Gilbert’s

Overview

Gilbert’s is the classic first-stop in the Upper Keys: a beachfront resort with a big tiki bar, sandy seating, and uninterrupted sunset views over Blackwater Sound. Expect a casual, social scene—cold drinks, seafood, and live bands with the water as your backdrop.

Why go

• Sunsets are the headline act, and the show is straight ahead from the beach and tiki bar.
• The vibe leans easygoing Keys: shoes optional, music up, and plenty of people‑watching. Dolphins sometimes cruise by while you’re eating or sipping a drink.

Food & drink

The menu hits the Florida Keys greatest hits—seafood plates, sandwiches, wings, steaks—and a raw bar. Cocktails are a strong suit, and the tiki setup makes it easy to linger for a long lunch that rolls into golden hour.

On the water

There’s a full marina and fuel dock, plus on‑site rentals for jet skis, paddleboards, kayaks, and boats if you want to turn a meal stop into an afternoon on the Sound. Boaters can pull up to the dock and come ashore for food and drinks.

Cabanas & stays

Day cabanas add shade and server attention for a hang‑all‑day setup. If you’re not leaving, the resort offers simple, waterfront motel‑style rooms, a private beach area, and a pool—handy if you want to base here instead of just passing through.

What to expect

Crowds build fast on weekends and around sunset; that’s part of the fun, but it does slow service. Parking is free, but the lot and nearby street spots fill when the band is playing.

Best time to visit

Aim for weekday late lunch into sunset for the sweet spot of easy parking, music, and light. On weekends, arrive before mid‑afternoon to snag a table; the rush peaks from early afternoon through sunset. Golden hour is the money time for photos across Blackwater Sound.