Quaint could have Pine Avenue’s picture next to in the dictionary. Located in the city of Anna Maria on Anna Maria Island’s north end, Pine Avenue underwent a transformation starting in 2011. It is now described variously as The Greenest Little Main Street in America – due to it’s green building practices – and Historic Pine Avenue.

Lined with restored historical buildings that house unique businesses, Pine Avenue runs from the Gulf beaches on the west end to the Bay beaches on the east end, where you’ll find the Anna Maria City Pier.

You could easily spend an afternoon strolling along the street in the Florida sunshine. Shop in beachy boutiques, stop for ice cream or a made to order donut, dine in a casual restaurant. Walk along the pier and gaze out at the aqua blue-green water. If you’re lucky you’ll see a fisher reel in a catch.

If all that shopping and eating has you craving some exercise you can rent a bike to work off all those calories. Or maybe you’re so worn out you’ll rent a a golf cart to get back to your rental or hotel!

You won’t be disappointed, Pine Avenue truly is one of the prettiest main streets in a small town.