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 Florida Keys books by local authors, the friendly staff can direct you to an entertaining beach read like Randy Wayne White's "Night Moves" or Tim Dorsey's "Atomic Lobster." Brad Bertelli's "Snorkeling the Florida Keys" and Bill Horn's "Seasons on the Flats" are perfect for the on-the-water adventurers. They carry both new and used books, and the children's section is jam packed full of books and games to keep the kids entertained.

Recommended for Islamorada's Best Shopping because: The only bookstore in the Upper Keys has an extensive collection of Florida books and huge children's section.

Claudia's expert tip: Watch their calendar for Meet the Author days with book signings and refreshments.

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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 the Keys for seven years, they wanted an excuse to spend more time here, so they opened a sixth shop in Islamorada. Their store is constructed to act as a walk-in humidor. Spanish cedar lines the walls, ceiling and trim. Smokey green Cuban tiles cover the floor, and the air is carefully monitored. They have over 200 brands of cigars, which are all long-leaf and hand-made from places such as the Dominican Republic, Honduras, Nicaragua, Mexico, Bahamas and Miami. They also carry loose tobacco, imported cigarettes and all things tobacco-related such as pipes, cases, lighters, cutters and ashtrays.

Recommended for Islamorada's Best Shopping because: Cigar aficionados can get their tobacco fix at Cigars in the Keys with over 200 brands to choose from.

Claudia's expert tip: The owners are happy to give you a Cigar 101 lesson to help you match the cigar to your mood.

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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 shop. The owners scour the globe in search of unique artifacts and shells. Coral and shells are brought in from the Philippines, Indonesia, Vietnam, and Fiji including nautilus, queen and king conch and polished abalone. Outside you'll find tropical fountain with a garden and koi pond, which prove the perfect setting for larger items like canons, glass buoys, rusty anchors and crab traps. Sea-inspired home decor includes wood and metal wall sculptures, paintings, decorative dishware, lighted glass buoys, throw pillows and more.

Recommended for Islamorada's Best Shopping because: Opened in 2012, Ocean Gardens has high-end nautical gifts for all occasions, as well as that perfect souvenir you can't live without.

Claudia's expert tip: Bring your wallet. This isn't a roadside stand full of mass-produced tchotchkes.

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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 Denny Wong, Steven Douglas, Galatea, ALOR, William Henry Jewelmer and more. The owner hand-picks a diverse range of watches, classic diamond pieces, nautical jewelry and even collectible designer knives--all in fine quality metals such as gold and platinum with precious stones. They've even collaborated with local painter, Pasta Pantaleo, to create limited edition game-fish inspired pendants in 14K gold, enamel, sapphires and emeralds. After enjoying the local sea life on your vacation, you can take home creative pieces with stingrays, mermaids, sea horses, sharks, dolphins and turtles. For the treasure hunter, they carry authentic historical coin jewelry, pendants, bracelets and rings. The knowledgeable staff can help you find the perfect gem for a man or woman.

Recommended for Islamorada's Best Shopping because: This family-owned jewelry store is known for special pieces from couture designer jewelry lines with sea life and nautical themes.

Claudia's expert tip: Don't miss the Islamorada hook bracelet by Montesino in sterling silver and 14K gold.

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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, instead hand-selecting pieces that are exceptional within each medium. Over the years, she has developed a loyal following by continually updating her store with something new and different each month, offering free gift wrap and paying special attention to what her customers enjoy. Check out their collection of Spiritiles. These glass on copper artworks are handcrafted in Georgia and lined with quotes of wisdom, wit and warm wishes. Peruse the wide selection of handcrafted jewelry and funky gifts like purses made from vintage bathing caps.

Recommended for Islamorada's Best Shopping because: This modern gallery is full of whimsical 3-D handmade crafts from over 200 American and Canadian artists in all mediums.

Claudia's expert tip: Visit during Third Thursday Art Walkabout when the Old Highway between the Green Turtle and Hurricane Memorial is filled with local artists showing their wares.

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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 team, Nadine and Glenn Lahti, as well as 20 other local artists. If you're looking for something that's not imported or mass-produced, this is the spot for you. Most of the works have frames that are hand-made in the Keys from lobster traps fished in the Keys. They can even custom make clever signs for every occasion. Their "Islamorada Fish Stories Told Here," sign is especially apropos. The helpful staff can help pick out the piece that is right for you, and during the week, you are likely to find the owners on site. Pieces range from small to large at very reasonable prices.

Recommended for Islamorada's Best Shopping because: Full of local art in frames hand-made from Keys' lobster traps, this funky gallery and gift shop makes owning tropical art affordable.

Claudia's expert tip: They can print it out one of your vacation photos and frame it within hours for the truly unique keepsake.

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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 different styles to create paintings, sculpture, photography, collage, jewelry, ceramics, home d├ęcor and accessories with prices for the buyer looking for a little art memento to the high end art piece--most pieces with a tropical theme. Just walking along the shaded paths and window shopping can be relaxing, but your sure to find a treasure you want to take home. You're also likely to catch the creative process first-hand. Cindy and Dwayne King work in the studio adjacent to their gallery creating bronze and clay sculptures.

Recommended for Islamorada's Best Shopping because: The 40-foot-long lobster lures visitors off the highway, but the artisan village full of local arts and crafts keeps them there.

Claudia's expert tip: Catch the creative process first-hand, as Cindy and Dwayne King work in the studio adjacent to their gallery creating bronze and clay sculptures.

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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 mix-and-match separates in DD cup and up, as well as plus sizes. The knowledgeable staff is hands-on, helping you find that perfect fit in the dressing room. Owner, Kim Berger, prides herself on hand-selecting high-quality brands that appeal to a wide range of women--old and young--such as Sunsets, Swim Systems, Tara Grinna, Eco Swim, Freya, Fantasie, and Elomi. So many fans look forward to coming back each year on vacay, that Lion's Lair has earned a brisk mail-order business. After seeing the challenges of her large cup size customers, Berger added on lingerie and doubled the size of the store. You'll also find a wide selection of cover-ups, accessories and gifts.

Recommended for Islamorada's Best Shopping because: Filled with swimwear styles for all shapes, this boutique carries mix-and-match separates in DD cup and up, as well as plus sizes.

Claudia's expert tip: Take advantage of the knowledgeable sales staff, who can measure you for the perfect fit.

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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 instructors, recognized the trend in 2007 and opened a core boardsports retail shop in the heart of Islamorada. Islamorada is home to two of the best launch points for kiteboarders--Whale Harbor and Anne's Beach. In addition to all the equipment you would need, they also carry the clothing and accessories in name brands like O'Neill, Volcom, Electric, Rusty, NP and 1080. Paddleboarding, kiteboarding, wakeboarding and skateboarding are their specialties, from lessons and tours to rentals and equipment. Hours may vary in the Fall.

Recommended for Islamorada's Best Shopping because: A core boardsports shop, Otherside carries all the equipment you need for paddleboarding, kiteboarding, wakeboarding and skateboarding.

Claudia's expert tip: To document all your on-the-water adventures, you can buy or rent from their full line of GoPro cameras.

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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 and accessories in name brands like Timberlake, Columbia, Costa Del Mar and Guy Harvey. Even if you're not shopping, the store is worth a visit for the saltwater aquarium filled with indigenous fish and full-size boat parked in the middle of the building. You can actually climb aboard the boat, which is the sister ship to Ernest Hemingway's beloved Pilar. Next door is the popular Islamorada Fish Company, or you can head upstairs to the Zane Grey Lounge. Their patio has a prime view of the sunset, top-shelf martinis and cigars.

Recommended for Islamorada's Best Shopping because: This two-story nirvana for fishermen offers one of the largest selections of saltwater, freshwater and fly fishing gear you'll ever find in one place.

Claudia's expert tip: Climb aboard the sister ship to Hemingway's Pilar, which is beached in the middle of the store.

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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