Natalie's Guide to Exploring Anna Maria Island

Sure, Florida is renowned for its thrill rides and blockbuster attractions. But sometimes, the best adventure is found when life slows down, sunsets linger a little longer, and the sand slips between your toes. And there’s nowhere that captures this as perfectly as Anna Maria Island, with endless beaches stretching for seven miles, quaint small-town charm, and a vibe so relaxed you might never want to leave. 

In January 2025, our Head of Brand Marketing, Natalie Sexton, experienced the charm of the Anna Maria Island area firsthand. Considered one of Florida’s best-kept secrets, Anna Maria Island is a 7-mile-long barrier island off the coast of Bradenton on Florida’s Gulf Coast. Often called one of Florida’s best-kept secrets, this 7-mile-long barrier island sits just off the coast of Bradenton on Florida’s Gulf Coast. The two go hand in hand - Bradenton brings a lively, city feel on the mainland, while Anna Maria Island is all about easy-going beach life.  

During her visit, Natalie fell in love with the dreamy beaches, indulged in world-class dining, and tried out all the best coastal activities. From what to do, where to eat, to the most inviting places to stay, Natalie’s insights will guide you to the very best of the Anna Maria Island area. 
 

Natalie’s Favourite Things to Do 

Life on Anna Maria Island really does revolve around the beach. From dolphin spotting to getting artsy with sand dollars, your days quickly fill with little moments that turn into favourite memories. While the beach is definitely the star of the show, there’s so much more to enjoy just beyond the shoreline. These were some of my highlights: 
Paint a Sand Dollar at Shiny Fish Emporium – I didn’t expect to love this as much as I did, as I thought it would be a kid-only activity. But sitting down to paint a sand dollar (a flattened sea urchin) was so much fun. With a rainbow of paints at your fingertips, it’s a perfect way to get creative and make a souvenir that’s totally unique. 

Dolphin Tour with Paradise Boat Tours – This one was a highlight for sure as I saw so many dolphins, and they came incredibly close to the boat - some were even leaping just feet away from our boat. Paradise Boat Tours even guarantees that 95% of their trips see dolphins, alongside manatees, stingrays, and a variety of seabirds. If you love wildlife, this tour is a must. 

Jet Skiing with Anna Maria Island Dolphin Tours – For anyone who loves a little adrenaline, jet skiing here is the best. It felt like being a kid again. Besides riding wild waves, the best part is that you might even see a sea turtle or a dolphin right up close to you. This is adventure and serene moments all in one. 



Luxury Beach Setup by Beach Suites – The beach is the heart of island life, and Holmes Beach is a must-see. Especially as you can skip hauling all your beach gear down there. Beach Suites will set up everything for you: comfy chairs, umbrellas, towels, paddleball, and even a Bluetooth speaker. It honestly felt so luxurious to arrive at the beach and have everything ready and set up for us. 

Historic Bridge Street – Named after the old wooden bridge built in 1922 connecting the island to Florida’s mainland, this street is full of old-Florida charm. If you’re in the mood for a good mooch, this is the place I’d recommend, as I enjoyed wandering through the quirky little shops and treating myself to some ice cream. If you have extra time, I would definitely recommend stopping at one of the tiki bars for a refreshing beverage or two. 

Pine Avenue – If you want a slice of island life, I’d suggest visiting Pine Avenue. I couldn’t resist the independent bakeries that lured me in with their freshly baked cookies and indulgent cakes. 

Pier 22 & Downtown Bradenton Riverwalk – Just a short 20-minute drive from the island, this is a great little side trip. I suggest having lunch at Pier 22 for views of the palm-fringed Manatee River, then stroll the 1.5-mile Riverwalk. My top tip would be to time it for sunset, and its pure magic before heading back to the beach. 
 

Natalie’s Top Restaurants 

Anna Maria Island might be famous for its sea-to-table seafood, but the dining here can rival any big city.  Fresh and bursting with flavour, this little slice of paradise has a great mix of breakfast, brunch, lunch, and dinner spots that make your taste buds do a happy dance. Here are my top picks - eateries with standout food, stunning views, and a buzzing vibe: 

Creperie – There’s something about starting my morning with a crepe that just hits differently. It’s hard to choose between their sweet and savoury options – both were delicious, but the quiches, omelettes, and pastries deserve just as much praise. Add a strong cup of coffee (I don’t drink it, but I've heard it's good), and you’re set for the day. 



North Shore Café – Another breakfast winner, this laid-back spot offers outdoor seating, which I loved for people-watching. From superfood bowls to classic sandwiches and even a glass of wine if you’re feeling fancy in the morning, it’s the kind of spot where I wanted to stay and hang out, even after I’ve finished my food. 

The Donut Experiment – Build your own doughnut, watch it get glazed and transformed into a sugary masterpiece, and then eat it fresh and warm. I saw both kids and adults enjoying this experience, and the doughnuts taste just as good as they look. 

The Waterfront – This was my favourite lunch spot on the island. The grouper tacos blew me away, but everything from juicy steaks to fresh salads and local seafood is on point. Pair it with breathtaking water views, and you’ve got a meal worth lingering over. 



Beach House – If you want sunset views and toes in the sand dining, this is the place. Located right on Bradenton Beach, it has one of the Gulf Coast’s largest gulf-front decks. It’s a place that captures that holiday feeling: a cocktail in hand, a warm breeze in your hair, the sun dipping into the Gulf. 

Shore LBK – Another beachfront favourite, Shore LBK offers an elevated deck and tables, with every seat offering an ocean view. It won me over because the seafood is fresh, the cocktails are spot-on, and the atmosphere is lively yet relaxed. It’s the kind of place you’ll leave but put it right back on your must-do list. 

Oyster River Rooftop – Just over the bridge in Bradenton, this rooftop restaurant is one of my favourites. The grilled octopus starter is still one of my best dishes ever. Plus, you can’t go wrong with fresh oysters and sweeping views of the Manatee River for a memorable dining experience. 
 

Natalie’s Best Places to Stay 

There’s nothing quite like staying in your own villa on Anna Maria Island. Having space to spread out, a pool to cool off in, and the feeling of living just steps from the beach makes the whole holiday feel extra special. We stayed at Boundless Waves, a 6-bedroom home with a private pool, rooftop deck, and an eight-minute stroll to the beach. I loved the high-end feel and the exclusive amenities of a pool & whirlpool spa, which made it feel like a true getaway while still being comfortable enough to really relax and stretch out. 

If you’re travelling as a smaller group, there are also lovely condos that give you more room than a hotel without feeling too big. And if hotels are more your style, there’s a great mix of options both on the island and just over the bridge in Bradenton. These are my top recommendations on where to stay: 

Anna Maria Island Villas - In my opinion, this is island living at its best. Our Anna Maria Island Villas range from laid-back, budget-friendly homes to stunning multi-bedroom mansions just a few feet from the beach. Villas range from 2 bedrooms all the way up to 9-bedroom homes that sleep up to 23 guests. Every home comes with a private pool, a generous living space, and a fully equipped kitchen, so you can truly settle in and live like a local. 

Anna Maria Island Condos - If you love the idea of extra space but don’t need a full villa, our Anna Maria Island condos are a great middle ground. They offer full kitchens, roomy living areas, and 1- to 3-bedroom layouts that can sleep up to 8 people. You get the comfort of home with the ease of a holiday rental. 

Compass Hotel Anna Maria Sound - This is a fantastic all-rounder if you want a hotel with a little bit of everything. Rooms look out over either the marina or Neal Preserve, and the hotel sits right at the gateway to Anna Maria Island, making it easy to enjoy both the relaxed island vibe and the energy of Bradenton. There’s a complimentary breakfast each morning, an outdoor pool, an on-site bar and waterfront restaurant, and even a little shop for ice cream, snacks, and essentials. 

SpringHill Suites – Downtown Bradenton - A great-value all-suite hotel with plenty of space. You’ll have a kitchenette, a private balcony, free hot breakfast, and free parking. The rooftop pool is a real highlight, along with Oak & Stone, the on-site restaurant and rooftop bar serving pizzas, tapas, craft beer, and cocktails. The location right on the Manatee River makes it even better. 

Mello on the Beach - One of the newest beachfront places on Anna Maria Island, and perfectly positioned right on Manatee Beach. The 1- to 3-bedroom accommodations all have kitchens and private balconies or terraces. There’s an outdoor pool, BBQ grills, a fire pit, and lawn games, but the real star is the beach - just steps from your door. 



Waterline Villas & Marina - A beautiful 5-star option in Holmes Beach, just north of Longboat Key. These condo-style accommodations come with full kitchens and all the comforts of home. The marina-view pool is a lovely place to relax, and there are bike rentals, table tennis, and an on-site restaurant, The Chateau Anna Maria, serving French-inspired dishes for lunch and dinner. 

Palmetto Marriott Resort & Spa - For a more luxurious stay in nearby Bradenton, this 5-star resort has it all. There’s a full spa, seven restaurants (including Oyster River Rooftop), and The Beach Club at Riviera Dunes with pools, sports courts, mini-golf, cabanas, and a waterfront lounging area. The Yard hosts live music and outdoor events, making it a fun and lively place to stay. 
 

Natalie’s Insider Tips 

My biggest tip for Anna Maria Island is to ditch the car and slow right down. With a 35-mph speed limit across most of the island and limited parking, it just makes sense to explore on foot, by bike, or by golf cart instead. 

Bike and golf cart rentals are easy to find at shops all over the island. There’s also the free Anna Maria Island Trolley, which runs every 20 minutes and travels the length of the island along Gulf Drive, from Coquina Beach in the south all the way to the Anna Maria City Pier in the north. If you’re out in the evening or heading somewhere specific, the Monkey Bus is another handy option, with rides starting from just $5 per person. 

Carefree beach days start here. Explore our Anna Maria Island Holidays and find your perfect stay.