Strawberry Hill

High in the Blue Mountains above Kingston, Strawberry Hill is a small luxury retreat of Georgian-style cottages and villas, part of Chris Blackwell’s Island Outpost group. Panoramic views reach over Kingston to the sea, alongside an infinity pool, a spa, a restaurant and a bar — and noticeably cooler air once the sun goes down.

Bob Marley stayed here after he was shot in the 1970s, and the property still trades on quiet, views and mountain time rather than a beach — hikes and coffee-estate visits are the draw, reached via a winding drive up from Kingston. (Note: this is a different property from Blessings at Strawberry Fields in Robins Bay, St Mary.)