A Saturday and Sunday built around the four things Key West actually does better than anywhere else: the Cuban coffee window, the conch counter, the reef catch and the pie argument, finishing with the Stock Island working waterfront.
Day 1Saturday: coffee window, fish wagon, raw bar, Duval
Morning
Start at Sandy's Cafe on White Street at 08:00, the walk-up window attached to a working laundromat, for a cafe con leche and a Cuban mix eaten standing. Walk over to 5 Brothers Grocery at Southard and Grinnell, open Mon-Sat from 06:30, for a bag of bollos to carry.
Afternoon
Lunch at 13:00 at B.O.'s Fish Wagon, the driftwood shack at Caroline and William, for the fried grouper sandwich with key lime sauce. Then Kermit's Key West Key Lime Shoppe on Elizabeth Street for a frozen chocolate-dipped key lime pie on a stick, eaten on the walk back.
Evening
Conch ceviche and a dozen on the half shell at Half Shell Raw Bar on the Margaret Street docks from 18:00. Afterwards, a cold draft and free popcorn at The Green Parrot at Whitehead and Southard, then Captain Tony's Saloon on Greene Street for the last round under the tree.
Day 2Sunday: Bahama Village breakfast, lobster roll, Stock Island dinner
Morning
Breakfast at Blue Heaven in Bahama Village from 09:00, in the courtyard where the chickens wander between tables, for the pancakes and a slice of the towering-meringue key lime pie. Note the courtyard shuts for several weeks each September.
Afternoon
A con leche at the muralled Cuban Coffee Queen window by the Bight, then a hot buttered lobster roll at Eaton Street Seafood Market at 13:00. Walk down to Mallory Square in the late afternoon for the sunset vendors and the buskers.
Evening
Drive ten minutes out to Stock Island for dinner at Hogfish Bar & Grill on the Safe Harbor docks at 18:30, for the Killer hogfish sandwich beside the working fleet. Back to town for a pina colada at Schooner Wharf Bar on the harbour walk.
A single Wednesday spent on the Cuban half of the island's food: the coffee windows the cigar workers left behind, the grocery counters that still press the mix, the bollo, and a Mallory Square dinner timed to the sunset.
Day 1Wednesday: buchi, bollos, roast pork, sunset
Morning
Sandy's Cafe opens its White Street window at 05:00; be there by 07:00 for a buchi shot and a cafe con leche at the stools facing the street. Walk to 5 Brothers Grocery for a second con leche and a bag of bollos, the black-eyed pea fritters almost nowhere else still makes.
Afternoon
Lunch at El Siboney on Catherine Street from 12:30, the bilingual neighbourhood dining room, for roast pork with black beans, rice and plantains. Afterwards, a coffee at Cuban Coffee Queen Roasters at Key Lime Square, where the beans for the windows are roasted.
Evening
Dinner at El Meson de Pepe beside Mallory Square from 18:00 for ropa vieja and the salsa band, timed so you step out into the Sunset Celebration. Finish on upper Duval at The Rum Bar on the Speakeasy Inn porch, working through a flight from a list in the hundreds.
Three days: Old Town, Stock Island and the reef catch
★ 4.7
3 days
Food-led traveller, three days
Thursday to Saturday across the whole island: the Thursday farmers market at Truman Waterfront, the reef-fish dining rooms, a Stock Island afternoon among the marina kitchens and breweries, and a tasting-menu finish in Old Town.
Day 1Thursday: market day, conch fritters, yellowtail dinner
Morning
Open with a cafe con leche at the Cuban Coffee Queen window by the Bight at 07:30, then a sticky bun and a slice of key lime pie at Old Town Bakery in its conch house at Eaton and Grinnell before the case thins.
Afternoon
The Truman Waterfront Farmers Market runs Thursdays only, 13:00 to 18:00, so build the afternoon around it. Follow with cracked conch and key lime aioli at The Conch Shack's sidewalk window on lower Duval around 16:00.
Evening
Dinner at Seven Fish on Truman Avenue at 19:00, closed Tuesdays, for yellowtail snapper with Thai curry sauce. A nightcap at the Chart Room Bar inside the Pier House at mile zero, walls of stacked memorabilia and complimentary bar snacks.
Day 2Friday: doughnuts, Stock Island marina, Louie's Backyard
Morning
Glazed Donuts on Eaton Street opens Wed-Sun at 07:00 and sells out by lunchtime; go at 08:00 for the key lime doughnut with torched meringue. Chase it with an espresso at Red Buoy Coffee, also Wed-Sun mornings only.
Afternoon
Cross to Stock Island for lunch at Hogfish Bar & Grill from 12:30, then a pint at Cayo Hueso Brewing, open Fridays from 11:30, and a Roostica wood-fired pizza ordered alongside the flight.
Evening
Dinner at Louie's Backyard on Waddell Avenue at 18:30, conch fritters on the Afterdeck above the Atlantic before the dining room upstairs. Finish at The Green Parrot, which pours until 04:00 on Fridays and Saturdays.
Day 3Saturday: Bahama Village, half shell, tasting menu
Morning
Breakfast in the Blue Heaven courtyard from 08:30 in Bahama Village, then walk to Kermit's Key West Key Lime Shoppe on Elizabeth Street at 11:00 to settle your own position in the key lime argument.
Afternoon
Oysters and Key West pink shrimp at Half Shell Raw Bar from 13:00 on the Margaret Street docks. Then a warm face-sized cookie and a square of slab fudge at Mattheessen's on Duval, poured onto its marble slab in the window.
Evening
Book the 19:00 seating at Little Pearl, open Mon-Sat, for the four-course tasting built on the local catch. Afterwards, a zombie with fresh pineapple at Tiki House on lower Duval, open until 02:00.
A Saturday spent settling the island's oldest argument in person. Seven counters, seven different readings of the same three ingredients, from a Stock Island beignet to a torched-meringue slice, finishing with a pie shot on Duval.
Day 1Saturday: beignet, doughnut, bakery slice, two shopfronts, two meringues
Morning
Start on Stock Island at Croissants de France, open daily from 06:30, for a key lime beignet with a cafe au lait. Back in Old Town by 09:00 for a key lime doughnut with torched meringue at Glazed Donuts on Eaton Street, open Wed-Sun and prone to selling out by lunchtime.
Afternoon
A sticky bun and a slice of key lime pie at Old Town Bakery at Eaton and Grinnell around 11:00. Then the two shopfronts that anchor the rivalry: a frozen chocolate-dipped pie on a stick at Kermit's on Elizabeth Street at 13:00, and pie in a cup at Key West Key Lime Pie Co on Greene Street at 14:30.
Evening
Dinner at Blue Heaven in Bahama Village from 18:00 for the towering-meringue version in the courtyard, then walk over to Moondog Cafe for the charred-meringue reading of the same pie. Finish with a key lime pie shot off the shotski at The Smallest Bar on Duval.
A Friday that starts late and ends later: an oyster brunch, the afternoon sets on lower Duval, the two saloons that both claim Hemingway, and the handful of Key West kitchens that are still cooking after midnight.
Day 1Friday: oyster brunch, afternoon sets, contested saloons, midnight kitchens
Morning
A late start. Brunch at Two Friends Patio Restaurant on Front Street from 11:00, Basin Street broiled oysters and a Bloody Mary under the awning, which is the correct preparation for what follows.
Afternoon
Fish tacos and a Hog Snort during the afternoon set at Hog's Breath Saloon near Mallory Square from 15:00. Then the argument: Sloppy Joe's at Duval and Greene, and Captain Tony's on Greene Street, in a building the bar dates to an 1851 icehouse. Both bars claim Hemingway drank there; the operators tell it differently and neither claim is settled.
Evening
Free popcorn and a cold draft at The Green Parrot, which pours until 04:00 on Fridays, then singalong sets at Irish Kevin's on lower Duval. Eat afterwards: Korean BBQ tacos at Garbo's Grill until midnight, a grilled cheese and dipping sauces at Mary Ellen's down Appelrouth Lane until 02:00, or a cheesesteak at Mr Z's, open until 04:00 on Fridays.
Savor the flavors of Key West with a cooking demonstration with dinner meal. Watch as expert chefs bring classic island-inspired dishes to life before your eyes.
Watch the sunset over Key West from the deck of the elegant 105-foot schooner America 2.0 and sit back, relax, and see some of the top sights of the area.
Making a trip of these plans? Where to stay in Key West, what to book ahead, and a car for the day trips. Prices and availability open on each partner's site.
HoliduPlaces to stay in Key West · from USD 370 a nightSee stays
LateRoomsPlaces to stay in Key West · from 117 a nightSee stays
