What cultural etiquette should I know for Key West?
Key West etiquette is relaxed, but a few rules are firm. Leave the wild roosters alone, since the city protects them, tip the usual US amounts including the street performers at Mallory Square, and keep glass off the street. Say Conch as 'konk'. The quiet lanes of Old Town and Bahama Village are neighbourhoods where people live.
The roosters are not a toy. A couple of thousand wild chickens live in Old Town, descended from birds kept for eggs and cockfighting before the sport was banned, and the City of Key West protects them. Don't chase them for a photo, don't pick up a chick on Whitehead Street, and don't toss scraps to the hens that walk across the sandy courtyard at Blue Heaven on Thomas Street. Expect crowing from about 5am, so pack earplugs. The second thing locals notice is how you say Conch: it's 'konk'. A Conch is someone born in the Keys, and a newcomer who has stayed seven years earns the title 'freshwater Conch'. You'll see the Conch Republic flag over half the bars on Duval Street, and it comes from a tongue-in-cheek secession on 23 April 1982, staged to protest a Border Patrol roadblock on US 1, with the island still celebrating it every April.
Drinking rules confuse first-timers more than anything else. Bars on Duval Street like Sloppy Joe's and Irish Kevin's will pour your drink into a plastic go-cup if you ask, and walking the sidewalk with it is tolerated. Glass on the street is not, and police do write citations. Fantasy Fest is the 10-day costume festival that takes over late October, loosening the dress standards on Duval with body paint, though public nudity is still illegal and officers enforce it. If you have children with you, avoid Duval between Front Street and Petronia Street after 9pm during the festival. Old Town side streets like Olivia and Elizabeth are residential, and people are asleep behind the wooden shutters, so keep your voice down on the walk back to your guesthouse and don't sit on porches or lean bikes against picket fences.
At sunset, Mallory Square fills with jugglers, tightrope walkers, and the cat man's performing felines. If you stop to watch a whole act, put a few dollars in the hat, because snapping photos and walking off is the move performers resent most. Off the water, dress is casual almost everywhere, and shorts and sandals work at most restaurants, but put a shirt on before you walk into a shop or a cafe. If you visit the Ernest Hemingway Home on Whitehead Street, look at the six-toed cats but don't pick them up: they are a protected colony that the staff care for.
Cultural norms
Key West runs on a level of informality that surprises even mainland Floridians. Greetings are a nod or a casual "hey" rather than a handshake, and strangers on Duval Street will strike up conversation without introduction. Use first names immediately, including with bartenders, fishing captains, and shop owners. Overdressing draws more attention than underdressing: flip-flops and shorts are standard nearly everywhere, though a few White Street and upper Duval restaurants like Santiago's Bodega expect closed-toe shoes and a collared shirt at dinner. If you visit St. Mary Star of the Sea Basilica, cover your shoulders; board shorts alone will earn a look from the regulars.
Tipping follows mainland American norms: eighteen to twenty percent at restaurants, a dollar or two per drink at bars, and fifteen to twenty percent for boat captains after a snorkeling or fishing charter. Cash tips are preferred on the water since many smaller operations run card payments through delayed systems. Most places accept cards, but the smallest food windows along Caroline Street are cash-only.
The quickest way to mark yourself as oblivious is to touch or stand on coral at Fort Zachary Taylor's reef line: it is both illegal and genuinely destructive. Feeding the roaming chickens, which locals treat as semi-sacred neighborhood fixtures, will also draw sharp correction. Key West's culture is explicitly welcoming of all identities, and any disparaging remark about that openness lands badly and fast.
Greetings
Bartenders, charter captains, and guesthouse owners will be on first names with you within a minute, and a handshake works for introductions. Hugs are for regulars at the Green Parrot, not strangers. Ask a local how many years they've lived here, not whether they're from here, since many residents moved down from somewhere else.
Don't do this
- Chasing, feeding or picking up the wild chickens
- Carrying glass bottles or glasses onto the street
- Walking into a Duval Street bar or shop shirtless or barefoot
- Climbing the Southernmost Point buoy or holding up the photo line
- Picking up the cats at the Ernest Hemingway House
- Saying Conch with a 'ch' sound
- Walking through a Mallory Square performer's circle mid-act
- Putting towels or coolers on the African Cemetery memorial at Higgs Beach
- Riding a bike on the Duval Street sidewalk, or riding at night without a light
Tipping
Tip as you would anywhere in the US: 18 to 20 percent at sit-down restaurants, $1 to $2 a drink at bars, and a few dollars to Mallory Square performers. Check the bill first, as some restaurants add an automatic gratuity for groups of six or more.
Dress code
Shorts and sandals go almost everywhere, including dinner at Louie's Backyard, but bikini tops and wet board shorts belong at Smathers Beach and Fort Zachary Taylor, not at lunch on Duval. Evenings stay warm, at 27.7°C at 7pm on 19 October 2026, so wear linen rather than denim.
Religious norms
Key West is a secular town, but its churches hold regular services. The Basilica of St. Mary Star of the Sea on Truman Avenue holds Mass every day, and if you go, cover your shoulders, take your hat off, and silence your phone. Sister Gabriel's grotto behind the basilica dates from 1922, and locals still pray there before hurricanes, so keep your voice low. St. Paul's Episcopal on Duval welcomes visitors, but stay out of the aisles during services.
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