This Upper Key favorite has been around since 1982, serving fish like Mahi-mahi, yellowtail snapper, and grouper in a myriad of creative ways that include Black and Bleu (topped with blue cheese crumbles and baked, then topped with a cream sauce of bleu cheese, garlic, blackening seasoning, and white wine) and Hemingway (lightly breaded with Italian breadcrumbs and baked, topped with white wine, garlic, basil cream sauce). Other popular items include fried cracked conch, and coconut shrimp served with poppyseed mango dressing.

If the name rings a bell, it’s because this spot serves as one of the coast’s biggest fish exporters, making most of the meals literally “fresh off the boat.” The menu can be overwhelming with so much to choose from, but classics like conch fritters with remoulade, peel-and-eat Key West shrimp, and Dottie’s smoked fish dip are good starts. Don’t miss the Key Largo lobster BLT and Key Largo Lobster Philly.

Come for the nightly sunset celebrations overlooking idyllic Florida Bay and listen to local bands while sampling favorites like Stone crab chowder, Key lime peppercorn snapper, and twin lobster tails. Don’t pass on Lorelei’s World Famous “Frozen” Key Lime Pie for dessert, which is less tart than standard key lime pie and comes topped with mango sauce and whipped cream.

Chef Michael Ledwith honed his culinary skills at some of New York’s top spots before being lured to Islamorada’s laidback lifestyle. Diners are privy to upscale seafood specialties in this New American hotspot —many of which are sourced fresh from the Keys each day. Other options include conch bisque, roast duck with mango and mandarins, and filet mignon with smoky bacon and gorgonzola cream.

Fuel up with every kind of good coffee imaginable (hot or iced), freshly-baked muffins, and morning staples like Everiyone’s Favorite Sandwich (croissant with scrambled eggs, cheddar, and bacon), the breakfast burrito, or avocado toast. There are lighter items like smoothies and lunch items as well.

Slip right into the Keys groove with a tiki drink and seafood favorites like mango crabcakes, stuffed shrimp, and Florida lobster tail. The menu is massive and accommodating to everyone, whether you want steaks, pasta, chicken, or a vegetable burger. Like most spots, there’s Key lime pie on the menu, but more intriguing is the deep-fried rendition, which is rolled in cinnamon sugar and drizzled with mango sauce.

Beer lovers, take note: there are 52 beers on tap to go along with this restaurant’s expansive menu. Founded in 1951, it was originally the place to stop for a beer and shrimp steamed in beer, that is, until John Mirabella and his wife Arlene sailed from Los Angeles to the Keys purchasing the restaurant in 1999 and expanding the menu to include offerings like oysters Moscow (raw oysters on the half shell served with sour cream, horseradish, and red and black roe) and snapper BLT (fried yellowtail snapper, bacon, chipotle aioli sauce) and, of course, shrimp steamed in beer.

Tucked inside the Sugarloaf Lodge, owners chef Paul Kapsalis and Kris Kubik serve modern American fare like spiny lobster and Key West pink shrimp bisque, golden tilefish with blue crab, and shrimp and lobster cannelloni. Carnivores are not forgotten either, with the menu boasting a generous selection of meat dishes like the 40-ounce Tomahawk steak, filet mignon topped with blue cheese, and 20-ounce T-bone steak.

Several outlets throughout town make it easy to get a regular caffeine fix, breakfast sandwiches, and plenty of merch like t-shirts with cheeky messages like “Drink More Cuban Coffee and Do Stupid Things Faster.” Coffee is available for purchase by the pound, which means the caffeine party can continue at home.

Epitomizing the relaxed vibe of Key West, this colorful venue made from driftwood welcomes diners with a junk car swathed in bumper stickers. The menu is a straightforward array of fresh seafood caught from the docks a few blocks away, along with the prerequisite burger. The fried conch sandwich is a must, as is an order of gigantic onion rings.

This local favorite is the ideal brunch spot within walking distance from all the action on Duval. Grab a table on the lush outdoor patio and indulge in Key lime French toast (yes, there’s pie in there!) and the crab cake Benedict served on a flatbread or Roesti potato pancake with brie, prosciutto, arugula, and hollandaise.

This tiny corner grocery has been doling out some of the best Cuban sandwiches and Cuban coffee for several generations. There’s the traditional Cuban sandwich, or better yet, the Cuban mix (ham, pork, salami, swiss cheese, lettuce, tomato, and pickles.) Feel like ending the meal with a cigar? No worries, 5 Brothers sells those too.

A meal here will leave diners feeling like they’ve stumbled upon a gem or little pearl. Dishes are thoughtful and well executed, with a rotating tasting highlighting locally caught seafood, among other items. Wine pairing is also available. Reservations required.

Just two blocks from Key West’s Southernmost Point, diners will find this warm spot run by husband and wife team chefs Kevin Montoya and Maggie Montoya. Serving a range of flavors, dishes include sherry mushroom soup, pan-seared hogfish, and sage-roasted pork loin; it’s an excellent spot for an elevated meal before heading to rowdy Duval street.