Nestled along the picturesque coastline of Montego Bay, Jamaica, Round Hill stands as a timeless retreat offering a blend of luxury, history, and warm Jamaican hospitality.

This boutique resort, originally founded in 1953 by Jamaican entrepreneur John Pringle, has become synonymous with elegance and sophistication, attracting discerning travelers seeking an authentic Caribbean experience.

Set the Scene: As you arrive at Round Hill, you’re greeted with the tranquil ambiance of a secluded paradise. The lush greenery and expansive grounds create a sense of serenity, inviting guests to unwind and immerse themselves in the natural beauty of the surroundings. Friendly staff members engage guests with genuine warmth, fostering a sense of community and camaraderie among visitors.

The Backstory: Founded over half a century ago, Round Hill has a rich history steeped in glamour and prestige. Once frequented by celebrities and dignitaries, including John F. Kennedy and Paul McCartney, the resort retains an air of sophistication while maintaining its laid-back Caribbean charm. The Grill, adorned with framed black-and-white photos of notable guests, serves as a testament to the resort’s illustrious past.

The Rooms: Round Hill offers a variety of accommodations, ranging from the chic rooms in the Pineapple House to the spacious villas scattered across the property. Designed by Ralph Lauren himself, the rooms exude timeless elegance with clean white interiors and crisp navy and pink accents. Whether you opt for an Ocean View room or a luxurious villa, each space offers a comfortable sanctuary with stunning views of the Caribbean Sea.

Food and Drink: Dining at Round Hill is a culinary journey infused with the flavors of the Caribbean. The flagship restaurant, designed by Ralph Lauren, showcases fresh Caribbean cuisine sourced from the resort’s organic gardens. From jerk mac n’ cheese to oxtail ravioli, each dish is a celebration of local ingredients and traditional recipes. Guests can also enjoy casual dining options at the Seaside Terrace or indulge in afternoon tea featuring housemade biscuits and local teas.

The Spa: For ultimate relaxation, guests can visit the spa housed in an 18th-century plantation house overlooking the sea. Treatments range from massages to facials, offering a blissful escape from the hustle and bustle of daily life. Fitness and yoga classes are also available, led by charismatic instructors like Donovan, adding to the rejuvenating experience.

The Neighborhood/Area: While Round Hill offers a tranquil retreat within its lush grounds, adventurous guests can explore the nearby attractions of Montego Bay. From rum distillery tours to ziplining at YS Falls, there’s no shortage of activities to experience the vibrant culture and natural beauty of Jamaica.

The Service: Round Hill prides itself on its exemplary service, with many staff members boasting decades of experience. The warm and friendly hospitality ensures that every guest feels welcomed and cared for, creating a memorable and personalized experience.

For Families: Round Hill is the perfect destination for families, offering a range of amenities and activities for all ages. With a dedicated kids’ club, water sports rentals, and expansive grounds to explore, children can enjoy endless adventures while parents relax and unwind in paradise.

Conclusion: For travelers seeking a timeless retreat in the Caribbean, Round Hill offers a perfect blend of luxury, history, and warm hospitality. Whether you’re lounging by the pool, indulging in delicious cuisine, or exploring the vibrant culture of Jamaica, a stay at Round Hill promises an unforgettable experience that will leave you longing to return again and again.