Anna Maria Island Travel Guide: A Weekend in Florida's Most Charming Beach Town

It’s no secret that I love Florida. After spending 12 wonderful years growing up in the Sunshine State, it has officially etched a special place in my heart and even though I’ve traded palm trees for skyscrapers, I still jump at any opportunity to go back. This is why when I was given the chance to visit my favorite little beach town, Anna Maria Island, and spend a weekend of fitness focused activities in partnership with Visit Bradenton, I eagerly accepted.

If this is the first time you’ve heard of Anna Maria Island, prepare to be delighted. Situated on the west coast of Florida, just south of Tampa and north of Sarasota, lies a 7 mile stretch of sugar sand beaches, turquoise gulf water, family-owned restaurants and pastel houses. You won’t find any high-rise condominiums or towering resorts, nor any eateries with Big Macs or Frappacinos on the menu. This is “old Florida.” A place where a bicycle or Island Trolley is the preferred method of transportation and bathing suits are standard attire. Fishermen reel in fresh grouper for the island’s various eco-friendly and sustainable restaurants, local musicians and bands play nightly on historic Bridge Street , and if you come during the Fourth of July, you may even catch Cameron Diaz strolling along the beaches outside of her vacation home.

Oh… and did I mention the sunsets? Pull up a beach chair and prepare to be amazed as the sun and sky put on a beautiful, cotton candy magic show each evening. I’ve traveled to a lot of places and I have to say that Anna Maria Island has some of the best sunsets in the world.

The kind folks at Visit Bradenton ensured my itinerary was packed full of the best activities the island (and area) has to offer. If you missed my Instagram Stories that take you through my entire trip, be sure to watch them in my “Travel” Highlights HERE. I took a short, direct flight on JetBlue from JFK to SRQ and then rented a car to make my way to the island. Total travel time from JFK airport to the resort on Anna Maria Island was about 4 hours.

Ready to trade your sneakers for flip-flops and escape to this charming beach town? Here’s everything you need to know before you hop on your flight:

Where To Stay:

Bungalow Beach Resort

For toes in the sand, “old Florida” romance

Reminiscent of a 1930’s island style resort, this is as close to the water as you can get. There are 16 different bungalows to choose from but the ones with the best views are the Mermaid, Desoto, Hibiscus or Seagull. There’s a small pool on the property, a courtyard with bbq grill and fire pit, and more importantly, several blue and white striped lounge chairs covered by giant umbrellas that offer up a spectacular view of the gulf. It’s the epitome of relaxation. A charming, romantic oasis that will transport you back in time.

Waterline Resort

For upscale amenities and a HUGE suite

If you’re traveling as a group or family or just looking for a little luxury, this is the place for you! Each suite has two bedrooms, living room, balcony and full-size gourmet kitchen (say what!?). Seriously, the suites are bigger than my apartment… and they come with washer and dryers. As one of the island’s newest resorts you can expect incredibly upscale, modern amenities including an awesome restaurant (more on that later), huge pool, marina view, large courtyard where they host events and even yoga classes, and even a shuttle service to take you straight to the beach.

What To Do:

Swing through the trees at TreeUmph Adventure Park

If you’re up for a little road trip off the island, head to TreeUmph for a fun-filled outdoor adventure located on a 14 acre property in Bradenton. You’ll put your fear of heights to the test while zip-lining, climbing, and swinging through 5 unique obstacle courses… all off the ground and in the trees. I got through 3 of the courses but would go back in a heartbeat to try the remaining two!

Wearing: We.Over.Me

Spot dolphins, manatees and wild parrots on an Eco-Kayak Tour

Yes, you can absolutely rent kayaks and explore on your own, but I highly recommend you book a tour through Beach Bums. Our guide, Rick, was so knowledgeable and was able to point out the various wildlife and bird rookeries that I would have missed otherwise. The whole tour lasted about 2 hours so be sure to layer on the sunscreen and wear a hat and sunglasses if it’s sunny out!

Get your zen on with some Beach Yoga

You can do yoga just about anywhere but there’s something about going through Sun Salutation with your toes in the sand that feels so right. If you’re not comfortable doing yoga solo, head to Island Yoga Space for a lovely class in studio, on the beach, or even on a stand up paddleboard. Sadly, the SUP yoga instructor was on vacation during my stay so I’ll have to wait until next time to try it out!

Wearing: Sweaty Betty

Ditch the car and bike around the island

Anna Maria Island is SUPER bike friendly and honestly it’s the most fun way to get around the island. Beach Bums has lots of great beach cruiser options and regular gear bikes if that’s your cup of tea. Each one comes equipped with a cute little basket and parrot “bell.”

Go for a run at Robinson Preserve

Itching to hit some nature trails? Lace up your sneakers and head to this 600 acre coastal preserve located in northwest Bradenton. You’ll find various hiking paths, kayak and canoe waterways, bridges, picnic spots, mangrove forests and a 53-foot-tall tower with a wide-open view of the Tampa Bay area. The tower is my absolute favorite part… the view is truly incredible.

Wearing: Athleta

Where To Eat:

Brunch at Eliza Ann’s Coastal Kitchen

Situated inside Waterline Resort, you’ll find some of the best brunch on the island. I started with a Bloody Mary (garnished with all the fixin’s) and opted for the Shrimp & Grits with a side of seasonal fruit. The portion size was perfect and I’m SO happy that the seasonal fruit consisted of juicy fresh berries and not some sad assortment of unripe melons. Everything was quite tasty, the service was prompt and I left very very happy. Check out their full brunch menu HERE.

Lunch at Poppo’s Taqueria

This little family-owned Mexican inspired restaurant on Pine Avenue offers up delicious tacos, burritos and bowls alongside an awesome selection of craft beer! What I love: it’s vegetarian and vegan friendly, their water comes in award-winning oxo-biodegradable plastic bottles, their Fountainhead, Virgil’s and Jarritos sodas are free of high fructose corn syrup (HFCS) AND there is locally brewed Kombucha. Basically if you’re a wellness junkie, this is the place to be.

Dinner at Gulf Drive Cafe

If you’re in the mood for ocean-front dining complete with a tiki bar, toes-in-the-sand dining, and prime sunset viewing, look no further. This newly renovated restaurant is only minutes away from Bungalow Beach Resort and serves breakfast, lunch and dinner daily. My friend and I split one of their cocktail buckets and I had the Grouper Sandwich, which I highly recommend, especially if it’s your first time visiting the island! View the full menu HERE.

Cocktails at The Doctor’s Office

Okay you guys, this is the coolest cocktail lounge in the whole Bradenton area. As someone who lives in Brooklyn, surrounded by some of the best cocktail lounges in the world, I have to say that The Doctor’s Office gave every single NYC bar a run for it’s money. It’s located in an old doctor’s office (fitting), is super intimate and offers up medical inspired drinks like the “Painkiller” (Aged Rum, Lime, Coconut Cream, Pineapple, and Orange) and “Corpse Reviver” (Gin, Lemon, Kina l’Aero d’Or, Cointreau and Atomized Absinthe). There’s even a cocktail with matcha infused bourbon!! OMG. So good. Check it out HERE.

Treat Yo Self at The Donut Experiment

If you’re craving a sweet breakfast or mid-morning snack, you need to head to this little donut shop on Pine Ave. Fresh, warm donuts pop out of the fryer and onto a drying rack where they are ready to be dressed up in whatever concoction you can dream of! These cake donuts are the perfect size and literally melt in your mouth. I challenge you to eat just one… it’s impossible.