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.