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Winter Sun in Jamaica: A Couple’s Retreat at Round Hill

Montego Bay

Set a secluded 100-acre peninsula once blanketed in pineapple groves, Round Hill in Montego Bay remains one of the Caribbean’s most iconic hideaways. A place where history lingers in the breeze and luxury whispers rather than shouts.

Stay in one of the Pineapple House’s ocean-view rooms, curated by long-time resident Ralph Lauren. With warm Jamaican hospitality, elegant dining, and postcard-perfect views, it’s the ultimate winter sun escape.

Best time to travel: November – April
From price: €4,499 per person

What's Included

  • All international flights and private transfers.
  • 7 nights’ luxury accommodation in Montego Bay.
  • Spend time unwinding on the beach and taking part in a selection of water sports and land activities available in-resort.
  • Enjoy dining with sensational views, sampling authentic Caribbean cuisine using local ingredients.
  • Allow us to arrange tailored experiences like a private chef’s lunch and horse riding on the beach.

Hand-Picked Accommodation

7 nights in Round Hill Hotel & Villas, B&B basis.

We will suggest the best room type and board basis depending on your preferences.

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