You might be wondering, what makes an American restaurant in Key West truly great? The simple answer is: it captures the island’s spirit. As one of Florida’s most iconic destinations, Key West has welcomed generations of visitors and residents, many arriving via the Overseas Highway that connects these sun-drenched islands. And despite being a compact paradise dotted with historic homes and bustling docks, you can find spectacular American classics in just about every corner.
Red Shoe Island Bistro
$$$ | (305) 509-7271 | WEBSITE
For those inevitable moments when you wish you were in Key West, there’s Red Shoe Island Bistro, a cozy restaurant in the heart of the island. The bistro’s welcoming atmosphere and attention to detail make it a standout, so you can savor your yellowtail snapper and a beautiful lavender cheesecake to remember, if need be. Starters like deviled eggs and shrimp toast go quickly, but you can get the Catch of the Day with Key West pink shrimp and tomatoes burrata any day of the week.
Don’t skip the beef stroganoff, which is rich and comforting, or the lobster profiteroles, which will make you feel indulged again. We suggest trying both the award-winning Key Lime pie and the lavender cheesecake, which are equally unique and delicious.
The V
$ | (305) 294-9968 | WEBSITE
The V is known for three things: generous portions of classic American comfort food, reasonable prices that won’t break the bank, and a welcoming atmosphere that feels like coming home. The V is mostly a cozy dining room with a few nautical touches hinting at its Key West location. Yet despite the unassuming, neighborhood exterior, the dishes are pretty exceptional: think perfectly grilled fish with lemon butter or crispy fried chicken with house-made gravy.
There are also wonderfully simple staples, like the mashed potatoes, which are just creamy Yukon Golds with a hint of garlic and butter. You should embrace the warmth, and the friendly, laid-back vibe—and also make sure to order the fish.
Nine One Five
$$$ | (305) 296-0669 | WEBSITE
Nine One Five, a polished American restaurant, operates like a beloved chef’s refined dining room. Guests settle in and linger, sharing stories and special moments, while savoring bacon-wrapped dates from the appetizer menu or enjoying the Toasted almond SemiFredo with dark rum. The elegant space feels comfortably established from years of serving made-to-order Cedar Plank Salmon, Seared Ahi with garden ravioli, and Soul Mama soup to stay.
Head to Nine One Five for a leisurely, memorable, and satisfying dinner for around $75 per person, and try the Waygu burger before finishing.
Garbo’s Grill @ Hanks!
$ | (305) 304-3004 | WEBSITE
There’s no reservation list or fancy dress code at this Key West spot, which is actually more of a taco-shack-beach-hangout. But Garbo’s Grill @ Hanks! also serves fresh, gourmet tacos—an essential item, since the atmosphere is laid-back and kid-friendly. We especially like the Korean BBQ beef tacos here, which arrive bursting with flavor and a modern twist on traditional Korean tastes. Snag a picnic table, order a taco or two, and soak up some island vibes.
Or bring the whole family for a lobster roll, though be prepared for it to be a bit pricey.
Salty Frog’s Bar & Grill
$ | (305) 741-7809 | WEBSITE
Named for a local legend, Salty Frog’s Bar & Grill serves up classic Key West fare like tacos, seafood, and a sandwich that captures the essence of island living, the grouper sandwich. The lively, no-fuss spot piles what seems like a generous portion of fresh, flaky grouper onto a toasted bun along with crisp lettuce and a tangy remoulade, all of which should then be paired with a cold beer from their solid selection.
If you don’t have napkins at the ready, make sure someone close by can pass some over when the conch fritters arrive piping hot.
Mary Ellen’s Bar & Restaurant
$ | (305) 294-7750 | WEBSITE
Watching a server skillfully balance a tray of frozen Irish coffees is a thing of beauty. Which is to say, the folks running Mary Ellen’s Bar & Kitchen in Key West really know what they’re doing. Served with crispy edges and melty cheese, the fried bologna sandwich gets seared again alongside tangy buttermilk ranch. The bologna is juicy, with pockets of sweet, caramelized fat. Each bite tastes better than the last, so much so you almost forget about sprinkling on any spicy homemade buffalo sauce.
Luckily, Mary Ellen’s is open with quick service and a fun, laid-back vibe—sometimes hosting fundraising events on the weekends.
Duffy’s Steak & Lobster House
$$ | (305) 296-4900 | WEBSITE
Classic American steakhouses with a laid-back island vibe are surprisingly scarce in Key West these days, which is why Duffy’s Steak & Lobster House feels like a true find. Not only can you savor perfectly seasoned prime rib or a New York strip steak cooked just right, but you can also enjoy fresh lobster, crab, or teriyaki rib eye alongside local fish and Maine lobster. The atmosphere is less formal restaurant, and more like a cozy, clean spot attached to a relaxed Key West hangout.
In other words, everyone working there feels like friendly, attentive hosts, even if it’s your first visit. Duffy’s offers good value with excellent food and a welcoming environment, so go with your favorite travel companions or take home some of their famous key lime pie—often called the best in town.
Caroline’s Cafe
$$ | (305) 294-7511 | WEBSITE
There are plenty of spots to grab a bite in Key West, but Caroline’s Cafe, which has been a local favorite for years, is a cornerstone of the dining scene. Since Caroline’s is known for its consistently great service and food, you’ll see servers carrying enormous plates full of crispy fish sandwiches and shrimp po’ boys like they’re the only thing on the menu.
This spot is just a short walk from the waterfront, so expect to see families and tourists on sunny afternoons bonding over pitchers of Island Life Lager. And while you might not be able to hear the music playing over the bustle of the patio, you can still do a good bit of people watching while you cross your fingers and hope the next incoming tray of Key lime pie has your name on it.
Seven Fish
$$$ | (305) 296-2777 | WEBSITE
Tucked away in Key West is Seven Fish, a contemporary seafood restaurant serving a fleet of fresh catches, standout crab cakes, and hearty pasta specials. Whether you enjoy blackened mahi with curry sauce or savoring shrimp scampi at dinner time, Seven Fish can transport you straight to a vibrant coastal kitchen—with lots of focaccia-like bread. Visit for a celebratory meal, a memorable date night, or a solo treat yourself seafood feast.
Milagro Restaurant and Bar
$$$ | (305) 440-3534 | WEBSITE
The dinner and cocktail destination Milagro Restaurant and Bar in the Keys is a celebrated coastal treasure. The standout dishes include the Brisket Enchiladas, Grilled Shrimp and Scallops, Octopus, French Onion Soup, and Petite Fillet, and the Key Lime Pie is a must-try for dessert. The service is table service, and the cocktails are only available in elegant glassware.
Dine among the lively mix of vacationing couples, local regulars, food enthusiasts, and special occasion celebrants for beautifully presented risotto, fresh swordfish, and superbly crafted mocktails. The elegant and trendy restaurant takes reservations, too, but then you would miss all the dynamic atmosphere.
Hurricane Hole
$ | (305) 294-0200 | WEBSITE
The seafood-seeker will quickly find a haven at Hurricane Hole, the waterfront restaurant and hangout on Stock Island. Hurricane Hole is named for its protected location by the water, where the fresh catches get prepared simply and served generously. Each bite bursts with briny, coastal goodness. It’s honestly kind of unfair that more fish tacos don’t magically reappear on the plate. This place is charming yet genuinely relaxed, the kind of spot everyone wishes they had in their backyard.
Boat House Bar & Grill
$$ | (305) 294-9191 | WEBSITE
You might not expect a laid-back spot on the harbor boardwalk with fantastic views of the water to serve some of the most satisfying food you’ll find in Key West, but Boat House Bar & Grill is full of pleasant surprises. Everything at this American spot is value-added: from the lively but comfortable atmosphere with an older crowd, to the popular happy hour with half-price small plates, and the generous-as-hell portions.
Make sure to order the flavorful prime rib sandwich or fish dishes, and, if it’s available, the tender steak kabobs with mushrooms in gravy that will melt away any lingering hunger. So bring a friend, or a date, and be transported to a relaxing time by the harbor.
CD Anchor Food Truck Sigsbee
$ | (305) 834-6125 | WEBSITE
On any given afternoon, CD Anchor Food Truck Sigsbee, a mobile kitchen with a permanent spot, serves up satisfaction to the sun-weary crowds of Key West. Loaded with cheese, veggies, and your choice of toppings, every cheese steak is assembled fresh on the spot. You can also dig into massive anchor fries piled with bacon, crisp salads, juicy cheeseburgers, and foldable NY-style pizza slices.
But be prepared: the wings come out piping hot from the fryer, so just be patient and know your flavor explosion is coming.
Miami Subs
$ | (305) 294-0001 | WEBSITE
Miami Subs serves a lineup of sandwiches, fries, wings, and milkshakes from a family-owned restaurant every single day of the week. The chicken sandwich is juicy, the fries are crispy, and the milkshakes are thick and creamy. All of the sandwiches are made to order—with fresh ingredients, customizable toppings, and (in this economy?) surprisingly good ice cream. Stop by lunchtime or dinnertime—it’s a great option for tired kids and families alike.
