Coastal boutique cottage with resort wear displayed outside under bougainvillea

Island Guide

Shopping on the island

Two walkable clusters carry most of the island's retail: Historic Pine Avenue at the north end, and Marina Drive in Holmes Beach. Both are cottages rather than storefronts.

Anna Maria's commercial buildings were mostly restored houses rather than replaced with new construction, which is why the shopping streets still read residential. Expect small rooms, tight edits and owners behind the counter.

Anna Maria

Island Cabana

A Lilly Pulitzer signature store on Historic Pine Avenue, resort prints, accessories and gifts in a restored cottage.

Ginny & Jane E's

Part bakery, part antique emporium, part café, housed in the old island schoolhouse and worth the browse even without an errand.

Shiny Fish Emporium

A tightly edited gift boutique of local and imported finds, the reliable stop for a present you didn't plan to buy.

Holmes Beach

West Coast Surf Shop

Florida's oldest surf shop, trading since the early 1960s. Boards, swimwear and beach gear, plus genuine local knowledge of conditions.

The Pink Pearl Resort Wear

Women's resort clothing and accessories on Marina Drive, curated for island dressing.

Sand Dollar Gift Shop

Candles, jewelry and coastal homewares, a small shop with a large gift-wrap output.

Artists Guild Gallery

A non-profit gallery representing local painters, photographers and craftspeople, with rotating shows through the season.

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