Staycation #3: City of Anna Maria on Anna Maria Island

The dunes at Bean Point, photo Bradenton CVB

ANNA MARIA – I am almost embarrassed to admit that it took several trips to Anna Maria Island before I even discovered the beautiful town of Anna Maria (one of three separate towns on the small island, along with Holmes Beach and Bradenton Beach). As I've mentioned, most of my nine years in Florida were spent on or near Siesta Key, excluding an excruciating two years in North Port that truly tested my sanity.

I had been to Bradenton Beach a few times, but had only ventured north of Manatee Avenue on two occasions; once for a pilgrimage to Duffy's and again for dinner at the Beach Bistro. To be honest, I was unaware there was much of anything north of that. Boy was I wrong.

I really meant it when I said I was vacationing local this year and since moving to Bradenton, I've learned a lot more about the island. So my family and I decided that Anna Maria would play host to our inaugural Florida staycation. When we started telling friends, both my wife and I were shocked at how many local people had never spent time on Anna Maria, beyond parking their car at the beach for an afternoon. What little they did know was often misguided and since taking up temporary residence three weeks ago, I have only more good things to say.

First off, many people are unaware that the beaches sport the same sugar cane sand that Siesta is world renowned for. The only apt word that comes to mind is pristine. They are a little narrower, which I think gives it a cozy feel and for some reason the sunsets feel a bit more, I don't know... intimate.

Anna Maria has done a superb job of protecting its character via strict zoning and as a former Siesta Key resident, this is something I greatly appreciate. If you want commercial go to Siesta, if you want insulated condo communities go to Longboat Key. But if you want the sort of quaint charm that northerners associate with Nantucket, Cape May or Newport – Anna Maria is the only place in Florida where I've found that.

My favorite spot so far is the Rod & Reel Pier, a rustic fish shack that serves up incredible food amid the best water view imaginable. I was expecting to pay a premium in terms of either price or quality, in order to enjoy a meal while hovering over the water at sunset, but a delicious grouper Reuben basket and a cold draft beer came in under ten bucks. You can fish off of the pier without a license by purchasing a $2 pass, or just walk the pier and enjoy the view.

Mystical sunsets at Rod 'n Reel Pier, photo Bradenton CVB

Historic Pine Avenue offers a myriad of sandwich delis, ice cream and coffee shops, and if you loop around to Rotten Ralph's you can get the best bloody Mary in town and a pretty good $9.99 all-you-can-eat fish 'n chips. Just around the corner, you'll find more top-shelf dining at Sign of the Mermaid.

Ginny and Jane E's is an interesting combo of coffee shop and antique trader with killer baguettes and the best bagels in SW Florida. When it comes to fine dining, the Sandbar is king. With its picturesque view, exquisite food and Mallory Square like sunsets, this is the crown jewel of the three Ed Chiles restaurants.

The town goes to great lengths to portray itself as family-friendly and it is. But that doesn't mean there isn't plenty for young people to do, something I've found to be a common misconception. Aside from the cornucopia of dinner options, there is as much nightlife as you'll find in just about any beach town.

There are several spots to hear live music, including my personal favorite, Feeling Swell, a surf-themed bar with great food and authentic island atmosphere. Bortells and Decoy Ducks remind me of the Jersey and Maryland beach bars I grew up with – smoky juke-box joints with cold drafts and good music. You can take the trolley ten minutes down to Bridge Street on Bradenton Beach for even more options.

The historic Anna Maria trolley provides free transportation

The free trolley system makes getting around easy and really adds to the island's charm – its open sides and wooden seats, exactly what you'd expect to find in such a place. Between it and the plethora of reasonable bike rentals, you can certainly get by without using your car.

There's not a bad stretch of beach, but head north to Bean Point if you want to find the best shells. The bay at the north end, between the two piers, provides the best waters for snorkeling. There are several charter fishing services available at the marinas, kayak and jet ski rentals, as well as parasailing for the more adventurous traveler.  

Even with all of the activities, the best part of Anna Maria is its people. The locals have an obvious love and pronounced enthusiasm for their home. Every tourist is treated like a guest of honor and most visitors have been coming every year for decades, so don't be surprised to meet travelers who are more familiar with the area than you are.

The best advantage to living close by is the last minute deals. Many of the rentals have minimum stay requirements, so a hotelier or rental agent knows whether a room or house is going to be sitting empty a few days in advance. If you're a spur of the moment kind of person, you can save big bucks by calling Friday morning for a weekend stay.

We're staying at a Annamaria.com property. This boutique rental service manages luxurious vacation properties with opulent finishings and many of the perks that typical resorts lack. Having the privacy and convenience of a turnkey home is great, especially with kids. You get the enjoyment of a vacation without feeling like you've sacrificed the comforts of home. For my wife and I, our careers are always on the calendar, so having wireless Internet and a private, quiet work space near a pool is a major plus.

The Veraranda by AnnaMaria.com

So, whether it's been a while or you've never been, think about a staycation in Anna Maria. It's five miles off-shore, but truly a world away.

Fun Facts: Charles Roser is often called the father of Anna Maria Island, as he financed nearly all of its early development. Roser made his fortune as the inventor of the Fig Newton cookie. Fig Newtons were originally produced by the Kennedy Biscuit Co., which was later bought by the National Biscuit Company, known today as Nabisco -- the stock of which left Roser a very wealthy man. Both Ponce De Leon and Hernando Cortez were among the famous explorers to have stumbled upon the island's shores. In 1948, the island doubled for Hawaii as the set of the big-budget MGM movie, On an Island With You, starring Esther Williams, Peter Lawford, Ricardo Montalban, Jimmy Durante and Cyd Charisse. Many of the scenes is the 1998 film Palmetto, starring Woody Harrelson, Gina Gershon and Elizabeth Shue were also shot on AMI.