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Main Street Restaurant – Bringing the world to your table


Initiative, creativity, and spontaneity drive the unique dishes that Main Street Restaurant brings to Road Town on a weekly basis. From oxtail tacos to seafood jambalaya, there’s rarely a set menu that customers can expect, and owner Kai de Castro says it’s to keep people on their toes.


The menu is designed to keep fresh local ingredients including catch like snapper and tuna, and also to keep it simple and easy. From lasagna to burgers, grilled steak to pizza, customers can find a variety of offerings every day of the week.

It’s de Castro’s perspective that’s helped shape the vision for the restaurant, which opened in August. As a belonger, he studied civil engineering in Florida and traveled throughout Europe and the Caribbean to islands like St. Kitts, St. Lucia, and Dominica to see how the world worked. He came to realize that “every country has its own niche” and its own way about it.

By taking the unique qualities and traits of the Virgin Islands and mixing that with qualities found all over the world, de Castro has painstakingly built Main Street Restaurant.


When you first pass by Main Street Restaurant, it’s a bit of a shock: the brightly colored orange exterior complemented by dark wooden shutters and contrasting silver hinges give way to the neatly framed sign with the restaurant’s name. Notable is the old-fashioned post office sign tucked into the logo, bearing “Q II E” for the late Queen Elizabeth II.

It’s this historical touch that Kai de Castro has worked so hard to bring to fruition since he first began construction at the site in 2019 – and he can pinpoint exactly what inspired him to do it.

“I went to Portugal, and I Googled “the best place in town,” and it was this old little vintage breakfast spot somebody’s grandma opened,” he said. “I went to other places like Belgium, Spain and again, it’s the same feeling — they take the town, and they create an atmosphere.”


He took his 100-year-old family property, which was built in 1920, and decided to create something that would withstand the test of time on it.

“I did it because I want to say, ‘Okay, the building has been here for 100 years. I want the restaurant to be here for 100 years,” he said.

Badly damaged in hurricane Irma in 2017, the process was long and took diligence. It was de Castro’s five-year plan to bring “a little bit of Tortola, a little bit of the BVI, a little Caribbean” to the area.

Walking into the entrance you’ll find an original post office box that used to be found throughout the Virgin Islands, something only sharp-eyed individuals will glimpse remnants of in remote corners of the island. This one’s been done up — its vivid blue paint is something difficult to avoid, whether you’re just strolling by or interested in a bite.

The first of four seating areas is an outdoor patio featuring a calming wall of succulents and greenery. A larger table of six can be seated there comfortably, but smaller and more intimate groups of four or two can also have tables on the patio. A fully stocked open bar also has seating for those who want a cold one and an outdoor ambience closer to the ground. Come upstairs, through the main doors, and an entirely different atmosphere opens up.

Neatly pressed brown tiles frame a well-lit bar area, where waitresses and waiters have an arrangement of spirits and exactly the right dinnerware to serve them in. Casual music fills the area, where swivel chairs line the bar front and small tables line the walls. Home country pride and heritage are displayed on the walls with license plates, offering a slightly grunge aesthetic in an otherwise elegant environment.

Adjacently, a room filled with high leatherback booths and small tables with leather chairs gives a cozy dinner environment. Crimson red napkins holding silverware are placed at each table, popping up against the neutral brown and black furniture.

Another patio — this one overlooking the street — welcomes the sounds of historic Main Street and views of the colorful buildings around. The patio is filled with highchairs and glass tables.

Patrons come into and out of the establishment, often picking up their lunchtime meals passed through the open bar area.

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