1Strawberry Hill: Does this hotel have the best pool in Jamaica? We’ll let you decide: its infinity edge reaches right out over a mountainside, where a sweeping view of Kingston spreads out below. Record producer Chris Blackwell (also behind The Caves in Negril and GoldenEye in Oracabessa) modeled everything at this 13-room reprieve after the colonial Jamaica of the 19th century, with Georgian-style timber cottages that retain colonial charm—plantation shutters, mahogany four-poster beds, private verandas overlooking the misty mountainside. Blackwell is the reason why this spot has secured a place in music industry lore (Bob Marley, Sting, and Mick Jagger have all stayed). Check out the Gold Room to see records and awards for Blackwell’s work with greats like U2 and Bob Dylan.

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