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.

Follow along so you don't miss the best of Florida.