The Roost is a cocktail bar restaurant in Old Town, Key West.
Editorially verified August 21, 2026 by Lewis Vaughan, TableJourney editor. Source.
Why locals love it: Half a block off Duval behind a liquor-store front, it pours caviar-service cocktails for locals while the crowds walk past.
Tip: Happy hour runs 12:00 to 18:00 and the caviar-and-cosmopolitan order is the move; bottles to go from the shop shelves.
Address: 508 Fleming St, Key West, FL 33040
The Chart Room hides inside the Pier House Resort at mile zero of Duval, the wood-panelled Key West bar once frequented by Jimmy Buffett and Mel Fisher.
Why locals love it: A dozen seats buried inside the Pier House Resort, unmarked from the street and easy to miss even when you are looking for it.
Tip: The keywesttourist guide notes Buffett and treasure hunter Mel Fisher drank here; the room seats barely a dozen, so go at 17:00 sharp.
Baby's Coffee has roasted 100% Arabica beans since 1991 and works from mile marker 15, the road-trip espresso stop on a Key West run up the Overseas Highway.
Why locals love it: It sits at mile marker 15 on the Overseas Highway, so only drivers and cyclists heading up the Keys ever find the roastery.
Tip: Look for the painted eye on the building at mile marker 15, about 20 minutes from Old Town; parking is easy.
Mam's Best Food is the Florida Keys' one kosher kitchen, an Israeli tented counter on Petronia Street under Florida Keys Kosher supervision.
Why locals love it: An Israeli grandmother's tented falafel counter on Petronia Street, known mostly to kosher travellers and Bahama Village neighbours.
Tip: It closes for Shabbat every Saturday and queues build in Jewish holiday weeks; the falafel and shawarma are made to order.
Oasis Mediterranean Cuisine hand-folds Turkic manti and khachapuri in a garden room on White Street, Key West's Central Asian outlier worth the detour.
Why locals love it: Hand-folded Uzbek manti and khachapuri on White Street, a Central Asian kitchen no cruise-day itinerary ever reaches.
Tip: The lush back garden is the seat to take; the somsa pastries and baklava travel well for a beach picnic.
Fisherman's Cafe works a small counter by Key West's Historic Seaport, stacking fish sandwiches with papaya and mango slaw for boat crews and walkers.
Why locals love it: A near-signless sidewalk counter on Elizabeth Street that boat crews use while visitors queue at the seaport's bigger decks.
Tip: Seating is a few sidewalk tables on Elizabeth Street; it closes at 17:00, so treat it as a breakfast and lunch stop.
Mo's Restaurant cooks made-from-scratch Haitian Creole food on White Street, the only kitchen of its kind in Key West, with oxtail and goat stew as anchors.
Why locals love it: The island's only Haitian kitchen sits by Bayview Park, a mile from Duval, and most visitors never learn the oxtail exists.
Tip: It sits by Bayview Park away from the Duval crowds and closes Sundays; carryout runs until 21:30 on open days.
