Mallory Square is a large seafront plaza that rests on the northern outskirts of Old Town, at the tip of Duval Street. At the heart of Mallory Square you’ll discover shabby-chic boutiques selling hip, bohemian clothing and souvenirs. Check out the aromatic Cuban-style cigar stores, which present hand-rolled Key West cigars. For a mix of heritage and dark delights, head to Key West’s first legal rum distillery, which provides a history lesson alongside indulgent tastings. As the sun sets, Mallory Square comes alive with street sellers showcasing handmade beach jewelry and artwork.
New Town
The eastern part of Key West is a bit more modern than the west, and here you’ll get a taste of real, everyday living on streets with a neighborly, family-friendly vibe. East of 1st Street and north of Flagler Avenue is known as New Town, and the area is speckled with small and large shopping malls. For a youthful mix of trendy clothing stores and eateries, head to Overseas Market. If you’re after an array of brand names, head to Searstown Shopping Centre. Alternatively, bargain hunters shopping on a budget should head to the oceanfront Key Plaza Shopping Centre.
Eaton Street
When you’re ambling up Duval Street, why not turn onto Eaton Street? While it has long residential stretches, the walk is enjoyable on a sunny day and you'll also come across some hidden gems, from wine shops to Cuban cafes. The standout attraction is Eaton Street Seafood Market. It's certainly no ordinary fishmonger – there's the retro Art Deco exterior for one thing. As you walk in you’re hit by the dazzling array of bright colors, from Key West pink shrimp and fiery red lobsters to white-orange crab claws and exotic yellow-tail snappers. Further along Eaton Street there's also a cute little cinema, if you fancy catching a blockbuster one afternoon.