Jack's Lookout

Waterfront Dive Bar

Pop open a cold one

Jack’s Lookout is a classic dive bar frequented by locals and visitors alike who come for unobstructed views of the marina. The food menu is limited to very simple items like hotdogs and chilli cheese dogs and the beverage menu is just as small with beer by the can and few wine options.

But the star of the show is obviously the view. Guests can sit back, relax and watch the birds at the harbor or fisherman practice their trade. Multiple reviews recommend guests come at around 1:00 p.m. or 3:00 p.m. to watch the fishing boats come in. Naturally, the bar and the surrounding area will have a very dominant fish smell.

Shabby Chic?

The inside seating area is decorated with memorabilia regulars bring in from all over the world. This gives the small bar a unique and friendly environment which encourages strangers to chat with each other. Many reviews highlight the “black hole of time lost” nature of the bar as guests pop in for a quick beer or a bite to eat, but end up staying for hours.

Guests can also use Jack’s Lookout as a starting point to get to Key West or hang out while their boat is refueling at the marina.

The Sun King’s Review of Jack’s Lookout

You’re vacationing on an island to immerse yourself in the island vibe, right? You want to escape the fast-paced, stress of your everyday life and really relax. Jack’s Lookout is the place to go. Sip a cold whatever overlooking the water and the boats. The Sun King gives Jack’s two thumbs up.