St. Augustine, FL, Decided.

✦ Stay: Casa Monica Resort & Spa ($$$-$$$$)

✦ Eat: Columbia Restaurant — book same-day-to-days — it's large and takes reservations (OpenTable) but fills at peak times and in high season; reserve for a prime dinner or arrive off-peak. The play: the tableside 1905 Salad + sangria + paella, in the palm-and-tile room; a dependable group/family choice on St. George Street.

✦ Stay: St. Francis Inn ($$-$$$)

✦ Eat: The Floridian — book same-day-to-days — a popular local spot with waits at peak times; reserve or arrive off-peak. The play: the seasonal creative-Southern menu (shrimp & grits, fried green tomatoes, veg-forward plates) — one of the best vegetarian/vegan-friendly tables in town. Confirm reservations policy on site.

✦ Stay: Embassy Suites St. Augustine Beach Oceanfront Resort ($$-$$$)

✦ Eat: O'Steen's Restaurant — book no reservations, CASH ONLY — the plan is to beat the line. Arrive ~10:45am or right at 4–4:30pm, or order TAKEOUT (ready in ~10 min) to skip the dining-room wait. Closed Sunday + Monday; closes 8:30pm. The play: the fried shrimp (the local legend), plus fried/broiled seafood plates and Southern sides.

✦ Stay: The Collector Luxury Inn & Gardens ($$$-$$$$)

✦ Eat: Collage Restaurant — book days-to-weeks — with only ~15 tables it books out, especially weekends and high season; reserve ahead (OpenTable). The play: the occasion dinner of the trip — local seafood/steak/lamb with an international bent, in an intimate room. Dress up a little.