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.

Serving freshly caught fish sandwiches and drinks like the Islamorada Ice Pick (ice tea vodka, lemonade, and a splash of champagne) overlooking turquoise waters, this spot knows how to get the vacation vibe going right away. Afterwards, head over to feed the tarpon where more than 100 of the large fish will grab bait almost out of one’s hand.

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 simply 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.

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.

A little removed from the party scene on Duval Street, this peaceful American restaurant inside the Perry Hotel Key West is offering some of the best meals on the island. Self-described as American coastal comfort food, appetizers like the crab beignets with lemon powder and stone grain mustard aoili and the oyster Rockefeller with parmesan, kale, bacon, and anise are not to be missed. Grouper gnudi (gnocchi-like dumplings made with ricotta) or shrimp and grits with tomato bacon gravy and manchego cheese are both must-try dishes.

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.

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.

Primarily a seafood market for the locals, this spot also serves one of the best lobster rolls south of Maine. The secret is the lobster-to-bun ratio. While many lobster rolls are guilty of overdoing it with carbs, here, diners are treated to a tidy, buttery, toasted bun generously packed with chilled lobster salad heavy on the lobster meat. There’s no real seating inside, so grab it to go or snag one of the spots outside.

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.

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.