Islamorada Shopping: Breeze in the Keys with Mom-and-Pop Boutiques and Galleries

Islamorada’s four main islands in the Florida Keys are home to a bevy of small independent boutiques and galleries strung alongside the Overseas Highway. While the shopping area isn’t really pedestrian friendly like Key West, these charming spots are only a few miles apart--perfect for any shopaholic. Since chain stores weren’t allowed by law until a few years ago, most of these places are owned and operated by longtime residents. This mom-and-pop atmosphere appeals to locals and tourists alike.

Stop at the two-story World Wide Sportsman to buy your fishing gear and apparel or at Otherside Boardsports for on-the-water sporting equipment. Get beach-ready at Lion’s Lair Swimwear and Lingerie, where they can fit all shapes and sizes in the perfect suit. For tropical and funky local art, visit the Rain Barrel Artisan Village and the Lobster Trap Art Gallery. Gallery Morada brings in crafts and jewelry from around the United States. Looking for that special bauble to remember your vacation, check out the upscale nautical-themed jewelry at Blue Marlin Jewelers. Whether you're a novice or a connoisseur, Cigars in the Keys can match your taste with a high-quality stogie. For Florida-based beach reads and a wealth of children’s books head to Hooked on Books.



Got a hankering for some Florida fiction or history? Hooked on Books is the only remaining bookstore in the Upper Keys. This little indie spot carries titles you won't find in the big box stores. With their extensive collection of Florida and...  Read More

Cigars in the Keys
Photo courtesy of Cigars in the Keys


Cigar aficionados in Islamorada can get their tobacco fix at Cigars in the Keys. Owners Danny and Sheryl Kolod have a lifetime of experience with cigars. They bought the first of their five cigar stores in Cleveland, Ohio in 1972. After visiting...  Read More

Ocean Gardens
Photo courtesy of Ocean Gardens


Opened in 2012, Ocean Gardens has high-end gifts for all occasions, as well as that perfect souvenir you can't live without. You can get lost for hours exploring this massive store that's part nautical gallery, part boutique and part antique...  Read More

Blue Marlin Jewelry
Photo courtesy of Blue Marlin Jewelry


This family-owned jewelry store has established a name for themselves with special pieces from couture designer jewelry lines such as Rolex, Hearts on Fire, Denny Wong, Steven Douglas, Galatea, Artful Images and more. The owner hand-picks a...  Read More



Gallery Morada is a colorful wonderland of modern, whimsical 3-D handmade crafts from over 200 American and Canadian artists in clay, glass, wood, metal, fiber, mixed media and paper. Owner Laurie Wickham eschews items that are mass-produced,...  Read More

Lobster Trap Art Gallery
Photo courtesy of Lobster Trap Art Gallery


You can't miss the colorful storefront of this funky gift shop and gallery next to the Sunset Inn. Bright floats, island music and funny hand-painted signs lure you in. The whimsical store is packed full of tropical art from husband-and-wife...  Read More



The 40-foot-long lobster named Betsy lures visitors off the Overseas Highway for photo-ops, but the artisan village keeps them there. Founded more than 30 years ago, the Rain Barrel is chock full of local arts and crafts. The artists work in...  Read More

Lion's Lair Swimwear and Lingerie
Photo courtesy of Lion's Lair Swimwear and Lingerie


Finding a bathing suit that fits can be a challenge no matter what your size, but Lion's Lair Swimwear and Lingerie has come up with a winning solution. This little-boutique-that-could is filled with styles for all shapes, including...  Read More

Otherside Boardsports
Photo courtesy of Otherside Boardsports


The Keys are known for laid-back sports such as scuba diving and snorkeling, but in the past years other sports like kiteboarding, paddle boarding and kayaking have gained popularity. The owners of Otherside Boardsports, who are both kiteboard...  Read More



World Wide Sportsman is a two-story nirvana for fishermen that offers one of the largest selections of saltwater, freshwater and fly fishing gear you'll ever find in one place. Men, women and children will find a wide variety of outdoor apparel...  Read More


Meet Claudia Miller

Claudia Miller has been writing about South Florida for over 17 years--seven from Key Largo. A budding photographer, she can usually be found stalking a sunset. Despite being a tad...  More About Claudia