Old Town Key West: Walking Duval Street & Mallory Square Sunset

Measuring just 2 kilometres (1.25 miles) from north to south, historic Duval Street is nicknamed 'the longest street in the world' because it runs completely across the island from the Gulf of Mexico (at Mallory Square Pier) to the Atlantic Ocean (at South Beach and the Southernmost Point). Surrounded by over 3,000 preserved 19th-century wooden Conch houses along shaded side lanes like Fleming, Eaton, Southard and Caroline Streets, Old Town is ideal for a slow afternoon-to-sunset stroll.

1. Upper Duval (1400 to 600 Blocks: Galleries & Terraces)

Duval Street changes personality completely as you walk from the Atlantic south end (1400 block) to the Gulf north end (0 block). The southern and middle blocks are leafy and relaxed, home to the Butterfly Conservatory, historic churches, art galleries, cigar rollers shaping habano leaves in shop windows, and the 1890 red-brick San Carlos Institute (516 Duval Street, where Cuban independence hero José Martí rallied cigar workers in 1892).

2. Lower Duval & Historic Saloons (500 to 0 Blocks)

As you pass Fleming Street, you reach Key West's historic watering holes: peek inside the open-air arches of Sloppy Joe's Bar (201 Duval Street), walk half a block west to Captain Tony's Saloon (428 Greene Street, the original 1933 location of Sloppy Joe's where Hemingway drank, with a giant tree growing right through the roof and thousands of business cards stapled to the ceiling), visit the tiny open-air Smallest Bar Inn (124 Duval Street), and hear live music at The Green Parrot Bar (operating since 1890 at Southard and Whitehead).

3. The Nightly Mallory Square Sunset Celebration & Historic Seaport

Every evening starting two hours before sunset (a tradition begun by playwright Tennessee Williams and locals in the 1960s who applauded as the sun went down), the waterfront plaza of Mallory Square at the northern foot of Whitehead and Duval Streets transforms into a free open-air street carnival. Watch unicyclists, jugglers and tightrope walkers perform as 19th-century wooden tall ships glide across the orange sun disc. For a quieter sit-down view next door, grab a table on the wooden pier of Sunset Pier at Ocean Key Resort (0 Duval Street) or stroll 5 minutes east along the Key West Historic Seaport Harbor Walk.