You’ll find both unique gifts and schlocky souvenirs in Key West, from coconut postcards and Key lime pies to more crude, lewd clothing and tchotchkes. On Duval Street, T-shirt shops outnumber almost any other business. If you must get a wearable memento, be careful of unscrupulous salespeople. Despite efforts to curtail the practice, many shops have been known to rip off unwitting shoppers. It pays to check the prices and the exchange rate before signing any sales slips. You are entitled to a written estimate of any T-shirt work before you pay for it.

At Mallory Square, you’ll find the Clinton Square Market, an overly air-conditioned mall of kiosks and stalls housed in an old US Navy customs building and designed for the many cruise ship passengers who never venture beyond this supercommercial zone. Beyond the high-priced hat and shoe shops, the real reason to head here is for its free and clean restroom.

Once the main industry of Key West, cigar making is enjoying renewed success at the handful of factories that survived the slow years. Though you will no longer find viejitos (little old men) rolling fat stogies in the streets just as they used to do in their homeland across the Florida Straits, the Original Key West Cigar Factory, 1075 Duval St. (tel. 305/998-9141) has an excellent selection of imported and locally rolled smokes. Also consider booking the 10:30 am or 1:30pm tour at Rodriguez Cigar Factory, 113 Fitzpatrick St. (tel. 305/296-0167), where you’ll learn about the family’s history in Key West as cigar makers dating back to 1831, and watch them prepare, wrap, construct, and roll. Cost is $35 for the 90 minute tour which includes a cigar and Cuban espresso.

Remember, buying or selling Cuban-made cigars is illegal. Shops advertising “Cuban cigars” are usually referring to domestic cigars made from tobacco grown from seeds that were brought from Cuba decades ago. To be fair, though, many premium cigars today are grown from Cuban seed tobacco but in Latin America and other areas of the Caribbean.

If you’re looking for local or Caribbean art, you’ll find nearly a dozen galleries and shops on Duval Street between Catherine and Fleming streets. There are also some excellent shops on the side streets. One worth seeking out is the Haitian Art Co., 1100 Truman Ave. (tel. 305/296-8932), where you can browse through room upon room of original paintings from well-known and obscure Haitian artists, in a range of prices from a few dollars to a few thousand.

Literature and music buffs will appreciate the many bookshops and record stores on the island. Key West Island Bookstore, 513 Fleming St. (tel. 305/294-2904), carries new, used, and rare books, and specializes in fiction by residents of the Keys, including Ernest Hemingway, Tennessee Williams, Shel Silverstein, Ann Beattie, Richard Wilbur, and John Hersey. The bookstore is 10am to 8pm Monday through Saturday and noon to 6pm on Sunday.

For a glimpse of a literary legend or two, check out the small, but cozy and comprehensive Books & Books @ The Studios, 533 Eaton St., (tel. 305/320-0208), a branch of Miami’s lauded, beloved indie bookstore  that was co-founded by a local whose name you may recognize: Judy Blume. She’s often working behind the counter here.


Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.