For a town with such a rich literary heritage, it's hard to believe that this is the only remaining bookstore in Key West. Key West Island Books has an extensive collection of local interest books, and the devoted staff can help you find that perfect tome. For the bibliophiles, there's an entire section of novels by and about Ernest Hemingway, as well as a vast selection of works by local authors. Books highlighting Keys' cuisine, history, travel and local wildlife promise something for everyone. Watch their calendar for author readings and book signings. Ask about signed works they may still have in stock from past events.
Recommended for Best Shopping because: Whether you feel like beefing up on your Hemingway or diving into a beach read by a local author, this last-standing bookstore has you covered.
Claudia's expert tip: Try these books set in Key West: Carl Hiaason's wacky novel, Bad Monkey, and Lucy Burdette's Key West food critic mystery, Topped Chef.
Ocean Key Boutique is not your normal hotel gift shop. This elegant boutique offers visitors of all ages a well-rounded selection of clothing perfect for the Key West clime. In fact, shoppers often leave the store wearing their new purchases. One of their main lines, Island Company, labels itself an "escapist brand" with resort wear, cute bikinis, classic swimwear, linen separates, vintage sunglasses and island accessories. The store also stocks Tommy Bahama for men and women--the classic go-to for any tropical wardrobe. For women, the bathing suit section is rounded out with mix-and-match separates by Maaji swimwear. This youthful brand combines an unexpected mixture of prints, textures and cutting-edge silhouettes. They'll also find colorful coverups to match. Men can choose swim trunks and boardshorts from Quicksilver, Tommy Bahama, Island Company and Reyn Spooner.
Recommended for Best Shopping because: This stunning boutique is designed to quickly outfit men, women and children in the perfect vacation wardrobe from head to toe.
Claudia's expert tip: Ocean Key Boutique also carries coastal and whimsical gifts, as well as signature items from Spa Terre.
Aqua Beachwear is part of a small boutique chain that includes over a dozen stores throughout the Florida, Arizona and the U.S. Virgin Islands. If you usually dread swimsuit shopping, their helpful staff can help you find the perfect suit no matter your shape and size. They know their inventory and the styles that work for different body types. The suits come in a variety of different cuts, from one-pieces, monokinis and bikini separates in a myriad of colors and prints. Brands range from affordable to top designers like Gottex, Juicy Couture, DKNY, Ralph Lauren, Betsey Johnson, Miraclesuit and more. Add a matching coverup for a flattering ensemble you'll love. They also carry a selection of boardshorts for men.
Recommended for Best Shopping because: Top-notch customer service, flattering styles and a wide selection of designer brands for women makes Aqua Beachwear your first stop for swimwear.
Claudia's expert tip: Aqua was formerly known as the The Beach House, so don't be confused by the name change.
Packed with everything from collectible pieces like Franz porcelain jewelry to inexpensive souvenirs like butterfly pens, this is a one-stop-shop for anyone who loves nature. They offer a wide array of clothing and accessories featuring flying critters, and educational items range from a scholarly field guide to a children's puzzle. For the serious collector, step into the adjacent Wings of Imagination Butterfly Gallery, which offers original artwork by artist Sam Trophia. The acrylic shadow boxes depict the butterfly's beauty preserved and suspended in art form in a spectrum of colors, shapes and sizes. You can choose the specific butterflies for the display case from their large selection. Don't worry, these aren't the same beauties from the garden.
Recommended for Best Shopping because: Packed with jewelry, children's games and a dazzling of butterfly gear, their gift store is one-stop-shopping nature-lovers for all ages.
Claudia's expert tip: You don't have to go through the exhibit at the Key West Butterfly & Nature Conservatory to explore their gift shop.
Belly up to the hot sauce bar to sample their spicy sauces from around the world. (It's free!) The "tasting staff" entertains and makes helpful suggestions while visitors try everything from jerk sauce to dips and "weapons grade" (the fifth and final step of the Peppers Heat Ratings) hot sauces. Cheese and crackers help return taste buds to normal, and each sample comes with a description of what you're trying. You'll be surprised when you realize you've spent over an hour kicking it with some chili sauce. They carry over 900 products, but don't miss their house brand. Habanero jelly beans anyone?
Recommended for Best Shopping because: Shopping for gifts at Peppers of Key West is literally a heart-warming experience. Don't miss their house brand.
Claudia's expert tip: The owners allow outside beverages in, so feel free to bring your own beer, or even dry chicken wings to experience the full effect.
No visit to Key West would be complete without having a slice of refreshing Key lime pie. While who has the best Key lime pie is a hotly debated topic in the Florida Keys, Kermit's always makes the shortlist. Whether you have a classic slice of the tart confection with a dollop of whipped cream or dipped in Belgian chocolate on a stick, you'll quickly see why Florida named it the official state pie in 2006. Kermit's also makes Key lime fudge, candy, sauces and jams--perfect gifts to take back home.
Recommended for Best Shopping because: Kermit's is the spot for everything Key lime. They even have a tasting station for their sauces and jams.
Claudia's expert tip: Not enough room in your luggage to carry all these Key lime goodies back with you? Don't worry; they ship.
At the eco-chic Green Pineapple boutique, everything has a story. With a focus on what they call mindful consumption, the store is packed with creative up-cycled items. Candles are in old tea cups or vintage cans, and silver spoons have been flattened into pendants. Mason jar wine glasses and canvas bags made from recycled sails. They also showcase one-of-a-kind jewelry from around the globe, hand-made wooden kitchen ware and breezy tropical clothing. Other eclectic offerings focus on Fair Trade, organic and support for artisan women around the world such as stylish handbags made in Marrakech. Also home to the Key West Yoga Sanctuary, the shop is filled with Zen decor, ensuring a relaxing shopping experience. Don't miss the organic cafe, date & thyme, in the back where fresh juices and smoothies provide an energetic boost.
Recommended for Best Shopping because: You'll love their collection of eco-chic fashions with a focus on fair trade, organic fabrics and eclectic up-cycled accessories.
Claudia's expert tip: Talk to the sales staff to find out how they support artisan women around the world with their products.
While you'll pass plenty of places on Duval Street selling "Cuban cigars," there's a reason they use those parentheses. This may soon change, but for now buying or selling Cuban-made cigars is still illegal. Key West has a rich cigar history, but most stogies in the Keys are now made in other parts of Latin America with tobacco grown from Cuban seeds. If you ask the guys at Key West Cigar Club and Smoke Shop for a Cuban, they'll tell you to "start swimming." Then they'll gladly help you find the perfect cigar to match your mood from their large selection of humidors. They also have a wide offering of accessories for the smoking connoisseur. You can sit in the antique barbershop chairs in their front display window or lounge on the big comfy couches inside. You may want to stay a spell even if you don't smoke!
Recommended for Best Shopping because: An homage to the island's cigar history, this real-deal stogie joint has a knowledgeable staff who'll steer you to a smoke you'll love.
Claudia's expert tip: Grab one of the antique barbershop chairs in the front window and watch the people passing by on Duval Street.
Off-the-beaten path in Bahama Village, this charming boutique has an air of vintage romance. The intoxicating scents from their apothecary will draw you in with medicines, lotions, perfumes and soaps. Their approach is old-world, pure and simple like the cult-fave Smith's Rosebud Salve (said to be the best lip balm ever). It's easy to get lost among the elegant displays of European chocolates, letterpress note cards, lavender sachets and crisp linens. Their unique jewelry collection includes Spanish Milagros (protective charms) and hand-crafted brass bangles with a polished patina that develops the more you wear them. For the home, there are items like Bolivian wool throws, Syrian glass carafes and candles from the inspired Parisian team of Astier De Villatte. You can tell that each treasure was chosen with care and has a backstory. The owners are on-hand to share those stories with you.
Recommended for Best Shopping because: This charming boutique will draw you in with its aromatic apothecary, hand-crafted jewelry, home decor and other treasures from around the world.
Claudia's expert tip: Take your time exploring this magical shop. You'll find hidden treasures tucked away like vintage brass ladles and lassi cups.
Your first shopping stop in Key West should be the popular Kino Sandals at the corner of Greene and Fitzpatrick Streets. The place gets packed, so you'll want to get there early. Here you'll find "sandaleros" (old-world sandal makers) hand-crafting a variety of styles using natural leather straps and rubber soles. In 1966, owner Roberto "Kino" Lopez, brought his talent with him when he fled Cuba after Castro's revolution. Three generations later, business is booming. Browse the selections for a style you like, and then ask the ladies behind the counter for your size. The best part is the price. Women's sandals start at $14. When you leave, go ahead and put on your new sandals. Your feet will thank you.
Recommended for Best Shopping because: What better souvenir to take home than a pair of leather sandals handmade right in Key West?
Claudia's expert tip: They don't have half sizes and run a little narrow, so you may need to try on a few pairs for that perfect fit.