Exploring the North End of Anna Maria Island

Pine Avenue on Anna Maria Island, FL

I have sung the praises of Anna Maria Island ever since a friend recommended it to me a few years ago.

It’s got buttery white sand beaches, clear turquoise water, small beach town charm, great restaurants, ice cream, and some of the most beautiful sunsets I’ve seen. Colorful beach cottages and local restaurants line the streets and parking isn’t impossible, even on a Saturday.

Anna Maria City Pier - Anna Maria, FL

Always wanting to explore the rest of the island but somehow never quite making it out of my beach chair and away from an ice cream cone at Joe’s Eats and Sweets, I wanted to finally explore the rest of what the island has to offer.

Pine Avenue in Anna Maria Island, FL

Opportunity knocked as my grandparents spent the winter in Longboat Key/Anna Maria this year and, seasoned travelers, it wasn’t long before they’d discovered new-to-me restaurants and activities. Luckily, they didn’t mind their granddaughter tagging along for important blog research (disguised as lots of ice cream and eating).

Last weekend I was able to squeeze in one final visit to their rental on Pine Ave in the northern end of the island. It’s always so interesting to experience a place I’ve visited and known through someone else’s eyes, and a good reminder to always push myself out of my comfort zone and explore outside of what I know. There’s always more to know about a place, maybe even new favorites to be discovered.

Anna Maria City Pier - Anna Maria, FL

While my day and a half stay was short, it was also full of new discoveries. Like The Donut Experiment (thanks grandpa) and The Waterfront Restaurant. Or the Anna Maria City Pier on the bay side with water just as turquoise and clear as the gulf side. Sunset mojitos and key lime pie with my toes in the sand (literally) and watching the sunset with my grandparents and John at Sandbar Restaurant were also highlights. And don’t get me started on the cinnamon raisin bread or chocolate chip croissants at the Olive Oil Outpost…

Eat, drink, and watch the sunset on the sand at Sandbar Restaurant in Anna Maria, FL

Pine Avenue is one of the busier streets, but it also felt distinctly more residential. It draws tourists yet manages not to feel overtly touristy. Just walking a few blocks off of Pine reveals a quiet neighborhood with the occasional beach rental property.

Anna Maria Island north end

As much love as I have for the island, negatives have emerged for me, especially in the past year. The feeling of magic has dulled. The island gets very busy in February/March and traffic can be horrible, especially leaving at the end of the day from Coquina or Bradenton Beaches. There’s also some major construction going on in the area I usually park which definitely takes away from the scenery (nothing like loud machinery to disrupt my beach zen).

Tourism has also seemed to rise. In conversing with a local, Ann, who has lived on the island for 30 years, she mentioned that locals were fighting hard against real estate companies getting total hold of the island. It’s sad to know that there’s a struggle for balance here – it’s a beautiful place, one I escape to precisely because it is free of high rises and rows of cheesy t-shirt shops, and it’d hurt to see it turn into primarily a tourist town. I can’t imagine how frustrating that must be for locals.

Pine Ave in Anna Maria Island, FL

Negatives aside, my visit to the north end was just what I needed to reinvigorate my love and excitement for the island. Rental properties and real estate offices are easily found, but the newer homes being built, while large, are still nothing like the huge mansions going up further south on Longboat Key. Small cottages are plentiful and local businesses seem to be thriving.

Unbeatable sunsets in Anna Maria Island, FL

And something tells me the distinct charm of the island is here to stay. Either way, I’m happy to have discovered my new happy place.

5 thoughts on “Exploring the North End of Anna Maria Island”

  1. What a wonderful way for us to remember this lovely place! Just sorry you don’t have a shot of the charming old small cottage we stayed in. It made one realize what old Anna Maria must have been like in the 1930s.

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