This old blue building was a witness to a little bit of everything in its century-old history. It’s been an artist commune, an ice cream parlor, a gambling house, and a brothel, not necessarily in that order. But now, Blue Heaven is credibly the most laid-back fine-dining restaurant you may ever see. Don’t miss breakfast-eggs Benedict with lobster and key lime hollandaise. Key West shrimp and grits, and banana bread — that’s its own little slice of paradise.
located at Thomas St.
Tucked away in the center of Old Town, this unpretentious family-owned dining place is know for its good Cuban food. Your meal commences with butter-soaked Cuban bread piled high in a red plastic basket.
You then order numbered dishes such as “1. Roasted Pork” or “24. Breaded Shrimp.” Yellow rice, black beans, and sticky sweet plantains crowd every plate, perfectly paired with the homemade sangria.
located at 900 Catherine St.
The food is as fantastic as the scenery at this transformed oceanfront property on Waddell Avenue, which also boasts of having one of the finest views on the island. Chef Doug Shook joined the staff twenty-four years ago, and his talent has established Louie’s as stand out favorite. The nightly specials reflect the fresh seafood gathered at the dock that day, which inludes grouper, snapper, swordfish, shrimp, and lobster, depending on the season. To add, the lower deck is a perfect spot for a happy-hour cocktail.
located at 700 Waddell Ave.
Key West resembles a bit more of Little Havana than Little Italy, but don’t let that deter you to stop at Mangia Mangia (“Eat! Eat!”). The trattoria’s marinara sauce and semolina pasta are freshly-made daily, though you’ll also find some innovative nods to local tradition (like the conch minestrone). Get ready to choose from the forty-four-page wine list that will blow your mind.
located at 900 Southard St.
Big flavors come in small sizes at Santiago’s, a tapas restaurant situated in one of Key West’s oldest neighborhoods, Bahama Village. Heavenly salads and plates like yellowfin ceviche or prosciutto-wrapped dates match well with a fine selection of beer, wine, and ports. The tiny place gets filled up quick every night, so reservations are strongly advised.
located at 207 Petronia St.