Jamaica Inn in Ocho Rios, on the north coast, was frequented by Marilyn Monroe, Ian Fleming and Sir Winston Churchill. Step straight on to the beach from your suite (there are 52 suites and cottages in total) and order a rum punch from Teddy, the legendary 75-year-old, who has been running the bar here for 59 years. For a more boutique experience, try the Rockhouse hotel, which sits on the cliff face of Negril. With totally tropical sunsets, pools nestled in the rocky cliffs and suites housed in individual huts, it’s barefoot bliss at its best.