Key West, FL

At Mallory Square, Key West’s waterfront layers naval, commercial, and public history within the same few blocks. Commodore David Porter established an anti-piracy base there in 1823; after piracy was suppressed, wreckers used the property to store and auction salvaged cargo. The Navy’s foothold expanded because the deep harbor and island position controlled important Gulf and Caribbean routes. During the Civil War, Key West was the lone Southern port outside Confederate control, supporting Union blockade and supply operations. Naval aviation arrived at Trumbo Point in 1917, where seaplanes and blimps searched for German submarines and helped establish the Navy’s airborne anti-submarine role. That presence continues at NAS Key West, whose Boca Chica airfield serves combat-aircraft training.

ATTRTore Sætre / CC BY-SA 4.0

Old Town preserves the domestic side of the island’s working past. Shotgun houses built for cigar workers remain in the historic district even though most factories have disappeared. The surviving houses carry that labor history into residential blocks away from the waterfront. Around Mallory Square, former warehouses and service buildings became cultural venues. The Key West Players converted an 1850 warehouse into the Waterfront Playhouse in 1960, and a restored 1853 building houses the Key West Art Center. The city and Old Island Restoration Foundation began restoring the square in 1961 as a community gathering place. Each evening, the Sunset Celebration fills it with craft vendors, street performers, and food carts, returning regular arts activity to a waterfront once used for naval operations and salvaged cargo.

ATTRLarry D. Moore / CC BY 4.0

The surrounding water is both workplace and protected ecosystem. Florida Keys National Marine Sanctuary was designated in 1990 and now covers 4,539 square miles around the island chain. It contains North America’s only coral barrier reef, seagrass beds, mangrove islands, over 6,000 marine species, and protected shipwrecks and archaeological resources. Its shoreward boundary begins at the mean high-water mark, placing local marine activity inside the sanctuary as soon as it leaves land. Commercial and recreational fishing, boating, diving, wildlife viewing, and tourism depend on those waters, making reef condition an economic concern as well as an ecological one. Restoration remains a long-term project: Mission: Iconic Reefs is working toward self-sustaining coral at seven important reef sites by 2040 through outplanting and the reintroduction of grazing crabs and urchins.

ATTRJack Cui / CC BY-SA 4.0

Bus service changed in late 2025 when Key West Rides replaced the fixed North and South lines. The app-based system matches riders traveling in similar directions and provides shared, stop-to-stop trips across Key West and Stock Island, with connections to the Lower Keys Shuttle. That connection preserves a scheduled regional link beyond the on-demand service area. Trips can be requested immediately or reserved later in 15-minute increments. In 2026, service ran from 6 a.m. to 8 p.m. every day except Thanksgiving, Christmas, and New Year’s Day. At day’s end, Mallory Square brings several of Key West’s layers back together: performers and crafts occupy the same waterfront where the Navy began anti-piracy operations and wreckers once sorted salvaged cargo.