Oh, Anna Maria Island, also referred to as AMI, how I love you. Shawn and I visited AMI for our first time in 2021 after friends of ours had told us we had to go. Well, it turns out that they were right – we would love it, so much in fact that we decided to plant some roots there and buy a home that we’ve been fortunate enough to spend every winter in since. Needless to say, I’ve spent my fair share [yet not enough] time in Anna Maria to *almost* consider myself a local pro when it comes to everything you need to know about the island.

It is truly such a gem, pure paradise, and a place of peace. The island is only 7 miles long and 1 mile wide, with the most beautiful, crystal clear water surrounding it. A few of my favorite things about the island:

• It’s not commercialized. In fact, there can’t be high rises on the island, so it mainly consists of all homes [lots of beautiful ones at that, which makes riding around the island a fun activity in itself].

• Chains aren’t allowed on the island, meaning everything there is a locally owned small business.
• It has an “old Florida” charm – it’s not too fancy [not fancy at all, really] and you can be super casual all day long. It’s amazing how little I wear makeup nor dress up when I’m on the island – just like paradise is supposed to be in my opinion!
• While it is a small island, it isn’t lacking in anything. You’ll see just from the dining options below that it has plenty to enjoy! You can make your trips here as busy or as quiet as you want them to be!
• The location – located on the Gulf of Mexico, the beaches are some of the best, while being just a 30-60 minute drive from some awesome off-island locations! More on those below!
• The ease of getting around the island. I love that once we are “home”, we are rarely in a car. It is a golf cart-friendly community and that’s really our only mode of transportation while we are there. Truly, the best!

There is so much more I love about the island, most of which you’ll see below! I’d love to hear more of your “must-do’s” when traveling to AMI – be sure to join our LIY Travels group and join in the hundreds of discussions on this topic there!

Let’s jump in — first things first, how to get to Anna Maria Island!

Getting To + From Anna Maria

There are 3 airports all within an hour or so distance from the island — here are my preferred ways of traveling to/from:

Sarasota Airport [SRQ]: Located just 30 minutes away! We always fly direct via Allegiant Air! Southwest Airlines is another great option to/from this airport!

Tampa/St Petersburg [PIE]: Another small airport that is a little less than an hour from AMI! Allegiant also flies direct to/from this airport for an inexpensive way to get there!

Tampa International [TPA]: Only one hour away from Anna Maria, this major airport is another great option to ensure travel to + from!

Once at the airport of your choice, you have a few options on how to get to the island — Rent a car, Uber, or use a trusted driver for airport pick up and drop off [we love to use TommyCar]!

Where to Stay on Anna Maria Island

Before I jump into where to stay, let’s talk about the 3 cities of the island:

Cities of Anna Maria Island:

Anna Maria: Located on the north tip of the island! This area feels like the newest, most “modern” part of the island! Great beach, fun restaurants, and great shopping on Pine Ave!

Holmes Beach: Centrally located on the island, we spend the majority of our time here along with Anna Maria! There are great beaches, restaurants, and shops in Holmes Beach!

Bradenton Beach: The southern part of AMI, this area is the most touristy to me. We’ve never stayed in Bradenton as it feels a little older to me, however, it does have Bridge St which is full of shops and restaurants!

Keep in mind, that while there are 3 cities on the island, the island is small so you’re never too far from any area no matter where you stay!

House Rentals:

Before buying a home, we rented different homes on the island several times to stay for a week. We love this option as you have your own kitchen to cook in, a private pool to lounge in, etc! You can use AirBNB, VRBO, or a few we’ve used: Anna Maria Vacations and AMI Locals!

Where We Have Personally Stayed:

Blissful Paradise: Located between Anna Maria and Holmes Beach, this is a beautiful, modern and new home! We loved everything about it – from the pool and hot tub to gorgeous decor and short golf cart ride to the beach!

The Blue Crab: This was the first home we stayed in when visiting AMI and absolutely loved it! It’s beautiful, great amenities, and nice quiet location! We could walk to the beach which was really nice!

Feelin’ Salty: This is a smaller home that Shawn and I stayed in when it was just him + I staying. This is more in the Northern part of the island, Anna Maria. It is an older home that has been renovated – not as warm and inviting as the others above, but still nice if you’re looking for something smaller!

LIY Team Suggestions:

Life’s A Beach Bungalow – Katy here from Team LIY! My husband and I stayed at this cute duplex with our then 14 month old and it was perfect for us! They had a pack n play and high chair in the unit as well as an umbrella, wagon, and beach chairs available for use as well! Super easy and quick walking distance to the beach!

Hotels/Resorts:

Erin’s Suggestions:

Bali Hai Beach Resort: We have stayed here along with some friends and we’ve all had a great experience! Located right on the beach, they do have updated rooms [facing the pool] that are nice and large! Bonus: They do have a small spa that you can get massages or other treatments done here! They do have a little lounge that you can order cocktails, breakfast, lunch, etc from!

Anna Maria Beach Resort: We have also stayed here and again, loved it! The rooms are updated and so warm and welcoming. We loved that we could walk right out from our patio onto the beach. Great central location on the island in Holmes Beach! I also appreciated that they had a hot tub along with a pool!

Joie Inn: I’ve never stayed here, but I can confirm that it is a charming, adorable little spot located across from the beach in Holmes Beach!

Waterline Villas & Marina: A luxury hotel located in Holmes Beach, this sits on the water, has a great restaurant, pool, and is the home of many different tours that you can do!

Mello on The Beach: While we’ve never stayed here, I’ve been eyeing this new resort as it’s been renovated! It looks like a fun vibe and sits right on the water which is nice! Centrally located in Holmes Beach!

Compass Hotel by Margaritaville: We have stayed here plenty of times – it’s right across the bridge off Anna Maria Island but only a few minutes away from getting onto AMI! It’s a fun spot that sits on a marina and has a fun restaurant, pool, and free breakfast every morning!

Team Suggestions:
Four Winds Beach Resort [off the island in Longboat Key] – It’s not the fanciest place, but it’s clean, a great price, and right on the beach!

Transportation Around Anna Maria Island

Getting around AMI is easy [and fun]! Being that it is only 7 miles long, you can easily get all around the island no matter what your preferred mode of transportation is! Here are my suggestions:

Golf Cart: My favorite way to ride around the island! We have used Fun & More to rent from [they drop off and pick up wherever you are staying], however, there are a lot of great options on the island to rent from!

Rent a Moke: These are so fun to have when on the island! Beach Bums is a great place to rent these from!

Car Rental: If you’d like a car [I would advise if you plan on traveling off the island for any activities], you can either rent from the airport or use Turo!

Bicycles: Another favorite way to take in the island: bicycles! Some house rentals and resorts will offer bicycles for free! If not, we’ve also used Fun & More for bike rentals! I love pedaling down all of the streets of the island to look at all of the houses!

The Monkey Bus: For only $5 per person, the Monkey Bus will pick you up wherever you are and drop you off wherever you want to go on the island [they will even do some off-island drop-offs!] Think party bus: loud music, disco lights, but a lot of fun! This is our preferred method of transportation with friends in the evening! You just dial ’em up and they are at your service! Note: You do have a wait sometimes so I’d recommend calling a little bit before your preferred departure time!

Island Trolley: The trolley runs from 6 am – 10:30 pm and covers the entire island! There are 35 trolley pickup spots on the island making it very easy to get on and off! It is free and easy to use! A very nice service the island offers!

Gulf Islands Ferry: This is a new ferry service that will now take you to/from Anna Maria and the city of Bradenton [note: Bradenton Beach is on the island, Bradenton is a separate off-island city]! It’s only $4-$10 per ride and avoids having to deal with heavy traffic on/off the island!

Best Time To Visit Anna Maria Island

Coconut from AMI Coconuts

While I personally don’t think there is ever a bad time to visit the island, there are definitely times that are less crowded than others and slightly more optimal weather!

If you are able to travel anytime, I would choose either after spring break and before school is out for summer break [middle of April through early June] OR anytime after Labor Day through Thanksgiving!

Spring Break [March/early April] seems to be the busiest time and the summer months are going to be h-o-t! We are typically there January through April and it’s lovely! You may experience some cooler days in December, January, February, but you also have a lot of beautiful days as well! October is known to be the best month on the island – weather is still gorgeous but a little cooler, it’s less crowded, etc!

Now, let’s get to the fun stuff —

Where To Eat

Breakfast:

Erin’s Favorites:

Ginny & Jane E’s Cafe [Anna Maria]: The first place we take any guests! This is such a fun, eclectic spot and has the best breakfast food – from creme brulee french toast, to delicious hashbrown casserole and you have to get the famous cinnamon rolls! Another favorite: pineapple mimosas!

Blueberries Cafe [Holmes Beach]: If you want the best Acai Bowl on the island, go here.

Donut Experiment [Anna Maria]: A fun one for kids! You can have donuts made to your liking! Pro Tip: order online and pickup or you may find yourself waiting in line for a while!

North Shore Cafe [Anna Maria]: It’s not a trip to AMI without a stop at North Shore Cafe! Also known for their acai bowls, they also have great coffee, smoothies, and toast! It’s such a fun vibe that sits on a channel! Pull up an adirondack chair next to the water and relax! Pro Tip: Try one of their popsicles in their pop shop! They also have the best merch! Sweatshirts, hats, tees — we have it [and love ’em all!]

Breakfast at Victoria’s [Holmes Beach]: If you like pancakes, this place is a must! The most dense pancakes on the planet!

Anna Maria Island Coffee Shack [Holmes Beach]: This is a newer spot, but where Shawn and I love to go get coffee and breakfast sandwiches for a quick bite!

A Few Other Suggestions:

Minnie’s Cafe [Holmes Beach]

Madomoseille French Cafe [Anna Maria]

La Creperie [Holmes Beach]

Lunch:

Erin’s Favorites:

Poppo’s Taqueria [Anna Maria]: If you like tacos, go here stat! Think Chipotle, only better in my opinion! Pro Tip: Don’t skip out on the chips + salsa, best chips I’ve ever had!

Scott’s Deli [Holmes Beach]: For the best sandwiches on the island, this little deli in Holmes Beach is a must! They have sandwiches, hot dogs, and tacos! You won’t be disappointed! Pro Tip: You can order and they will deliver to you at the beach!

The Cheesecake Cutie & Cafe [Holmes Beach]: Another favorite! I love their sandwiches [great chicken salad] and their mini cheesecakes, I dream about these things!

Graze Street AMI [Holmes Beach]: I visit this place way too often. Chef driven, they have weekly specials that are delicious! I love to get their chicken salad box but have heard their sandwiches are also amazing! Pro Tip: Buy their everything chocolate chip cookies, best cookies I’ve ever had! This is also my go-to place for charcuterie!

The Sandbar [Anna Maria – Waterfront]: If you’re wanting a place to eat on the beach, this is the spot! Pull up a chair in the sand and enjoy! This is a fun place to walk to from the beach if you’re spending the day in the sun!

The Porch [Anna Maria]: Lunch or dinner, you can’t go wrong! They have amazing salads for a light lunch! Pair it with sangria and you’re set!

Skinny’s Place [Holmes Beach]: If you’re looking for a great burger + fries, go here. It’s such a chill vibe and so tasty!

Whitney’s [Longboat Key]: If you’re venturing off island, Whitney’s is such a cool spot and atmosphere! Great food in a fun setting!

A Other Suggestions:

Grub Tropical BBQ [Anna Maria]

Pizzano’s Pizza [Holmes Beach]: For a slice of pizza!
The Old Salty Dog [Sarasota]

Dinner:

Erin’s Favorites:

Anna Maria City:

The Porch: Mentioned above for lunch, this is an awesome spot for dinner as well! While it’s not on the water, you can dine outside in their adorable porch and the food is fantastic. Shawn and I have had some of our best dinners on the island here! **Reservations are taken here!

The Waterfront: Another local favorite for quality food, this sits across from the bay, so you do have a great view of the water while being able to eat delicious food! Their truffle mac and cheese is the best!

The Sandbar: Mentioned above under lunch, a great beachfront dining option!

Rod & Reel Pier: One of [if not, the] oldest restaurant on the island. I love waiting to eat here as you typically see dolphins or manatees swim by. If you love seafood, you should be happy here!

Ocean Star Japanese and Sushi: This is probably where we ate the most last winter [I blame pregnancy]. Located on a marina, it’s a great little view and has delicious sushi and hibachi! **Reservations are taken here!

Pizza Social: If you’re looking for pizza takeout, this is a popular spot to order from! Pro Tip: The Feast in Holmes Beach has better pizza in my opinion, but this is still tasty!

Holmes Beach Restaurants:

The Feast: A hidden gem on the island. It’s tucked away in a strip mall and while it doesn’t look like much from the outside, the food is delightful. They are also known for their pizza so remember that for a great pizza takeout option! Pro Tip: Don’t sleep on their chicken strips with homemade ranch. It got me through pregnancy 😉

The Chateau Anna Maria: Located inside The Waterline hotel, this is a fancy little place to eat with really great food! **Reservations are taken here!

Hurricane Hanks: Another “don’t judge a book by its cover” type of place. This is a local’s favorite and it has great food! We love to eat here!

Beach Bistro [waterfront]: The finest dining experience on the island. You can eat directly on the beach and it is a 5 course menu. We ate here once and the food was everything I hoped it would be and more. The bill was as well 😉 If you’re celebrating something special, consider giving this a try but don’t say I didn’t warn you on the price – you will spend several hundreds of dollars. **Reservations are taken here!

The Ugly Grouper: This is my niece’s and nephew’s favorite spot as it has a lot of fun games for them to play while you wait! They have live music daily and while the food is average in my opinion, they are known for their grouper tacos!

Isola Bella Italian Eatery: If you like Italian, I trust that you’ll like eating here! **Reservations are taken here!

Topsail Steamer [Take & Make Seafood Boils]: Such a fun option for staying in but having an experience! They give you the giant pot along with the food of your choice and you can have your own seafood boil at home!

Vinny’s Italian Kitchen: We love this option for their take and bake options! Their lasagna is so good [along with their garlic bread]! It’s a great way to feed a lot of people for not a ton of money!

Bradenton Beach Restaurants:

Blue Marlin: While this is an expensive option [probably one of the most expensive on the island], it is delicious! Located on Bridge St, it also has a fun little outdoor bar area that you can get a drink at and listen to live music! **Reservations are taken here!

Beach House Waterfront: Located in Bradenton Beach, this place has an awesome atmosphere right on the beach. Sometimes the food is hit or miss, but we do like to take friends for the vibe!

Bridge St Bistro: Located on top of Island Time, it’s a great spot to watch the sunset while you dine! The food is great as well! **Reservations are taken here!

SALT Bar & Table: This is a newer restaurant, and while it is on the pricier side, we’ve really enjoyed our food here! Fun, modern environment and outdoor seating available! **Reservations are taken here!

Longboat Key Restaurants [Located just 10 Minutes Off-Island]

Mar Vista: One of our very favorite restaurants to eat at – we frequent this spot anytime we have guests in town! I love sitting under the button trees [it’s so dreamy] and the food is fantastic! Pro Tip: If you have a wait, walk next door to Shore for a cocktail! It’s such a cool vibe and has a fun shop to spend some time in! Another tip: Order the tator tots appetizer at Mar Vista!

Shore: I love the vibe of this restuarant so much. You feel like you’re in Miami or somewhere like this. Located directly on the water, it has a modern feel and a really great shop! Fun spot! **Reservations are taken here!

Dry Dock: A local’s favorite – this is also right on the water and has wonderful food! **Reservations are taken here!

Harry’s Continental Kitchen: Another great spot on Longboat, it is pricey, but the meal we had there was really delicious! **Reservations are taken here!

Drift Kitchen & Bar [Lido Key]

Cortez Options [Located Just 5 Minutes Off-Island]

Tide Tables: This became a favorite in the last year! It is super casual but a great place to eat right on the water [we’ve seen dolphins there every time] and the food has been great! If you’re not a seafood fan, I love their ribs!

Star Fish Company – We [Katy here] loved purchasing fresh fish to grill at our rental [cash only]! The prices were great and the tips on how to cook the fish were top notch. They also have a dockside restaurant if you prefer to go that route!

Bars and Cocktails:

Erin’s Favorites:

The Doctor’s Office [Holmes Beach]: The cutest place to get a cocktail on the island in my opinion. I love their garden area where you can dine [they even provide blankets at every chair when it’s cooler]! They serve a complimentary dose of “medicine” [aka that day’s shot] in a tea cup when you get sat and they have some really fun and delicious drinks! I’ve also heard it’s a great place to eat, but I haven’t tried it yet! **Reservations are taken here!

Bamboo Island Bar [Bradenton Beach]: Another personal favorite, we always go here with friends after we put our name in at the Beach House restaurant [within walking distance]! Located on Bridge St upstairs, we love to sit at the bar and chat it up with their bartender who is so fun! They make some delicious [and strong] drinks! Pro Tip: Order the fondue as an app!

Island Time [Bradenton Beach]: A late night fave – if you’re in the mood to listen to a band, dance a little, and have some drinks under a million twinkly lights, this is your place!

City Pier Grill [Anna Maria]: We love to walk out on the end of the City Pier to have a drink here [especially when we put our name in at Waterfront for dinner]! They often have live music and you may see people dancing which is fun! Another great spot to watch dolphins while having a glass of wine or beer!

Other Suggestions:
The Kokonut Hut [Bradenton Beach]

Daiquri Deck [Bradenton Beach]

Freckled Fin Irish Pub [Holmes Beach]

Ice Cream on Anna Maria Island:

Erin’s Favorites:

Dips Ice Cream [Anna Maria]: I love visiting this charming little ice cream shop! The atmosphere outside is really cute with the lights at night and inside you can find all of your favorite vintage candy! Bonus: Their ice cream is really good too!

Frosty Oasis [Holmes Beach]: This is our newest favorite ice cream place. Their ice cream in our opinion is the best on the island [and believe us, we’ve tried a lot]. Pro Tip: If you like peanut butter, order the triple peanut butter!

Small Town Creamery [Holmes Beach]: This was our favorite before Frosty Oasis came into play, but is still a really great option! They have a TON of flavors and we’ve liked ’em all! Toasted Coconut is a favorite here!

Two Scoops [Anna Maria]: This is a good spot to get some ice cream and then walk across the street to the city pier!

Anna Maria Island Creamery [Anna Maria]: If you prefer gelato, stop here!

What To Do on Anna Maria Island:

Erin’s Favorites:

Go To The Beach: You can’t beat the beaches in Anna Maria! Pro Tip: For the best beach day, hire Beach Suites to set-up a spot for you! We’ve done this a few times with friends and it’s awesome. They set everything up [complete with chairs, umbrellas, blankets, games, cooler, speaker, water, etc] and tear it down for you at the end of the day! All you have to do is show up!

Bean Point: Located at the Northern tip of the island, it’s where the gulf and the bay come together. I love to walk the beach at this area or watch the sunset here!

Guided Dolphin Tour: We did this with our family and had the best time! We were able to see so many dolphins along with manatees! We learned a lot and loved just being out on the water! We booked with AMI Dolphin Tours and they were great!

Fishing Charter:

Play Pickleball: There are great courts located in Holmes Beach behind the fire department! Note: There is also a playground next door along with a dog park should you have children or pets 🙂

Get a Massage: I’ve only gotten a massage at Bali Hai and it was great!

Walk City Pier: This is a great spot to spot marine life: dolphins, manatees, fish, etc!

Jet Ski Rentals:

Sunset Boat Cruise: We did this once with friends and would totally do it again! It’s a great way to catch the sunset on the water while enjoying some champagne and charcuterie on a really cute pontoon boat! We used Captain Sky Cruises!

See a Show at Island Players Theater: If there is a show playing while you’re there and you love theater, it is something fun and different to do!

Have a Beach Picnic: We did this once and it was so cute! If you’re celebrating something special, consider doing this for a fun way to watch the sunset! We used Posh Picnic and it was great!

Family or Maternity Photoshoot: If you’re looking for a local photographer to shoot with, I’ve worked with Everence Photography and absolutely love Jessica!

Miniature Golf: There is a small mini golf course on Bridge St [Fish Hole] should you like to get a round in with the family!

C Ponies Horseback Riding

Where To Shop on Anna Maria Island:

Erin’s Favorites:

Anna Maria:

The Shiny Fish Emporium: This is such a fun and special store! Ages of all will love it! Pro Tip: Paint a sand dollar here! It’s a fun activity to do with kids!

Pink & Navy: Women’s + men’s apparel – a trendy store full of cute items!

Pineapple Marketplace: This has several different vendors inside [think flea market almost] but I always walk away with something fun!

Island Cabana: They carry some personal favorite brands [ie: Liverpool] and also have the cutest kids clothes!

AMI Outfitters: A great spot to shop for your guy! Great quality brands!

Nomad: A little on the expensive side, but fun to look around!

Holmes Beach:

Original Sand Dollar: My favorite store on the island, you can find a little bit of everything here! Decor, fashion, accessories, etc!

Sun & Surf Beach Shop: Think your traditional surf shop but better.

Vintage Beach: My mom’s favorite store on the island! They carry so many great neutral and easy to wear pieces! Z Supply and other great brands are carried here!

Bradenton Beach:

Bridge St: Take a stroll on Bridge St for lots of fun little shops to pop into!

Fox Mercantile [Cortez]: Just 5 minutes off the island, it’s definitely worth a visit! It’s such a cute spot and they have some fun home decor, accessories, and a great little coffee shop inside!

Where to Get Groceries on Anna Maria Island:

Publix: Gosh, I love Publix. Their BOGO deals are the best! Pro Tip: Their BOGO’s change every Thursday!

Farmer’s Market: Every Tuesday at City Pier Park on Pine Ave!

Olive Oil Outpost: A great spot to buy fresh bread, artisanal cheeses, olives, etc!

Pro Tip: You can also InstaCart several different options off-island: Aldi, Walmart, Etc!

Off Island Favorites

Erin’s Favorites:

University Town Center [Sarasota]: The mall of all malls. Located around 45 minutes from AMI, we love to go here for a day or evening. The indoor mall has all of the best stores and then there are a lot of shops and awesome restaurants outside as well! It’s a really nice place to walk around and just take it all in!

PopStroke [University Town Center, Sarasota]: Think TopGolf, but in miniature golf form. This is Tiger Wood’s miniature golf course and it’s so fun! Have drinks + food while you play!

Ranch Nights [Lakewood Ranch]: Every Wednesday evening during October through May. We love to go for live music, tons of food trucks, watch the Corn Hole tournament, and eat at some of their great restaurants here!

St Armand’s Circle: A great place to shop and eat! It’s fun to walk around and spend an afternoon! Located around 30-40 minutes from AMI.

Ringling Museum [Sarasota]: This is worth visiting simply for the grounds! It is stunning! It is also interesting to tour the Ringling Museum to learn about the history of the Ringling Circus!

Mote Aquarium [Sarasota]: If you have children and need a fun activity to do indoors, this is a great option! Pro Tip: Once done, walk across the street and eat lunch or dinner at The Old Salty Dog!

Busch Gardens [Tampa Bay]: Again, if you have children and are looking for something different to do, visit Busch Gardens [approx 1 hour away] for a day at an amusement park!

Top Golf [St Pete & Tampa]: Two locations within an hour or so!

Siesta Key Village: A great place to visit for fun places to eat and shop!

Team Suggestions:

Treeumph! Adventure Course [Bradenton]:

Don’t forget to join us over at LIY Travels for even more AMI Tips + Suggestions!