My first visit to Anna Maria Island was in 2019 and we have returned every year after that — and once you go, you’ll understand why. It is an easy, quick flight right out of Rockford, IL to St. Pete’s and with a 30 minute car ride, we are on the island. It is quintessential laid back island vibes and we love it so much!

Little did I know Anna Maria Island is one of the best kept Florida secrets with seven miles of the most beautiful beaches you can find right on the Gulf of Mexico— it was also voted as #3 on Trip Advisors “Top 10 Islands in the US.”

Who knew? Certainly not me. Sidenote: Anna Maria Island would make a PERFECT girls trip as it is incredibly safe and you don’t even need to rent a car if you don’t want!

Traveling to Anna Maria Island:

The best place to fly into is Sarasota or St. Petes. Best thing to do is Uber to the island (about 40 mins)— we call a wonderful man named Michael (941)301-6045. Then you honestly don’t even need to rent a car for the rest of your trip.

Transportation around the island:

There’s a free trolly that runs up and down the entire island from 6am - 10pm starting on the North side at Anna Maria City Pier. It travels up and down the island every 20 minutes.
After 10pm, there’s a Monkey Bus which is also free (donations appreciated) and you can call them anywhere on the island to pick you up 1-941-565-6542. Runs from noon - 3am.
Rather than renting a car, you might want to rent a GEM car or golf cart —which is the preferred mode of transportation around the island. Or, consider renting a bike!

What’s the vibe on Anna Maria Island?

There are no commercial restaurants or fast food on the island — only mom + pop shops with ONE Publix grocery store. Charm level 100! But there is certainly night life and live music, but this is not a “party” island. This is a laid back, non-rowdy island vibe.

Best spots for live music on Anna Maria Island:

Additional info on live music and events schedule here.

Manatee Public Beach

Harry’s Grill & Bistro (great food, plus Hallelujah brunch Sundays 10-11:30)
Wicked Cantina (across from beach, mexican, large patio) their music schedule is found here.

Island Time (cafe lights, cozy, open air atmosphere) also great food! Music starts at 7pm most nights.
Freckled Fin (more of an irish pub feel) live music starting at 7 most nights and Karaoke mondays, trivia nights, etc.
Blue Marlin (nautical theme, covered deck) lots of seafood
Bridge Tender (casual dining with indoor/outdoor bars) music daily, bingo Tuesday, Thursday & Saturday 1-ish and Bar Poker Monday & Friday 4-ish. Across the street is the Drift Inn, their outside dockside bar which always has music!
Ugly Grouper (games outside, good vibe) music daily 12-3, 5-8
Swordfish Grill on Cortez

Things To Do ON Anna Maria:

Well, besides the multiple beaches, great restaurants and live music everywhere, here are some additional things:

The best shopping is around Pine Ave or Bridge street with lots of restaurants, dessert shops, jewelry stores, boutiques, art galleries, and gift shops. It is located in close proximity to Anna Maria City Pier, Bayfront Park and the Rod and Reel Pier. Bridge street is another good spot for eclectic shops (also where to find the most nightlife)!
Best fishing opportunities are at the historical Anna Maria City Pier and Rod and Reel Pier. BONUS: there is an old Florida style restaurant at the end of Rod and Reel Pier where you can eat literally over the water.
Take a world famous dolphin tour — you can choose a kayak or canoe tour, paddle boat, or boat tour. All of these tours are family friendly, including the kayak tours where parents can bring young children along in 2 person tandem kayaks.
For guided tours, kayak, bike, and beach rentals — check out Anna Maria Island Excursions.

Visiting the Beaches:

There are three main public beaches on Anna Maria Island with excellent facilities, rentals, and concessions able to accomodate families:

Bayfront Park (northern tip)
Manatee Public Beach (center of island in Holmes Beach)
Coquina Beach (southern tip) also stop by the nearby Coquina Baywalk
Bean Point (tip of the island) if you’re not traveling with kids or looking for a more relaxed, less busy vibe — head to Bean Point — the furthest north point on Anna Maria Island and you can enter it at a crossroads on North Bay Blvd. and North Shore Dr.

Where to stay

Nothing is allowed over two stories on the island, so you will not find skyscrapers and resorts. Mostly, you’ll be looking for Airbnbs or other home rentals. A great place to check inventory is here: annamaria.com. Another option is the newer Waterline Marina Resort… all rentals are beautiful two bedroom suits. Be sure to book a year in advance for winter months! Also, I’ve been watching the renovations for the Joie Inn and it looks fab!

WHERE TO EAT ON ANNA MARIA iSLAND

I’m including a few of the tourist spots but also a good amount of hidden spots that you will probably not find recommended in other guides but are MUST STOPS in my opinion! Also, if you’re into seafood, you need to make the trek to Cortez Cafe. I hear they catch the fish and cook it up for you right there, but EWW! Not my vibe.

North Shore Cafe

The North Shore Cafe is relatively new to the island — and it’s gained quick popularity. Offering coffee, espresso, matcha, and various tea based beverages, they also have quite a few bites on the healthier side such as: avocado toast, acai bowls, smoothies, and sandwiches.

After discovering it, we found ourselves there daily.

They also have the cutest area in back for sitting and often have live music! You can also order wine and beer if you’re in the mood!

North Shore also added a shop with the worlds best gourmet popsicles. Try the Key Lime, Blood Orange Cheesecake, and Peanut Butter Pie.

THE DONUT EXPERIment:

Donut Experiment is a fun place to take kids, for sure. Delicious, design your own old fashioned donuts— but I highly recommend getting the specialty Key Lime!

If you’re looking for more baked goods, including desserts — check out Hometown Desserts, also located on Pine Ave by The Donut Experiment.

Paradise Cafe:

Located right inside a strip mall off Holmes Beach, this unassuming little cafe will blow your mind with their bagel breakfast sammies. Paradise Bagels & Cafe has been around for 25 years, making everything from scratch and serving up breakfast + lunch all year around! Pop in for a “New York style water bagel” sandwich (gluten free available) that will change your life!

MY REC: get the turkey & swiss. It sounds weird, but I PROMISE you, you’ll regret it if you don’t. It’s not lunch meat, it’s fresh carved and insanely delicious.

Cheesecake Cutie

Cheesecake Cutie is a great stop for breakfast, lunch, coffee or dessert! They have the most fantastic homemade, fluffy cheesecakes (they are individually sized), truffles, and amazing sandwiches and flatbreads!

Ginny & Jane E’s Cafe + Bakery

Ginny & Jane' E’s is some of the best breakfast on the island. It is ALWAYS busy and expect to wait a bit. The vibe inside is mix-matched furniture and eclectic goods for sale in their coastal shop.

The baked goods are just as fabulous — their cinnamon rolls are pretty legendary — and you really need to grab some to go!

Harry’s Grill & Bistro

First, you need to understand that Harry’s Bistro hosts a Hallelujah Brunch on Sundays from 10-11:30 and it’s everything. You donate what you can, fill out the breakfast menu, and he gives a heartfelt message.

But, they also have fantastic live music and food with happy hour daily from 3-5. Cute patio!

Isola Bella:

At Isola Bella, a Sicilian Italian restaurant, everything is homemade and you’re welcome. Freshly made pasta, imported Italian cheeses and organic produce really set this place apart. My friend loved the cannolis!

Two Scoops:

Located on the northern end of the island is Two Scoops — although many of the locals don’t prefer this because it’s a chain.

Gelato-Go

There are a zillion ice cream and gelato shops on the island, but this has become my favorite — for it’s cleanliness and also the lemon sorbet is fire! Find it on Bridge street.

Ugly Grouper:

Ugly Grouper is kind of a fun little casual stop. It’s outdoor seating only and has a lively atmosphere with bands, games, and some of the best grouper on the island.

They are known for their tacos that come in a crispy cheese shell. Worth a try, even if you just pop in for a beer!

SLIM’S PLACE:

Go directly to Slim’s Place, do not pass Go, do not collect $200. But be sure to order a Philly cheesesteak and don’t forget the WIZ. This is a homemade cheese sauce that you can’t live without, ok. Get it on the side if you’re not sure but GET IT. I also loved the Italian version called Pizza Steak (without wiz).

Also worth noting — I HATE seafood, and my brother force fed me the lobster mac + cheese, and I’m telling you what — order it!

THE SANDBAR:

For great sunset views, head to The Sandbar for food or drinks. With indoor and outdoor seating, you can sip on the world’s best piña colada with your toes in the sand while you watch the sun slip away into the Gulf of Mexico.

Vinny’s Italian Kitchen:

Vinny’s Italian Kitchen is takeout only. It’s a restaurant located inside an Italian market.

Let me tell you: the food is incredible. The pizza is very “Neapolitan” style — thin, with a bubbly crust. The pasta was off the charts — and enough for 3 meals. They actually have quite a few gluten free items!

MY REC: the fetuccini carbonara, and the porchetta (one of their specialities).

Wicked Cantina:

Located on Bradenton Beach, Wicked Cantina is a must stop if you’re looking for margaritas and queso… and who the heck isn’t? Seriously, the BEST queso. Always have live music.

Margaritas? Get em. Trust me.

Scott’s Deli (beach delivery):

Fantastic, freshly made deli sandwiches, delivered right to your beach umbrella. Scott’s Deli is a perfect lunch for a day of relaxing in the sun — gluten free options also available!

Waterfront Restaurant

Waterfront is going to be in the higher price range, FYI. Great appetizers and drinks — highly suggest the baked brie, truffle fries and fried queso. All of the food we tried was great — try to sit on the front patio with the breeze from the water for the best experience!

Beach House:

With a wonderfully chic, modern vibe, Beach House not only has some of the best food on the island, but it’s also got the best views. Get a spot outside and order everything on the menu. No really — I hear the seafood is amazing but I loved my burger and street corn!

Doctor’s Office:

For the ABSOLUTE. BEST. CRAFT. COCKTAILS on the island, head to the Doctor’s Office — which actually is, an old doctor’s office (originally the only one on the island). It’s dark. It’s cozy. Everything is freaking fantastic and handmade — even the nutmeg is freshly shaved to top off your drink. Trust me on the pineapple martini.

Anchor Inn

Anchor Inn is the most divey, local bar you could ask for. First, there’s still a cigarette vending machine?! I was taken aback that smoking is still allowed in Florida bars. I’ll be honest, if you have a hard time in smokey environments, this place isn’t for you. But it’s the only place open super late, so if you’re looking for an after hours — this is it. Go in, play some darts, and you’ll probably see Brad behind the bar wearing jean shorts with a cig hanging out of his mouth.

Daiquiri Deck

Although not a spot local to AMI, Daiquiri Deck will provide you one of the highest views on the island. Definitely worth a visit for a sunset!

Island Time

I mentioned this above under the best places for live music, but they really do have great food as well. Perfect relaxed island vibe with a great atmosphere!