If there’s one off-season locale Naples locals look forward to, it’s Watermark Grille, just off Tamiami Trail. This longtime, family-run spot, run by two brothers for over 25 years, has that rare mix of consistency and old-school charm that’s getting hard to find.

The headline here is the off-season special: a 2-pound Maine lobster for $39.99, served with garlic mashed potatoes and broccolini. In a town where the ever-elusive price “MP” shows up more than actual numbers, it feels like a steal. The lobster is sweet, hefty, and more than worth it, even if they’re not budging on side substitutions.

And if lobster’s not your thing, you’re still in good hands. Watermark has classic steakhouse comforts like prime rib, filet, and French onion soup, in addition to seafood offerings like scallops and coconut shrimp. The lobster-averse can’t go wrong with the steak.

The space is a true ‘90s throwback and largely unchanged since it opened in 1998. Think curved dining room, indoor palm trees, water features, and colorful lighting. Some call it dated, but for many, that nostalgic charm is exactly what keeps them coming back.

Watermark is quintessentially Naples and somehow feels even better in the off-season. Plus, supporting a local, family-run spot always makes the meal taste a little better.

11280 Tamiami Trl N, Naples, FL 34110  | watermarkgrille.com  | Sun–Thurs 4–9 p.m. Fri–Sat 4–10 p.m. | (239) 596-1400

Originally published in
The Naples Florida Review.
Read the full edition here.