Anna Maria Island, FL, Decided.

✦ Stay: Waterline Villas & Marina, Autograph Collection ($$$-$$$$)

✦ Eat: The Waterfront Restaurant — book days (more in high season) — it's a small, popular room, so reserve rather than risk a wait. The play: book an earlier or later seating to dodge the peak crunch; pair with a Pine Avenue stroll and the City Pier area at the north end. Confirm current reservation channel + hours on site.

✦ Stay: Tortuga Beach Resort ($$-$$$)

✦ Eat: Beach House Waterfront Restaurant — book days-to-weeks in high season — like its sister the Sandbar, the sunset seating is in heavy demand. The play: reserve online (OpenTable) ahead and target a seating ~60–90 min before sunset; the climate-controlled deck is the weather-proof option, the sand tables the toes-in experience (first-come). Pair with a Bridge Street / Coquina Beach afternoon at the south end.

✦ Stay: Anna Maria Beach Resort ($$$)

✦ Eat: Ginny's & Jane E's — book walk-in — a casual daytime bakery-cafe; go for breakfast or lunch and expect a line at peak. The play: come for the character (the old grocery-store setting + antiques) as much as the food; grab a pastry and coffee and browse. Confirm current hours on site (bakery-cafes keep daytime hours).