Wine bar$$$$old-townMon-Sat seatings at 17:00, 19:00 and 21:00; closed Sunday
Little Pearl calls itself a neighbourhood restaurant and wine bar, matching a Key West seafood tasting menu to a cellar strong in halves and sake.
Wine focus: Deep cellar of sparkling, sake and half bottles beside a tasting menu
Food: Four-course local seafood tasting menu
Tip: Seatings run at 17:00, 19:00 and 21:00 six days a week; the wine pairing leans on the half-bottle cellar and is worth it.
Wine bar$$duval-streetDaily 12:00-00:00
Grand Vin pours wines by the glass on the porch of an upper Duval conch house, Key West's long-running bottle shop and wine bar rolled into one room.
Wine focus: Old and New World bottles by the glass on a Duval porch
Food: Cheese plates and charcuterie
Tip: Take the porch rail seats for sunset people-watching; the retail shelves mean you can carry the bottle you liked home.
Wine bar$$duval-streetMon 16:00-22:00; Tue-Sat 13:00-00:00; Sun 13:00-23:00
Vinos on Duval pairs a world-spanning wine list with big charcuterie boards mid-Duval in Key West, a calm porch between the street's louder bars.
Wine focus: World-spanning list with homemade sangria and spritzers
Food: Cheese boards, charcuterie and light fare
Tip: The homemade sangria changes daily and the boards are enormous; it is pet-friendly and takes no reservations.
Wine bar$$historic-seaportDaily 07:00-22:00
Funky Rooster turns from Caroline Street coffee house to Key West wine bar by evening, pouring a curated list under local art and rooster kitsch.
Wine focus: Curated bottles across budgets after the espresso machine rests
Food: Bagels and pastries by day, small bites by night
Tip: It is the rare Key West room that works for a laptop morning and a wine evening in the same day.