The Caribbean of yesteryear—before the clunky beachfront high-rises, jet-choked airports, and comically sized cruise terminals—is not so easy to locate. In most cases, it requires memberships to clubs such as Tryall, Lyford Cay, or Mill Reef, or an invitation to a private home—preferably one that’s been in the family for generations.

The beach at Port Antonio’s cruise pier, near Goblin Hill.

But Goblin Hill, which abuts the idyllic San San Bay, in Jamaica’s Port Antonio parish, is a little bit of both. It’s clubby, as it was originally built as a condominium development by a few couples from Kingston who fancied a weekend escape. And it’s private-ish, as it’s still owned by co-founders Rosalie and Marvin Goodman and frequented by many of the same families.