Naples, FL, Decided.

✦ Stay: Naples Beach Club, A Four Seasons Resort ($$$$)

✦ Eat: The Turtle Club — book weeks in high season — the sunset seating is one of Naples' most in-demand tables. The play: reserve online (Tock) or by phone (239-592-6557) as far ahead as the book allows, and target a seating ~60–90 min before sunset for the light. IMPORTANT: a reservation gets you a table, but OUTDOOR beachfront tables are first-come/not-guaranteed — arrive early and ask, and have a plan B if the toes-in-sand row is full. Dining is reportedly capped ~2 hours.

✦ Stay: Inn on Fifth ($$$-$$$$)

✦ Eat: bha! bha! Persian Bistro — book days-to-weeks in high season — a small, very popular Fifth Avenue bistro; reserve on OpenTable ahead. The play: book dinner and order the lamb shank + flash-fried eggplant (the signatures); it's the "something different" night in a town heavy on Italian and seafood.

✦ Stay: Edgewater Beach Hotel ($$$-$$$$)

✦ Eat: Molto Trattoria — book Reserve via Resy or OpenTable. In high season (Jan–Apr) book several days out for a prime dinner slot on Fifth Avenue South; shoulder/off-season walk-ins are more forgiving, especially at lunch.

✦ Stay: The Ritz-Carlton, Naples ($$$$)

✦ Eat: Violí — book days-to-weeks in high season — reserve on OpenTable ahead, especially for a group. It opens daily at 3pm for happy-hour "boukia" (light bites), and runs a 3-course dinner Sun–Thu 3–6pm; the play is a long table and shared plates. Confirm current hours on site.

✦ Stay: The Ritz-Carlton Naples, Tiburón ($$$$)

✦ Eat: Baleen — book days-to-weeks in high season — reserve ahead (via the resort / OpenTable) and target a table ~60–90 min before sunset for the Gulf view. IMPORTANT: confirm current on-site construction status at LaPlaya for your dates (see the hotel entity) — the beachfront setting is the whole draw and it should be verified before you build the evening around it.