The Florida Keys, FL, Decided.
Every decision that matters, on one page.
✦ Stay: Little Palm Island Resort & Spa ($$$$)
✦ Eat: Louie's Backyard — book days-to-weeks in high season — reserve dinner ahead (especially Dec–Apr and for sunset-adjacent seatings). The play: book a table on or near the oceanfront deck for the Atlantic view; if you can't get a table or want casual, the Afterdeck Bar takes walk-ins for waterfront drinks + a lighter menu.
✦ Stay: Isla Bella Beach Resort ($$$-$$$$)
✦ Eat: Keys Fisheries Market & Marina — book walk-in — order at the window (they'll call a funny name when it's ready) and grab a marina-side picnic table; no reservations. The play: come for the lobster reuben (the signature) and, in stone- crab season (~mid-Oct–early May), the stone crab claws; go off-peak to skip the window line.
✦ Stay: Hawks Cay Resort ($$$-$$$$)
✦ Eat: Blue Heaven — book walk-in — breakfast and lunch (8:00am–2:30pm) are FIRST-COME with no reservations; the play is to arrive early (near opening) to beat the high-season line, especially on cruise-ship days. Dinner (5:00–10:00) takes walk-ins plus a limited number of phone reservations — call ahead for dinner if you want a held table. Expect a wait at peak breakfast; it's part of the experience.
✦ Stay: Ocean Key Resort & Spa ($$$$)
✦ Eat: El Meson de Pepe — book walk-in — it's a large, high-turnover spot built for the Mallory Square crowd; no reservation usually needed, but sunset hour + cruise-ship days are the busiest, so arrive a bit before the Sunset Celebration if you want a patio table timed to the light. Larger groups can call ahead.
When to go: December, January, March, April.