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 includes 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 a 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.” With so much to choose from the menu can be overwhelming but classics like conch fritters with remoulade, peel and eat Key West shrimp, and stone crab chowder (when in season) are good starts. Don’t miss the lobster reuben, which like the original reuben comes served on toasted rye bread with sauerkraut, Swiss cheese, and Thousand Island dressing swapping corned beef with a generous serving of lobster.

Come for the nightly sunset celebrations overlooking idyllic Florida Bay and listen to local bands while sampling favorites like Lorelei’s smoked fish dip, 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.

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 aoili 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 Apalachicola oysters roasted in their shell with chorizo, manchego, garlic butter, cilantro, and lime and locally-caught whole fish fried Thai style. Carnivores are not forgotten either with the menu having a generous selection of meat dishes like the 40-ounce Tomahawk steak, ribeye steak, and Sugarloaf burger.

Several outlets throughout town make it easy to get a regular caffeine fix along with 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 simple and 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.

Within walking distance from all the action on Duval, this local favorite is the ideal brunch spot. Grab a table in the lush, outdoor patio and indulge in Key lime French toast (yes, there’s pie in there!) as well as the crab cake benedict served on 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 as if they’ve stumbled upon a gem, or little pearl. Dishes are thoughtful and well executed, with a tasting menu currently in place featuring items like crab and mushroom bisque, garlic black pepper prawn, and swordfish with sesame soy broccolini, fingerling potatoes, and miso brown butter. End with a cheese plate or moscato ginger and poached pear. Wine pairing is also available. Reservations required.

Known as one of the top brunch spots in town, this Key West staple offers bites like Florida shrimp omelet or Blue Heaven BLT benedict (bacon, lobster and tomato). Sit in the courtyard where chickens and cats roam free.