | @theporchrestaurant_ami

I went in for dinner and left completely obsessed with the whole menu. The Porch is a gem — it's tucked into a charming converted house at the north end of the island and has this intimate, special-occasion feel without being stuffy. The food is thoughtful and seriously delicious (the salmon is life-changing), and don't even get me started on dessert. This one surprised me in the best way. Add it to the list, and make a reservation.

The Bottom Line

Anna Maria Island is one of those Florida spots that still feels like Florida used to feel — unhurried, local, and genuinely beautiful. Between the bay views from our rental, the coffee ritual at Back Alley Treasures, tacos at Wicked Cantina, fresh oysters on the pier, the most fun dinner of our trip at The Ugly Grouper, and that unforgettable meal at The Porch — this weekend had everything.

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The Beaches: Where to Plant Your Towel

Anna Maria Island has some of the most beautiful beaches on Florida's Gulf Coast, and knowing which beach to hit — and when — makes all the difference. Here's where we went and what you need to know before you go.

Bean Point — The Most Breathtaking Spot on the Island

If you only make it to one beach on Anna Maria Island, make it Bean Point. This is the northernmost tip of the island, and it genuinely took my breath away. The water meets the bay on one side and the Gulf on the other, and on a clear day it feels almost unreal the water and beach are that beautiful.

Here's the thing though: Bean Point is not the easiest beach to get to, and that's exactly what makes it so special. There's no parking lot — you park on the street, and spots are extremely limited. Most people walk or bike in from town. The reward for that little extra effort? A beach that feels like it's all yours. Even on a busy weekend, Bean Point has this peaceful, secluded quality that's hard to find anywhere else on the island.

It's perfect for a long walk along the shoreline or just laying out and soaking it all in — but do not swim here. The currents at the point are strong and unpredictable. Enjoy the beauty, keep your feet in the sand, and take about a thousand photos. You won't regret it.

Bradenton Beach — Lively, Accessible, and Classic Gulf Coast

For a more classic beach day, Bradenton Beach is your spot. Located on the southern end of Anna Maria Island along Gulf Drive, this stretch of white sand is gorgeous and a little more accessible than Bean Point — with street parking and metered lots nearby along Bridge Street and Gulf Drive. It still fills up fast on weekends, so arriving early is always the move.

The water here is that signature Gulf of Mexico turquoise-green, the waves are gentle, and the vibe is relaxed and friendly. It's a great choice if you want to swim, play in the water, or just spend a full afternoon with the sun on your face. You're also just a short walk from Bridge Street, so lunch or a post-beach margarita at Wicked Cantina is very much on the table.

The Piers: A Little Local History on the Water. 

Anna Maria Island has two iconic piers worth knowing about. The City Pier in Anna Maria sits at the north end of the island on the bay side — it's a beloved local landmark, great for fishing and watching the sunset over the water. Then there's the Bridge Street Pier in Bradenton Beach, which is right in the heart of the action on the south end of the island. This is where you'll find the Anna Maria Oyster Bar on the Pier nearby and all the charm of the Bridge Street corridor. Both piers are free to walk and worth a stroll — especially at golden hour. 🌅

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