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...  Read More

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...  Read More



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...  Read More



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...  Read More



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...  Read More



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...  Read More

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...  Read More



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...  Read More



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,...  Read More



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...  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