Unique Shops Capture the Authentic Island Flavor of Key West

Once you disembark from the cruise ship in Key West, find most likely find yourself in Mallory Square on the lower end of Duval Street. Duval is the main thoroughfare through historic Old Town and is about a mile of bars, restaurants and shops. The first few blocks you might feel overwhelmed with stores selling cheap knickknacks, “Cuban” cigars and $5 t-shirts. Just keep walking, and you’ll quickly find a rich variety of funky shops and boutiques that capture the authentic flavor of the island.

Quality t-shirts (sans vulgar sayings) can be found just six blocks away at the Key West T-Shirt Factory; they silkscreen Keys-y prints from locals artists. For the best selection of cigars, visit the Key West Cigar Club and Smoke Shop where if you ask for a Cuban cigar, they'll jokingly tell you, “start swimming.” Need some new beach wear? Head to Ron Jon Surf Shop, two-stories of bathing suits, cover ups and boardshorts in brand names you’ll recognize. Looking for something a touch more dressy? Check out the travel-friendly resort wear at Local Color and Wanderlust boutiques. Their flowy styles in linen, silk and cotton can take you from pool to party in no time flat. Top off your outfit with a pair of newly minted leather flip-flops from Kino Sandals. When it’s time for the requisite Key lime pie stop, Kermit’s has delicious slices dipped in chocolate plus plenty of Key lime flavored gifts to take back home.


Duval Street

Steps from Mallory Square, this CVS is not your usual drugstore. In fact, it doesn't even have a pharmacy. Instead it's a two-story mecca for travelers who need to grab-and-go just about anything from sunscreen to luggage. Right by the front door you'll find a sampling of travel-sized toiletries, as well as batteries and memory cards for your camera. World jet setters haven't been forgotten with outlet adapters, money belts and neck pouches for important documents. Don't miss their vast selection of flip flops, water shoes and beach accessories at reasonable prices. They do a high-volume, so you may want to take advantage of the self-checkout machines. Note: if you do need a pharmacy, they have one at another CVS several blocks away on Truman Avenue.

Ron Jon Surf Shop
Photo courtesy of Ron Jon Surf Shop

No matter what your water sport--even if it's just sunbathing--Ron Jon Surf Shop has what you need packed in their blue, two-story Conch House style building. Steps away from Mallory Square, their 4,400 square feet store has swimwear and accessories for men and women of all ages. They carry their own signature line, as well as name brands like Hurley, Billabong, Volcom, Roxy and more. Their laid-back but helpful staff is available to help you find the right fit. Post-swim, they've got you covered, literally, with board shorts, tees, tanks and flirty dresses.

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.


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 and incense from the inspired Parisian team of Astier De Villatte. You can tell that each treasure was chosen with care and has a backstory, and the owners are on-hand to share them with you.

Slip into something a little more comfortable at Wanderlust in the historic Bahama Village. This funky boutique has an eclectic mix of Bohemian wear for women and children with an emphasis on fashion in breathable fabrics--perfect for the island lifestyle. The colorful collection of clothing, accessories, art and home decor has been carefully curated by owner, Casey Crockett, who can help you find the perfect vacation wardrobe. For example dresses by Miami designer, Lorie Lester, feature silks, micro modal and organic cottons that bring out a woman's figure, while still keeping a laid-back vibe. The shop also has local designers like Clara Dara, who creates versatile pieces in soft fabrics that can go from the beach to a night on the town. Don't miss the hand-crafted jewelry, which will complete any outfit.

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 a fantastic collection of local interest books, and the devoted staff can help you find whatever you are looking for. If you're feeling inspired after visiting the Hemingway House, they have an entire section of works by and about the author. Enjoy the local cuisine? Take home the My Key West Kitchen cookbook by Norman Van Aken to recreate some of the island's specialties.

Key West T-Shirt Factory
Photo courtesy of T-Shirt Factory Key West

Beware of the buskers standing in front of stores waving $5 t-shirt signs, thumping techno music in the background. At best, you'll end up with a poor quality shirt. At worst, you may get scammed into buying something way more expensive from these fast talkers. Instead, head to the Key West T-Shirt Factory at the Corner of Simonton and Caroline Streets--about six blocks from the cruise docks. An institution since the 80s, this shop hand prints Keys-y designs from local artists (think cats, roosters, sunsets, palms, coconuts, etc.) onto 100% cotton tees, beach cover ups, sweatshirts, tote bags, hats and more. Prices start at about $15, and they even print with environmentally sensitive water based inks. And no, you won't find any vulgar sayings on these classy t-shirts. You'll need to head back towards the thumping music for that.

Nestled in the heart of the historic seaport across from Half Shell Raw Bar, Local Color is the motherload of resortwear. At 3,000 square feet, this store packs in a wide variety of travel-friendly clothing in natural fabrics like cotton, silk and linen--perfect for the warmer climes. The emphasis is on loose, flowy styles that are figure-flattering, and their colorful displays inspire ideas for layering the pieces with chunky necklaces and graceful scarves. Luna Luz, one of their main brands, designs light and airy pieces that could go from a beach wedding to a night on the town. Another line, Hard Tail Forever, offers versatile tanks, tees, hoodies, skirts and pants in sustainable fabrics and rich juicy colors.

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!

Your first shopping stop in Key West should be the popular Kino Sandals at the corner of Greene and Fitzpatrick Streets. It tends to get packed with cruise passengers, 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.


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