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Anna Maria Island is having a bit of a moment lately, appearing on all sorts of “Best of” lists in national travel publications. It’s also popping up frequently on television travel and home-buying shows. But it’s not a new find for generations of Florida visitors, who have known about the 7-mile long strip of paradise since the first wooden bridge was built to connect it to the mainland in 1921. It’s true that the region of Florida stretching down to Bradenton from Tampa/St. Petersburg covers a massive land area, with the peninsula occupying more than 2500 square miles and Tampa Bay representing almost another 1000 square miles of water. This means that it can take quite a while to drive from point A to point B, even if you take advantage of one of the breathtakingly long bridges across the bay. But with two major airports and plenty of inexpensive flights available to vacationing travelers, Tampa/St. Pete allows for easy travel to some fabulous island destinations on the eastern coast of the Gulf of Mexico — not the least of which is Anna Maria Island. If you’ve ever considered booking one of those cheap fares and leaving the hustle and bustle of the more urban areas behind, we recommend getting in a little “island time” on Anna Maria Island.

How to Get Around

AMI, as the locals call it, still exhibits plenty of “old Florida” charm. Its reduced speed limit even encourages the use of golf carts and bicycles as the primary methods of transportation. Other options to get around the island include the free trolley service that travels up and down most of the island, with service every 20 minutes. It runs from early morning to late at night. Or, you can call the entertaining Monkey Bus — festive buses decorated in island hues — that picks up passengers and takes them almost anywhere on AMI. The hilarious drivers work for tips, and some buses even feature karaoke. You’re bound to be in a jolly mood when you arrive and it’s time to pay for your ride!

Sunset on Anna Maria Island

The westward-facing beaches on Anna Maria Island offer spectacular sunsets.

Where to Stay

Anna Maria Island is home to three separate cities: Bradenton Beach on the south end of the island, Holmes Beach (the largest town on the island, with about 5000 residents) and the city of Anna Maria, which stretches to the northern tip. The latter features some of the most opulent lodging on the island. An excellent home base, allowing you to easily experience the entire island, is the Waterline Marina Resort and Beach Club. It is a member of Marriott’s Autograph Collection of luxury properties. Located near one of the three major entry points of the island, where Manatee Ave. crosses over from the city of Bradenton, Waterline is in a convenient location to reach all sorts of attractions.

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The truth is, you may have to work a little bit to convince yourself to leave the Waterline property, as it strives to be a self-contained vacation destination. Anna Maria Island tends to resist development, so you won’t see many chain hotels or restaurants — the addition of this Autograph property was kind of a big deal. Waterline is perfectly set up for families or groups, with every room designed as a two-bedroom suite with a full kitchen and separate living areas. Balconies are equipped with comfortable furniture. They feature various views of the pool or marina, where you can watch charter boats or rent personal watercraft to enjoy aquatic recreation on Sarasota Bay. The pool area is also home to a fun little pavilion filled with games, like corn hole and table tennis, offering a great way to keep the kids occupied while mommy and daddy soak up some rays.

With exposure to both the Gulf and Sarasota Bay, Anna Maria Island boasts a wide variety of beaches — including public beaches and access points in front of some of AMI’s private resorts. Waterline has its own beach club, shared with its sister property, and guests can hitch a free ride on a golf cart from the resort. There’s a stretch of sand reserved just for their guests. Beach club staff can also arrange chair and umbrella rentals, and sea kayaks and stand up paddleboards are also available for rental.

Waterline's private beach club

Wide beaches and long stretches of shallow water make Waterline’s private beach club the ultimate swimming hole.

Freshwater and saltwater pools at the Waterline

Freshwater pool or saltwater marina? Take your pick!

Where to Eat

Waterline’s signature restaurant is Eliza Ann’s Coastal Kitchen. In addition to hosting a great happy hour at their convivial bar, and featuring casual coastal cuisine, they can also pack a picnic basket for you to take to the beach club. They’ll even help you stock your room’s kitchen with snacks. Eliza Ann’s is open for breakfast, lunch and dinner, and their emphasis on local seafood ensures fresh and seasonal fare. Get the crab hushpuppies! Parking is free and plentiful at Waterline, so if you drive to Anna Maria Island, you can pretty much abandon your car until it’s time to (regrettably) leave.

Oysters at Eliza Ann's on Anna Maria Island

Baked oysters are just one of the excellent appetizer choices at Eliza Ann’s.

There are plenty of dining and drinking options within a short stroll of the Waterline, and you can easily walk to the beach on the west side of the island in about five minutes. There, you can enjoy the spectacular sunsets over the Gulf. A new addition to the neighborhood is a craft cocktail bar called The Doctor’s Office, where they call their boozy drinks “prescriptions.” Divided into cozy rooms, and featuring a well-stocked back bar of spirits to create classic cocktails and new specialty drinks, you can still tell that the building used to house a medical clinic. Other fun spots near Waterline include Duffy’s Tavern, a casual pub known for its burgers, which has been a local institution for more than 60 years. Like many spots on AMI, Duffy’s is cash only … so bring some folding money or avail yourself of the ATM on site.

The Doctor's Office on Anna Maria Island

The Doctor’s Office reserves the right to limit entry, ensuring individual service to each patron. It’s worth waiting in line for a few minutes for a space to open up.

Mixologists at The Doctor's Office- AMI

The talented mixologists at The Doctor’s Office have all the top-shelf medicines to fill your prescription.

Duffy's hamburger- Anna Maria Island

There’s a good reason why Duffy’s is known as “Hamburger Heaven.”

Hurricane Hank’s is another local favorite, offering elevated bar food, cold beer and cocktails in a beachy ambiance. Nearby is The Freckled Fin, a traditional Irish pub with live music and a menu of tasty food that straddles the line between Irish fare and local seafood; they also pull the finest pint of Guinness on the island. The Sandbar is probably the most iconic restaurant on AMI, set on the beach about two miles north from Waterline. Back when the island was still only accessible by boat, a pavilion sat on the site and served as a gathering point for locals. Through the years, there have been many iterations of bars called The Sandbar there, and the latest has been under current ownership for decades. It attracts residents and tourists alike, who watch sunsets, enjoy Old Florida cuisine and partake of strong drinks. It’s a good place from which to take the Monkey Bus home!

Bradenton Beach, which rests at the southern end of Anna Maria Island, is more densely packed with smaller and less extravagant resorts than Waterline. It’s also home to the vibrant Bridge Street, a strip of fun and funky sports bars and restaurants. They cater to guests looking for a slightly louder good time than those “up island.” Many of the hot spots feature live music, and it should be noted that a few are cash-only. So come prepared to have fun! Additional spots worth checking out include, Island Time Bar & Grille, Bridge St. Bistro, Anna Maria Oyster Bar and the Bridge Tender Inn.

Bridge Tender Inn

This convivial little outdoor annex bar at the Bridge Tender Inn will sell you a drink to take with you on your Sunset Cruise. (It’s not only allowed, it’s encouraged!)

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You shouldn’t leave Anna Maria Island without making at least a quick stop in Cortez, one of the last Old Florida fishing villages. Located just across the bridge on the mainland, the small town still houses commercial fishing fleets and processing facilities and provides seafood for restaurants around the region. Cortez is proud of its fishing heritage and is home to the Florida Maritime Museum. Stop by Star Fish Co. for a bite of the freshest seafood available — right off the boat. The cozy little bar and grille serves its food in cute little boxes, the same used by the commercial shrimp plants to ship their product. (Well, not the same boxes … These clean boxes have never had shrimp in them … Unless you order shrimp.) Order a grouper sandwich or some fish tacos to enjoy on the dock with a cold beer, while you watch excursion boats carry guests on sightseeing tours. It’s a great reason to take a later flight home.

The Village of Cortez sign on Anna Maria Island

The fishing village of Cortez is proud of its Old Florida vibe and history.

Star Fish Co.- AMI

If you want to cook at home, you can buy fresh-from-the-sea fish at the market at Star Fish Co.

Star Fish Co. Bar- Anna Maria Island

The fans keep it cool on Star Fish Co.’s outdoor bar. (The cold beer helps, too.)

Food at Star Fish Co on Anna Maria Island

Instead of the expected seafood basket, Star Fish Co. delivers your meal in a box.

What to Do

For a little bit of exercise, take the trolley to its northern terminus at Pine Avenue in Anna Maria Island. Continuing north on foot, you can take any of the public access points over to the beach. There, you’ll discover a part of the island that many visitors don’t encounter. Since most of the houses at that end of the island are larger rental properties, there is a lighter volume of visitors. This means you can explore Bean Point, with its wide stretches of sand, in relative peace. A neat bit of geological trivia is that the sand at Bean Point is made out of quartz. It’s not only soft to lay on, but it also stays cool even in the heat of summer. Continue around the tip of the island for a sweeping view of the mouth of Tampa Bay and the amazing Sunshine Skyway Bridge. Eventually, you’ll end up at Rod & Reel Pier, a famous fishing dock with a little beer bar. It’s an oasis from some of the more touristy parts of AMI. It’s also a fine spot to rehydrate after your long stroll on the beach, and you can take the trolley home from the nearby Anna Maria Pier. Or, you can walk back down Pine Avenue to visit the charming shops as you work your way back to the stop where you originally exited the trolley. If you need another break before heading back south, stop in the quirky Ginny’s and Jane E’s Cafe and Gift Store for some souvenir shopping or a quick bite.

Ginny and Jane E.'s on Anna Maria Island

Everything at Ginny and Jane E.’s is for sale, even the whimsical decorations hanging from the ceiling.

Anna Maria Island's Rod & Reel Pier

Whether you’re there to fish, eat or drink, Rod & Reel Pier is a fun, casual hang on the northeast corner of AMI.

Bridge Street is also home to Paradise Boat Tours, an Anna Maria Island favorite. The company is known for its personable staff of captains and mates who take guests out on excursions to see dolphins and manatees. Sarasota Bay is one of the only places on earth that host a year-round population of dolphins, so you’re almost certain to spot at least a few during your excursion. The 90-minute cruises leave every two hours, starting at 9 a.m., and can be booked in advance on their website. Paradise Boat Tours’ Sunset Cruise focuses more on the history of the region, and it positions the boat for a spectacular sunset view — as long as Mother Nature cooperates. You’ll also get to see a few more of the region’s islands, including Long Boat Key, Jewfish Key and Sisters Key. Long Boat connects to AMI by a causeway and is populated with many resorts and golf courses, but the other islands are sparsely populated and only accessible by boat. Even though they don’t promise wildlife sightings on the Sunset Cruise, you’ll almost assuredly see some!

Paradise Boat Tours- AMI

Paradise Boat Tours departs conveniently from a pier right next to the Bridge Tender Inn’s bar.

Paradise Boat Tours- Anna Maria Island

This pup is the official first mate, accompanying the captain on every excursion.

From private beach resorts to boat excursions, Anna Maria Island might just be the charming Florida getaway you’ve been waiting for!

For even more ideas on how to spend an entertaining vacation in the Bradenton/Anna Maria Island area, visit www.bradentongulfislands.com.

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