In the game
Trailer 2 has a scene fans returned to more than almost any other: a waterfront bar in the Keys at the golden hour, thatched roof, string lights, boats tied up outside, drinks in hand. It’s the Leonida Keys at rest, and it looks very much like the kind of place Jason, who lives down here, would spend his evenings.
Fans have matched it to the bayside tiki bars of Islamorada rather than to any single bar, and that feels right. The elements are generic on purpose: palapa roof, tables on the sand, a dock, the sun dropping into flat water to the west. Only the bayside of the Upper Keys gives you that exact sunset over water from a barstool. Rockstar hasn’t named a bar, and we’re not going to guess for them.
The real place
Islamorada calls itself the sport-fishing capital of the world, and the bars grew up to serve the boats. The tiki bar as a Keys institution dates to the 1950s and 60s, when thatched-roof chickee bars started appearing at marinas; the Rum Runner cocktail was invented at the Holiday Isle tiki bar here in the early 1970s.
Standing at one today you’ll get, roughly in this order: a mermaid or a marlin on the sign, a floor of sand or crushed shell, a band playing Buffett covers, a menu of fish sandwiches and conch fritters, and a crowd that slowly turns to face west as the light goes orange. The detail a GTA fan will recognize is the dock, right there, with boats nosing in for a drink. In the Keys people arrive at the bar by water, which is precisely how the trailer frames it.
Go there
Two bars cover it. Lorelei Restaurant and Cabana Bar (MM 82, bayside) is the classic sunset spot: giant mermaid sign, tables on the beach, live music most nights. Robbie’s of Islamorada (MM 77.5, bayside) is the other essential, part marina, part bar, part flea market, with the Hungry Tarpon restaurant on the dock and a hundred tarpon waiting underneath it to be hand-fed. Feed the fish first, then eat.
If you want the historic one, the tiki bar at the Postcard Inn at Holiday Isle (MM 84, oceanside) is where the Rum Runner was born. Check it’s open before you go; the resort has been through several renovations.
Plan to arrive 60-90 minutes before sunset. Tables on the water go first, and there’s usually no reservation system for the outdoor areas. Bring cash for the tip jar if there’s a band.
One honest warning: this is US-1, a two-lane road with no street lights, and the drinks are strong. Islamorada is small enough that a rideshare or a taxi back to your hotel is cheap, and DUI enforcement on the highway is serious. Don’t drive after a sunset session.
Nearby
- Betsy the Lobster: five minutes north for the photo before the drinks.
- The mangrove backcountry: book a morning kayak or flats trip from Robbie’s, then reward yourself here.
- Canal homes of the Upper Keys: the neighborhoods behind the bars are where the boats live.
Updated September 12, 2026. Spotted an error? Tell us.