A Guide to Anna Maria Island, Florida

This guide to Anna Maria Island, Florida, contains some affiliate links.

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Last Christmas, during that strange hiatus between Christmas and New Year, the BBC aired ‘The Real Marigold on Tour’.

The series was based on the popular film ‘The Best Exotic Marigold Hotel’, that tells the tale of a motley group of retirees living out their golden years in India. Predictably­, heartache, hilarity and stomach upsets ensue.

The BBC, clearly enamoured by this concept, decided to formally adopt it: rounding up an argumentative group of the UK’s most famous retirees and sending them to various locations around the world. After a week of experiencing life as a local, they then had to make the decision whether to retire there, or to return home.

In one particular episode, the four adventurers are told that they are headed to their final destination: Florida. Actress, Miriam Margolyes, immediately declares she’ll ‘hate it’. One time dancer, Wayne Sleep, starts recalling a holiday to Miami in 1982. They head to the airport unsure of what their time in the Sunshine State will hold.

A guide to Anna Maria Island, Florida

A guide to Anna Maria Island, Florida

A week later, and Miriam is eating her words. She and her fellow travellers are filmed driving through the yearlong sunshine in golf buggies, heading to dance classes and strolling down the beach. Rosemary organises a party for her new neighbours, before telling the cameras: ‘I think Florida is rather wonderful’. Later, Miriam is filmed having the time of her life at an aqua aerobics class.

The episode ends with all four agreeing that they could settle here; the laid-back culture and waterside properties tempting them away from the cold of home. Wayne is filmed shedding a tear as he leaves.

I watched this Florida-inspired episode at the start of this year; just a few days before my own inaugural trip there. I’d be heading to one of Florida’s biggest attractions: the incredible world of Universal Studios. Combined with a recent viewing of Magic Mike XXL, an image of Florida was beginning to form in my mind. Somewhere between Miriam Margolyes aquatic star-jumping, and Channing Tatum’s erotic moves on a Tampa dance floor, I’d come to imagine Florida as a place of endless sunshine; septuagenarians driving golf buggies; dazzling theme parks; impeccable retirement villages and wild nights out. I had Florida sussed.

Or so I thought.

Anna Maria Island Florida

It was a bitingly cold February morning in London, when I first met Kelly. We were eating pancakes in a restaurant close to Southwark Bridge, when she began to tell me about the Bradenton area of Florida, within Manatee County. Director of Communications for the area, Kelly explained that the county was perched on the state’s West Coast and was, perhaps unsurprisingly, famed for its local inhabitants – the gentle and lethargic manatee.

Surrounded by the warm waters of the Gulf of Mexico, manatees spend their days drifting up and down the shallow waters of this region, munching on mangrove leaves and green algae.

“Oh, and there’s an island which sits within Manatee County, too’ Kelly said casually, pouring syrup over her pancakes: “I’ve been visiting it all my life: the sunrises and sunsets there still make me cry”. Opening her phone, she showed me a photo – blushing pink and purple skies framing a white sand beach. Silhouetted pelicans glided above the waves; the tips of their wings gilded gold thanks to the setting sun.

It was unbelievably beautiful.

“It’s called Anna Maria Island, Florida”, she said, smiling, “I think you’d like it there”.

A guide to Anna Maria Island, Florida

A guide to Anna Maria Island, Florida

Anna Maria Island – a barrier island just seven miles long and two miles wide. Lapped by the clear waters of the Gulf of Mexico, the Island is home to manatees and dolphins; beautifully maintained cottages and historic, wooden piers. A Florida native like no other, Anna Maria rejects the crowds; priding itself on its ‘old Florida’ feel, largely unchanged since the 1970s.

Here, buildings can rise no higher than two stories, the high street- Pine Avenue – demands strict adherence to eco-friendly rules, and the local café is called ‘Ginny and Jane E’s’. At sunset, holidaying families and locals gather at Bean Point – a dazzlingly, white expanse of beach at the northerly tip of the Island – to watch the sunset. They bring deck chairs and drinks, hold hands or simply watch the changing colours of the horizon alone – arms folded and silent.

Putting down my knife and fork, and pushing my pancakes aside, I wrote down my bucket list destination for 2017: Anna Maria Island, Florida.

A Guide to Anna Maria Island, Florida

Getting There

And so it was that we landed at Tampa airport one late afternoon in early November, promises of spectacular sunsets and old Floridian hospitality tempting us across the Atlantic. We would be staying on the Island for one week, exploring not only its stunning seven miles, but the neighbouring city of Bradenton and the historic village of Cortez. Whilst we flew directly to Tampa, collecting our Hertz hire car there, visitors can also fly to Orlando – the drive onwards a little over two hours.

Arriving as the sun began to slip from the sky, we had a chance to finally catch our breath; the sticky Florida evening creeping through the car windows as we drove south on the I-75. The route from the airport is incredibly straightforward: simply head southward until you reach the iconic Sunshine Skyway Bridge. Having scaled its dizzying heights, you’ll find yourself in Bradenton, where you’ll need to cross just one final bridge before arriving on the Island. In total, the drive took us just under one hour.

Now dark, we crept slowly up the Island’s roads, passing signs for streets named ‘Mangrove Avenue’ and ‘Poinsettia Road’. It was incredibly quiet, the only sound coming from the waves that lapped at the edge of the Island’s slender land. Passing smart, clapboard cottages decorated in dusky pinks, we eventually turned onto our road for the week. Our home – Island Sunrise – appeared through towering palm trees.

A guide to Anna Maria Island, Florida

This enormous, sage green villa came courtesy of Anna Maria Vacations, and was -until very recently – a family home. Proudly dubbed a piece of ‘Old Florida’, the stunning villa featured its own pier (complete with a gaggle of pelicans), wide verandas, swinging chairs and creaking floorboards.

Walking in, living room windows looking out onto sparkling waters, I was already mesmerised. Sepia toned photographs of the Island in its former years filled the walls, and an old 1950s telephone rested in the corner. If the rest of Anna Maria Island was like this eclectic home, then it was going to be a special week.

Things to Do In Anna Maria Island, Florida

After our first night on the Island, we woke up ready to explore. Looking out the window, the scene outside was almost otherworldly; a watercolour painting that blushed and shimmered. The morning sky was illuminated a soft pink, as though someone had dusted it with a rosy blusher, and below, the water lay perfectly still. At the edge of our pier a group of egrets had gathered, eyes fixed on the water for any jumping fish. As we stood there – a little gormlessly in our pyjamas – the hues of the sky gradually changed: a pink to a violent, a deep purple to a bright blue.

A guide to Anna Maria Island, Florida

Eventually tearing ourselves away, we checked our guide to Anna Maria Island, Florida. Today, we’d not be exploring Anna Maria Island, but neighbouring Bradenton – one of Manatee County’s cities. We were intrigued. Why head there when you had this beautiful Island to explore? What could be there worth seeing?

We hurried into our car – Tampa FM playing – and headed back to the mainland.


South Florida Museum and Planetarium

There are so many things to do in Anna Maria Island, Florida – and one of them, surprisingly, is the opportunity to explore space.

Almost nine months since she’d first tempted us with her tales of Anna Maria Island, we were reunited with Kelly, our official tour guide for the week. She explained our first stop would be Bradenton’s South Florida Museum: the largest natural and cultural history museum on Florida’s Gulf Coast. “I used to work here” she said smiling as we pulled up in front of the Museum’s grand entrance, “it’s got a long going on!”

A guide to Anna Maria Island, Florida

She explained that this unique Museum offered 3 for the price of 1 in terms of its attractions: boasting not only exhibitions concerning local history and culture, but the dazzling Bishop Planetarium Theatre and the Parker Manatee Aquarium, home to rehabilitating manatees and local sealife. “For a small city, this museum is a little over the top”, Provost and COO, Jeff Rogers had told us laughing, as we were led to the Planetarium.

Seeped in darkness, we entered the vast dome and sat back in our reclining chairs: an immersive trip into space about to begin. For an hour, we travelled the universe and mused existential questions; Jeff trying to explain Dark Matter as we navigated Black Holes. It wasn’t the introduction to Floridian life I’d expected – no beach walks and no aqua-aerobics. Yet it was brilliant. After stargazing, we ended our tour with an introduction to a group of animals that we couldn’t miss: the Manatees.

Inside a tank holding 60,000 gallons of water lived Baca, Lagoon and Gale. All victims of either cold stress or propeller injuries, the manatees were living here until they were back to full health. I was star struck: mesmerised by these real-life versions of the county’s mascot. Looking like something between a hippo, a seal and a small elephant, these gentle and calm creatures clearly had their own personalities. As Lagoona swam fast laps around her pool, she nipped and nudged at the others, encouraging them to pick up the pace. They would speed up half-heartedly, before slowing down to eat cabbage; a favourite manatee pastime.

On our way out, we headed to the ground floor, now stood underneath the giant aquarium. Here we had a full view of the animals as they swam lazily past: their bellies above our heads. It was a fantastic introduction not only to a surprisingly diverse museum, but to Manatee County itself and from its very own stars of the show.

Village of the Arts

“I’m not sure how to describe this next place”, Kelly said, as we drove to our next stop. The hot Florida sunshine beating down, we began to turn into residential streets. On my left, a deep purple cottage appeared – in its garden a dazzling collection of mirror-covered sculptures. Next to it, a hot pink house proudly stood; a crowd of painted flamingos gathered in the front garden. Nearby, a Frida Kahlo sculpture peeped over the hedge.

Gradually, each vibrant house gave way to the next, until whole streets stood an eclectic paint box of colours. We had arrived in Bradenton’s Village of the Arts; a must-see when considering things to do in Anna Maria Island, Florida.

A guide to Anna Maria Island, Florida

A guide to Anna Maria Island, Florida

A guide to Anna Maria Island, Florida

A live-work community, the Village of the Arts is home to a host of historical cottages, posing as both homes and dazzling galleries. Painted vivid colours and with gardens filled with dedications to the Virgin Mary and Mexico’s Day of the Dead, the neighbourhood is a fantastic place to explore. As we walked through, I spotted a blue cottage offering fish tacos and a green home housing a bakery – guests seated inside the living room. We realised that every inch of this neighbourhood had its own hidden surprise: whether it be a skeleton mural or a yoga studio; a statue of a manatee, or a quilt shop. It was a village truly like no other.

A guide to Anna Maria Island, Florida

A guide to Anna Maria Island, Florida

A guide to Anna Maria Island, Florida

Admittedly, when I’d first conjured up my image of Florida – Miriam Margolyes in a swimsuit still very much front of mind – I’d not imagined that it would include such creativity and originality. This Florida was wildly eclectic, free-spirited and fun. The Village of the Arts was a small corner of Manatee County that may have changed my opinion on Florida, entirely.

Anna Maria Island

Our second day dawned to an equally spectacular sunrise. Claire stood against the window between 6 – 7am, watching as the sky changed. She barely moved for sixty minutes. Today, we would be adjusting to island life with a full day on Anna Maria Island, with the chance to experience a taste of the old Floridian lifestyle.

A guide to Anna Maria Island, Florida

A guide to Anna Maria Island, Florida

For an Island just seven miles long, there is a lot to do in Anna Maria Island, Florida. As we left our house, a small crowd of cyclists passed by; the morning commute in full swing. Yet their bikes were not grey city bikes, but bright purple or mint green – their bells shaped like parrots and their rider’s feet bare. (You can hire these bikes from Beach Bums, on Pine Avenue). Furthermore, people were not heading to the office, but to Pine Avenue for a cinnamon roll from Ginny and Jane E’s, or to the yoga studio for a class.

It was a commute I could get used to.

A guide to Anna Maria Island, Florida

A guide to Anna Maria Island, Florida


It’s rare that island life lends itself to incredible retail experiences. Yet Anna Maria Island begs to differ. On our first morning – the sea mist still rolling in – we headed to Pine Avenue, ‘the greenest little high street’ in America. Here, stores are all independent, including shops such as the Olive Oil Outpost, specialising only in the finest balsamic vinegars, and gift shops overflowing with luxury clothing or toiletries, such as the Pink & Navy Boutique. Each store is housed inside a traditional wooden cottage, some of them transported to the Island by train from Chicago – purchased from the department store Sears and Roebuck. Even the Estate Agents was painted a mint green; Barbie pink lettering decorating its walls.

A guide to Anna Maria Island, Florida

A guide to Anna Maria Island, Florida

After a breakfast of doughnuts at the incredible Doughnut Experiment, we visited what would become our favourite store on the Island: The Shiny Fish Emporium. Walking inside, we were met by a small Shih Tzu: Kiwi. Behind her, her owner (and owner of the store) Rebecca appeared: “Welcome to the Shiny Fish Emporium, ladies” she said. Rebecca personified everything about her store: a beautiful, peaceful, oasis of calm. Looking around – homemade jewellery hanging from pink stands and illustrations dangling by coloured ribbons – I had the immediate feeling I could never leave this place.

A guide to Anna Maria Island, Florida

A guide to Anna Maria Island, Florida

Rebecca and her husband, Chris, were originally from New York, moving to Anna Maria Island to escape the rat race and the cold. Here, they decided to set up a store that let their creativity run wild, offering families a ‘sand dollar’ painting experience.

And so it was that Claire and I found ourselves in painting shirts, focused intently on painting our delicate shells that particular Friday morning. In the background, Christmas music tinkled and Rebecca offered mugs of steaming tea. Chris, an illustrator, was also on hand to help the artistically challenged – i.e. people like myself – skilfully drawing little characters onto the flat shells. It was a lovely morning, in a truly lovely store – and one that represented all that Pine Avenue stood for: creative, independent and welcoming.

I couldn’t write a guide to Anna Maria Island, Florida, and not include this beautiful little spot.

A guide to Anna Maria Island, Florida

A guide to Anna Maria Island, Florida

Yoga & Paddle Boarding

“Listen to the sounds surrounding you and feel the water beneath you”, our yoga instructor, Rachael said gently. Overhead, an osprey called out and the water lapped gently at my board. Our second day had begun with a SUP yoga class, having already paddle boarded from the sleepy mangroves out onto one of the Island’s wide canals. For one year back in 2015, I considered myself a legitimate yogi, attending classes four times a week in a bid to get over a boy. By the end of the year, I was touching my toes.

I was limber.

However, two years later and I’d failed to maintain my regular down-dogging; my hamstrings now screaming as we folded forward into a stretch. Yet despite the pain, I was in heaven.

With the Florida sun on my back and views out over the water, this was one of the most scenic yoga classes I’d attended. Whilst the gentle rocking of the board meant you had to engage your core as you’d never engaged it before, the entire class was an incredibly peaceful experience.

A guide to Anna Maria Island, Florida

Paddling back Rachael explained that she also held classes at Anna Maria’s Island Yoga Space, but that these classes were her favourite. “People always think they’re going to fall in, but it’s much more gentler than that. The water helps you be present and in the moment. It’s very zen”. I couldn’t have agreed more.

Whilst there are lots of things to do in Anna Maria Island, Florida, this is perhaps one activity you must do.

Boat and Canoe Tours

Of course, I couldn’t write a guide to Anna Maria Island, Florida, and not include its stunning marine life. Indeed, visit Anna Maria Island and it’s difficult to not only ignore the water surrounding you, but the wealth of life in it. Dolphins and manatees are lifelong inhabitants of the area: non-migratory dolphins living in the shallow waters surrounding the Island for their entire lives.

Paradise Boat Tours

With thick sea grass and mangroves to hunt and live amongst, it turns out that Anna Maria Island is not only a paradise for its human visitors, but for its underwater inhabitants, too. Our first foray into this underwater world came courtesy of Paradise Boat Tours, as we headed out towards the Tampa Bay to spot dolphins. As our boat bounced over the surf, I imagined that we were far out at sea; a bottomless ocean below me.

We then passed a man stood in the water, the waves barely reaching his knees.

“The perfect environment for the dolphins,” our guide said laughing. After passing the glittering, waterside home of a Cocoa-Cola Executive, our boat came to a standstill. We held our breath. Already, a few dolphins were spotted, their fins rising and falling in the shallows. Turning to look at them, I then heard a rush of water to my left: a male dolphin seemingly suspended in the air next to the boat. People gasped.

For five minutes, this dramatic little dolphin jumped through the air alongside the boat, keen to impress either us, or a local female. Having only met dolphins once during an ill-fated trip to a resort in Jamaica, seeing them in the wild was a wholly different experience.

Eco Kayak Tour

A few days later and we exchanged our paradise boat for a small kayak, courtesy of Beach Bums’ and their Eco Tours. Gliding out onto the water, our guide – Rick – led the way. This tour was gentler than the boat ride, and whilst seeing dolphins was a bonus, it also focused on the smaller inhabitants of Anna Maria. As Rick told us about his childhood on the Island (idyllic, of course), we paddled past a bird rookery, where Roseate Spoonbills, Blue Herons and White Egrets lived.

The Herons reminded me of wizards; long feathers hanging from their beaks like beards. Passing a mangrove island, we arrived on a small spit, where Rick waded around for oysters and giant clams.

As he searched, he told us stories from the Island, including the dramatic Skyway disaster of 1980. On May 9th, a heavy fog and storm settled over the Island. Rick, who normally worked on the mainland, didn’t have to head there that morning or cross the notoriously steep bridge.

Rick clearly had someone watching over him.

At 07.38 a freighter ship ‘Summit Venture’ hit the bridge, the 19,734-ton ship causing the bridge to crumble. As a result, 35 motorists lost their lives. However, one car managed to stop just 14 inches from the gap – a man who would later become famous for returning to his car to collect his golf clubs.

Collecting our kayaks and gliding back, Rick explained that the disaster is one of the worst things to happen on the Island; but one that at least has a punch line. This beautifully peaceful tour was one of the best things we did in Anna Maria Island.

A guide to Anna Maria Island, Florida

A guide to Anna Maria Island, Florida

Horse Riding (and surfing and skiing)

Every now and again, a person will experience an out of body experience – a moment when the reality of that particular moment is magnified. You’ll wonder what on earth you’re doing. How did this happen? How will I even begin to explain this to anyone?

I had such a moment as I clung onto a horse’s tail as it ploughed through choppy waters; the speed of the thing forcing my bikini bottoms around my ankles. Struggling to keep my pants from slipping past my toes, I looked ahead of me – my horse moving like an Olympic swimmer. “Congratulations, you’re horse skiing!” my guide shouted from ahead, as I sped across the water.

“So this is life” I thought as we sped past a boat of onlookers. Next to me, I saw Claire’s face appear from behind her horse, Alabi. The dark hair of her horse’s tail had mixed with her own. She looked like a strange and startled Cruella De Vil.

Located just off Anna Maria, Beach Horses offers visitors the chance to not only horse ride, but to ride the horses as they swim. For thrill seekers – or those simply bored of traditional horse-riding – they also offer the ‘horse skiing’ experience and ‘horse surfing’ activity that I had also tried earlier. This involved standing on the back of the horse as it swam; an activity that required clenched bum cheeks and almost superhuman balance.

It was bizarre, surreal but brilliant fun. As we turned back (and now firmly seated atop my horse), he began to swim powerfully through the water; views of Tampa Bay stretching out ahead of us. It is almost certainly an experience I’ll never forget and absolutely something to include on your list of things to do in Anna Maria Island, Florida.

Beaches & Sunsets

On that cold February morning earlier that year, Kelly had tried to describe the sunsets that grace Anna Maria Island. “I promise you that they are the most beautiful you’ll see anywhere on earth”. I’d nodded politely, humouring her. I’m sure they were beautiful.

A guide to Anna Maria Island, Florida

However, come November and whilst stood on the powder white sand of Bean Point, I realised that Kelly had not been lying. The horizon ahead of me was endless; no start point and no finish line. As the sunset, a wash of pink and purple cascaded across the sky; the white sand bouncing the light upwards. Close to the surf, flocks of egrets took flight – fluttering silhouettes against the setting sun. Somewhere, someone was gently playing acoustic guitar.

It was a sunset that took a breath away and one that I would watch again on my final night, with a lump in my throat.

A guide to Anna Maria Island, Florida

A guide to Anna Maria Island, Florida

If you’re visiting Anna Maria Island – or indeed need a reason to visit – let the sunsets be it. Indeed, they should perhaps be front and centre of any guide to Anna Maria Island, Florida.

The soft, endless beaches of Bean Point, Longboat Key or those that run along Gulf Drive North, are places not only to spend your days, but your evenings; offering the best seats in the house for the sundown spectacular. It’s a moment that the whole Island seems to wait for, a destination defined by its love for the sun’s daily cycle. Each morning, whilst collecting my coffee from a small café next door, I was asked if I’d seen last night’s sunset. “It was beautiful”, the owner would tell me.

I imagine it’s a phrase she says daily.

Final Thoughts

Anna Maria Island, Florida, sets itself apart from the rest of the Sunshine State. It is peaceful, independent, charming and determined to uphold a piece of 1950s Florida. Each evening, locals sit on their verandas; their clapboard cottages painted pastel shades. Families gather on the beach and local restaurants fill with those seeking locally caught seafood. Here, there are no grinding Tampa nightclubs, no identikit retirement villages, and no screaming theme parks. It’s a uniquely peaceful place; an island facing the horizon, waiting for its next sunrise.

I can’t wait to return, ready to join it for its next display.

Listen to our guide to Anna Maria Island, Florida via our podcast here.

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19 comments so far.

19 responses to “A Guide to Anna Maria Island, Florida”

  1. Riya says:

    Awesome tips. Great article, thanks!

  2. Zoe says:

    Beautiful photos 🙂

  3. Unta says:

    Nice eye for details. Place looks amazing, those sunsets are magical.

  4. WOW I love all your photos, they are amazing. Im craving a trip to Florida now

  5. Lindsey says:

    This place is so beautiful! I had no idea it existed! Now I want to go 🙂

  6. Carmelatte says:

    Have just been to FLorida <3 Love the vibe!


  7. Anisa says:

    I haven’t heard of Anna Maria island before but it looks lovely. I especially like your sunset shots!

  8. Kaylie | Happiness Travels Here says:

    This place looks so beautiful, I definitely want to visit next year when we are in the USA.

  9. Dani says:

    You have me convinced! I’ve been to Florida four times and have never heard of this place. Now I want to go there!

  10. I absolutely loved Anna Maria Island. I’m visiting again next weekend and can’t wait!

    Happy Tuesday!

  11. Jo says:

    We are here now and have just spent the morning kayaking with Rick who mentioned he had met you when we said we were English! Your article sums AMI up perfectly, it’s the most beautiful, laid back place I have ever visited. We leave tomorrow and are about to head to Sandbar for a final meal, cocktails and sunset.

    • The Twins says:

      Oh my gosh, Rick! Lovely Rick! Did you enjoy your tour? It’s such a lovely way to see the Island, isn’t it. We are incredibly jealous you’re there but hope you had the most incredible meal at the Sandbar and soaked up that final, perfect sunset! xxx

  12. Anna says:

    This sounds amazing! I’m not a huge fan of Florida but my boyfriend’s parents have a house in Orlando and we are going in three weeks. I’ve been looking for somewhere to take a trip for a couple of days and Anna Maria Island looks perfect – thank you!! xxx

    • The Twins says:

      Hi Anna! AMI will be the perfect escape if you’re looking for something smaller and more authentic. We hope you enjoy it 🙂


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