From Cayman to the Keys – Dockside Raw Bar & Grill

Angel Borden dreaded the drive to the Keys as a child. Though she loved the destination, she was terrified of the Seven Mile Bridge. Surrounded by water on a narrow stretch of road made her stomach clench. 

Despite many stomach-aching trips to the Keys, Angel enjoyed island life and was drawn to island people. Her husband John grew up in Islamorada, but his family was from the Cayman Islands, and Angel eventually followed him back to his homeland from her home in Montana.

Angel was impressed by Cayman’s beauty and competitive school system. She decided it was where she wanted to raise her children, two of which were born there. The esteemed school system did its job, as all four of her daughters have grown into successful adults.

But before one daughter was grown, Angel faced an unexpected problem when her 14-year-old daughter became stranded in Florida. Angel had sent her on a 3-day cruise with her friends, not realizing that her Cayman passport and visa waiver only allowed a one-way trip. The cruise line would not allow her daughter to board the ship.

Not knowing who else to call, Angel reached out to her husband’s old friend, Jorge Cabrera, who grew up and lived in the Keys. Jorge picked up Angel’s daughter and brought her to his house to stay with him and his mother. This reconnection between Jorge and Angel grew into a deeper friendship and eventually more.

After her daughters were off to college, Angel grew weary of living on an island with nowhere to go. She started to wish for a bridge that would allow her to stretch her legs beyond the Cayman shores. Jorge asked her to join him in the Keys in February 2011, and she agreed.

They started to build a new life together, first with Angel helping with Jorge’s roll off dumpsters and a cardboard recycling business. Changes in international trade policies caused those businesses to fail, but they had already established Old Conch Harbor, Inc. by that time. Jorge planned to open The Chart Room on the second floor, while Angel would have her own restaurant on the first floor.

Dockside Raw Bar & Grill opened in 2021 under the direction of Jorge, as 3 of Angel’s daughters gave her 3 granddaughters within 12 months, keeping her busy with out-of-town visits. Their goal was to cater to locals and bring back “how the Keys used to be.” 

“We treat guests great,” Angel says, “but we treat locals even better.”

Backing up her words, Dockside Raw Bar & Grill gives a 10% discount to locals. It’s part of her buy local, support local business model, which also includes serving local brews on tap.

Angel is also a member of the Chamber of Commerce and the Matacumbe Historical Trust. She has held events at Dockside, including the Coralpalooza in June, where they served 180 dinners. They also provide kayaks for the Swim For Alligator Lighthouse.

Mark Brown, who was raised in the Keys, helped Angel revamp her menu last September. His dad trained dolphins and birds at Theater of the Sea, which came in handy for Angel. Her rescue parrot wasn’t friendly until Mark used what he learned from his father to transform Big Bird into a friendly mascot for the bar.

In addition to serving fresh, local catches and homemade grilled food, Dockside hosts the IDP Podcast every Friday, that’s like the “Cheers of the Keys.” It showcases local musicians, and any guest can join in. 

One year after the bar opened, Jorge succumbed to diabetes, breaking Angel’s heart but not her spirit. She is continuing their dream of making Dockside Raw Bar & Grill a place “for locals by locals.”


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