Direct Flights to Key West, FL

Since the first location opened almost a decade ago (they now have four locations across the island, including one in the shops right next to Opal Key), Cuban Coffee Queen has become something of the Starbucks of Key West: You can’t walk down the street without bumping into someone with a cup of their traditional Cuban coffee drinks in hand. While on the island, trade in your caramel macchiato for a cortadito, a double shot of Cuban espresso with cane sugar and steamed milk, or an ice-cold Cuban frappe.

You have two alfresco eating options at Latitudes at Sunset Key Cottages: to sit under the patio’s extended eaves or right on the sand surrounded by low hedges, palm trees, and a breathtaking backdrop of the Gulf. The lunch menu is certainly nothing to scoff at either, offering everything from wyagu burgers to fresh and flavorful marine-inspired masterpieces like the yellowtail snapper served with saffron rice and roasted tomato caper butter.

Located on Greene Street, The Breakfast Club Too is a quirky local favorite known for its playful, treasure chest–themed bar and serving up the best Bloodies in town. Choose from 12 different iterations, including a scotch version, an extra spicy version, a BBQ version, and the Monster Mary which is served in a quart-sized mason jar.

The brand-new signature restaurant of Opal Key Resort & Marina, Lolita’s Coastal Cocina offers an elevated take on coastal Mexican cuisine with stunning waterfront views. Blending shareable plates – like guacamole flights, ceviches, tacos, and lobster enchiladas – with a curated tequila and mezcal list and, the space features colorful folk-inspired décor both indoors and alfresco, capturing a laid back yet stylish vibe unlike anything else in Key West.

Duval Street’s Bagatelle is a charming, historic-conch-house turned restaurant that delivers refined yet relaxed dining. The menu reflects a fresh American-Caribbean flair, with standout dishes like blackened swordfish, whole fried snapper, lobster mac ’n’ cheese, and Filet Mignon – all heightened by two daily happy hours and an extensive wine list.

Located on Caroline Street near the Historic Seaport, Harpoon Harry’s is a Key West breakfast institution serving hearty comfort food and made-from-scratch classics all day long. With a lively, diner-style atmosphere, cash-only policy, and a fully stocked bar, it’s celebrated for highlights like Key Lime Pie French Toast, Crab Cake Benedict, and their signature Bloody Harry cocktails.

With its funky, artsy vibe dotted with wandering chickens and cats, Blue Heaven feels more like a backyard barbecue than a restaurant. The al-fresco lunch destination set in the Bahama Village of Old Town serves a casual menu of Jamaican jerk chicken, fresh local seafood, and a mouthwatering mound of a burger. Still, the most eye-popping dish to come sailing out of the kitchen is the key lime pie with a towering pile of meringue.

Elevate Skye Bar & Lounge at Opal Key Resort & Marina is a new, open-air rooftop dinner spot that’s quickly becoming a favorite for sunset seekers. With panoramic marina views, it offers a laid-back yet sophisticated vibe – think handcrafted cocktails, shareable small plates (like ceviche and BBQ short rib tacos), and breezy island ambiance. Whether you opt for a ginger pear martini at twilight or pairing mojitos with an artisan cheese board, it’s the best place for sipping at sunset.