Our Beginning

Gregory Callwood, proprietor, was born and bred on Jost Van Dyke. He has two children, Zephaniah and Olivia Callwood. Greg’s wife, Hilda is his partner and head chef and ambassador of hospitality. Greg is devoted to promoting and taking care of Jost Van Dyke. He’s active in the Jost Van Dyke Action Committee, the BVI Tourist Board, and the JVD Taxi Association.


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He’s also been instrumental in promoting musical entertainment events at the Perfect Pineapple Inn.
Once you stay at the Perfect Pineapple Inn and enjoy Greg and Hilda’s Caribbean hospitality, you’ll know why nothing should change on Jost Van Dyke.

The Building of Perfect Pineapple

As the story goes, after Hurricane Marilyn in 1985, Greg lived in a wooden house and rode the Hurricane out under some very hard conditions. After this, he decided to build a concrete house to use for shelter. This is now room 3, but then it was designed to protect him and his family.

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However, after building it, he never used the concrete shelter as a hurricane shelter, but decided to rent it out. He always wanted to be an Inn keeper, a dream he had growing up. Having success renting out Room 3, he built two more rooms at the turn of the century in 2000. Finding a name came easy, it goes right in with his philosphy of life and doing business — perfect pineapple — pineapple means hospitality and welcome!