Seafood$$$$Four-course tasting menuold-townMon-Sat seatings at 17:00, 19:00 and 21:00; closed Sunday
Little Pearl runs a four-course local-seafood tasting menu from a corner cottage on Olivia Street in Key West, with a deep cellar and three set seatings.
Order: The four-course chef's tasting built on the local catch
Tip: Seatings run at 17:00, 19:00 and 21:00 six days a week; the wine pairing leans on the half-bottle cellar and is worth it.
New AmericanChef Travis Lee$$$$old-townBreakfast daily 08:00-11:00; dinner daily 17:30-21:00
Cafe Marquesa is the Marquesa Hotel's 50-seat dining room in Key West, where chef Travis Lee crisps yellowtail snapper and plates oysters nightly.
Order: Crispy yellowtail snapper with shoestring potatoes
Tip: The room seats around fifty and fills with hotel guests first, so reserve ahead for the 19:00 to 20:00 window.
New American$$$$casa-marinaLunch daily 11:30-14:30; dinner daily 17:00-21:00
Louie's Backyard stacks oceanfront decks above the Atlantic at Waddell Avenue in Key West, serving island fare with the Afterdeck bar right on the water.
Order: Conch fritters on the Afterdeck, then the daily catch upstairs
Tip: The Afterdeck pours until late even when the dining room is booked out; Louie's takes its holiday in September.
Seafood$$$$historic-seaportDinner daily 17:30-22:00
A&B Lobster House has served surf and turf above Key West's harbour since 1947, with martinis, yacht views and the Berlin's speakeasy tucked behind it.
Order: Whole Maine lobster with a classic martini
Tip: Ask for a balcony table over the marina; Berlin's cocktail bar behind the building serves the same A&B menu.
New American$$$old-townMon 16:00-21:00; Wed-Thu 16:00-21:00; Fri-Sat 16:00-21:30; Sun 16:00-21:00; closed Tuesday
The Flaming Buoy Filet Co plays retro supper club on Eaton Street in Key West, searing yellowtail snapper with banana salsa under Star Wars memorabilia.
Order: Yellowtail snapper with banana salsa
Tip: Happy hour runs 16:00 to 18:00 and the room is tiny; Tuesday is the dark night, so plan around it.
New American$$$duval-streetDaily 17:00-23:00
Nine One Five serves its fusion tasting plates from an 1850s Victorian porch on upper Duval, one of Key West's most polished dinner-and-wine evenings.
Order: The bacon-wrapped dates and cedar plank salmon
Tip: The house dates to around 1850 and the porch seats go first; the upstairs lounge takes walk-ins with the full menu.