Welcome to Anna Maria Island!

With temperature of 84 /26 degrees and 361 days of sunshine per year, you’d be forgiven for thinking such as place doesn’t exist.  But it does. With a rustic charm, a laid-back Floridian style and unhurried tropical living, your worries will be far away.  The locals want to get to know you and local businesses welcome you with signs that say ‘come as you are’ promising to ‘feed your soul’; a truly indicative symbol of the wonderful culture that is Anna Maria Island.

City Pier, Anna Maria Island

Anna Maria Island is part of Florida’s Gulf Islands, which includes Longboat Key, Bradenton and Longboat Ranch. Tucked away on Florida’s Gulf coast in Manatee County and nestled between Tampa and Sarasota, the Gulf Islands is only 2 hours’ drive from Orlando, and can be a perfect way to spend a few extra days winding down from a busy theme-park filled adventure at any of Florida’s famous Universal or Disney parks.

The Island consists of three town communities. Anna Maria City is at the north end of the island, where most of the Pinapplefish vacation rentals can be found, amongst some of the largest residential homes on the island.  Holmes beach is in the centre and Bradenton Beach in the south, with its fun shops and restaurants.  However with only 8000 inhabitants on the Island, it is far from being crowded.

Most people visit Anna Maria for the exquisite beaches.  You can relax in the serenity that is Holmes Beach, relax on Tampa Bay beach alongside City Pier, and capture the feel of old Florida on the remote stretch of Anna Maria Beach.  Or simply enjoy the warm seas of the Gulf and the amenities – playgrounds, picnic tables and showers – that the more popular beaches (Manatee, Holmes Beach, Coquina) have to offer.  All of the Pineapplefish houses are no more than a 5 minute walk to one of the island’s beaches. Holmes Beach Anna Maria Island

Wherever you decide to laze, the beaches are true paradise and deliver the most magnificent sunsets to rival anywhere in the world.  Don’t forget to look for the famous Green Flash, a flash that appears just above the crest of the sun, as it is about to disappear.  It only lasts for a few seconds and requires very pure atmosphere with abnormal atmospheric refraction including mirage effects, to be able to create this green flash, so you are very lucky indeed if you experience the green flash.

River and sea fishing are also a popular pastime.  There is nothing quite like casting a line from either City Pier or the Rod and Reel Pier, both historic landmarks on the island, where the scene is set to watch the manatees and dolphins meander past, or to fish at dusk, when the island proudly displays its magnificent sunsets.

No Anna Maria Island vacation is complete without a wander along one or both of the two piers that meander into the delicious waters of the Gulf; The Rod & Reel Pier and the Anna Maria City Pier. Each of these is home to infamous restaurants; Rod & Reel and City Pier Restaurant where you can enjoy a cold beer and sample the delights of the catch of the day or even catch your own.  You may even be lucky and be able to see a shuttle launch some 150 miles away at Kennedy Space Centre when you are here!

The best way to explore Anna Maria Island is by bike.  With delightful narrow winding roads, you can catch glimpses of the numerous species of wildlife on the island, meander down the network of canals on the bay side, and sample some of the delightful cafes and bars along the way.

Family on bikes

Cycling for children is really safe; cars can only travel at up to 25 mph on the island, and will always give way for people on bikes. Our friends, Diane and Lauren at Beach Bums, can cater for all your biking needs and even get them delivered to and collected from your rental home while you’re here.  Beach Bums also have a great selection of golf carts, including a stretched cart, to fit up to 10 people, which is another great and fun way to get around. There is also a free trolley service, which travels daily from Anna Maria Pier in the north to Coquina Beach on the south.

There are so many things to do on Anna Maria Island, as well as fantastic restaurants and great places to eat and fabulous shops, but whatever you choose; you will only want to do it at a slow pace.  Winding down on this island is instant, as you settle in to a taste of Florida’s very own yesteryear paradise.


The Waterfront Restaurant, Anna Maria Island. Steak and GritsThere are so many fantastic Anna Maria restaurants, with every type of food and atmosphere you could possibly want, for anything from an intimate romantic meal, a  family lunch, to a celebration: fine dining with exquisite wines in settings offering breathtaking views, to relaxed surf style, with real southern style boiled peanuts and deliciously thirst quenching cold beer!

Some of our own favorites include The Waterfront Restaurant, which is literally a stones throw from Tampa Bay beach, where you can look out to the City Pier while you dine.  Their crab cakes and fish tacos are amazing. And they have a great and popular bar, serving the best cocktails on the island!

For live music, head to Harry’s! Enjoy a really good night of entertainment, alongside great beer, and good food, including burgers and salads.

The Sandbar Restaurant Anna MariaThere is also the Beach Bistro in Holmes Beach, where you can either dine in the restaurant looking out across the Gulf, or, as we prefer to do, sitting at the bar.  Here, the fabulous bartender will help you choose the perfect wine to accompany a fantastic menu of food and it’s a great way to chat to other diners; a really wonderful and social evening.  And we really love the valet parking – even for bicycles, which is how we always travel up there.

And no trip to Anna Maria would be complete without a visit to the Sandbar Restaurant where you literally can kick off your sandals, and dig your feet into the sand while you eat, and watch the sunset over the Gulf.

There are also lots of other great places to eat, be it light lunches and snacks, including deli sandwiches and salads from the General Store to take the beach, to evening meals: either eat in, or get a take out to enjoy at your rental. From taco’s and a beer from Poppo’s, to pizza or pasta from the Italian Kitchen on Pine Avenue, to treats such as ice cream stores and a donut shop, where you can make your own selection from an array of toppings!

It’s always good to remember, that in the height of the season, these places can get pretty busy, so it’s not a bad idea to book up.


You will not find any major chain store on Anna Maria, that is part of the beauty and charm of our island. But you will find some great places to shop; a mix of wonderful, individual and unique stores.  Pine Avenue, is the main commercial road on the island, where you will find an array of fantastic shops and boutiques, in beautiful settings.

boutique-shopping-on-pine-avenue-5Pine Avenue is also where you will find the Historic Green Village, our sustainable retail park, which is home to the Libby’s Island Jewelry, Joyce Lazzari Gallery, Hometown Desserts and the General Store. The General Store is run by a great friend of ours: Brian, and is open pretty much every day of the year, dawn till dusk, and has everything you need to stock up your vacation rental.  Delicious deli-foods, fresh breads, breakfast cereals, coffees, tea, juices, milk and all cupboard items. There is also a great selection of local craft beers and wines, as well as the largest cooler cabinets for all soft drinks anywhere on the island.

One of the great things about the General Store, is that you are able to order online, so it’s ready and waiting for you to collect when you get to the island, or Brian can deliver it straight to your rental so it’s at your home for when you arrive!  A really great service if you are going to be getting here late at night! Whilst you are at the Historic Green Village, we really hope you take some time to look around the site, and take the self guided tour, where we showcase the technologies that we have brought to the site, share the history behind some of the beautiful buildings that we have renovated, and pop into the General Store to check out some of the charts and tools, measuring the energy input and output on a real time basis.


Anna Maria Island, is rich with history and many landmarks and buildings can still be found on the island today. George Emerson Bean was the first permanent resident on Anna Maria Island, in 1892, settling with his family at the North end of the Island. George and his son George ‘Will’ Wilhelm, are the persons most responsible for developing much of what is now the City of Anna Maria.

City Jail Anna Maria Island In the early 1900’s, Will formed the Anna Maria Beach Company alongside Charles Roser, who made his money selling the ‘Fig Newton’ recipe to the company that became Nabisco.  And, together, they developed Anna Maria Island to become the finest resort on the west coast of Florida, responsible for building a dock at the end of Pine Avenue and a bathing pavilion where the Sandbar restaurant sits today as well as many other historic landmarks, which can still be found.

The Anna Maria Historical Society can be found on Pine Avenue. As well as a traditional home on site and what was the City Jail, they also have some fantastic presentations and displays of many artifacts and photography that represent our heritage. You must take a visit when you are on the island!