Out of the countless stories written about this legendary property, the common thread remains, its timeless elegance. Round Hill, those two little words have such resonance, globally. It can be quite intimidating to write about legends. Since 1953, the collection of luxury villas and exquisitely appointed ocean-view rooms and suites, has welcomed travelers of a certain caliber. Celebrity guests roam the property undisturbed from diving into their best vacation at this resort. Guests who don’t happen to be movie stars, top athletes, royalty, television personalities, designers, your above average millionaires, or what have you, do quite well fitting right in at the property. It could be that the staff has seen it all and is so well trained and well versed in hospitality but no matter what Walk of Life, you are going to be well taken care of here. I’ve been coming to this Resort for over 22 years and with all the upgrades to the amenities and outfitting the property with things like refillable water bottles in each suite and water filling stations throughout the property, none of these modern-day necessities are garish or glaring. The sensibility of Round Hill remains the same. Seeing friendly faces and being welcomed home is a remarkable experience. Upon checking in this time someone at the front desk said, ”Everything has changed.” For the life of me I couldn’t understand why they would say that. I like the old Round Hill. I like the classical elements that took me back in time and captured an era that appeared, in black and white images, to be simpler, and swankier than anything encountered these days. Inside I silently wept. The large circular mahogany entry table was the same. The polished wood reception desk looked unchanged, and when I was handed the key to my suite, the brass oval keychain with the pineapple logo was still the very same. Surely, she couldn’t mean the refresh on the signature green and white striped awnings. Fabric always needs to be updated, so, I would not say the crisp new awnings were not a “change”, but rather the sign of a well taken care of resort.

As we walked down the black and white checkered steps, our view of the beach opened up. The call of the sea gently lapping at the crescent-shaped beach was strong, but in keeping with the tradition of not swimming in the clothes we stepped off the plane in, we hustled to our oceanfront balcony room and changed. Along the short path to our room we passed the resident artisan Richard Straw Boss, a renowned local artisan who weaves some of the island’s finest baskets and handbags right on the lawn at Round Hill.⁠ He’s another staple with a warm, “Welcome back!” and a wave, we feel even more at home. The simple acts of genuine warmth and incomparable hospitality make a vacation at Round Hill unmistakable and unparalleled.

We used to take Cottage 18 on this property for many years and the ladies who were the staff of that villa had been working there for decades. The former director of sales and marketing had also worked there for decades and knew us by name. These stalwarts are the gatekeepers to the most laid-back luxurious vacation one may ever take. Josef Forstmayr, the managing director, is beyond comparison. You can find him strolling the property, with a keen eye on the grounds and the guests, ensuring every detail is as it should be, and the guest experience is on point. Matter of fact, he had inspected our room just before arrival and left a handwritten note welcoming us back. We actually saw him post the room inspection on Instagram, not knowing it was ours until we arrived. Talk about melding the classic standard of superior hospitality with the new technology. Round Hill will never cease to amaze on every level.

Talk about telling stories…the Ralph Lauren Bar, named after the designer who also happens to be one of the notable residents of Round Hill, has more stories to tell than any other nook on the property. Slip into a cozy corner for a classic cocktail while the pianist tickles the ivories and gaze at the black and white photographs in their original frames and you’re immediately drawn into an era of swank and style. The swimming costumes, grinning faces, and the recognisable appearance of relaxed luxury jumps out at you. After reemerging from the captivated grasp of the past, you soon realize that you are indeed making the same indelible images and memories for future generations. Even if your images never hang on these hallowed walls, memories made at Round Hill become instant classics. The resort is crawling with nostalgia. The beach bar, built around a thriving almond tree, has been there since the start and only gets better with age. Stewart tends to the bar as though it were a child of his and takes just as good a care of those who visit him for a libation or two. The rafts anchored just offshore are a great sunbathing and people watching spot. Here, there is not the type of people watching one might do in a busy city or in Hollywood on the hunt for stars. It’s the sort where you make connections. The rafts are a sort of gathering spot to strike up conversation while chilling in the sea. I do not believe that has changed one bit since 1953. Lifelong friendships have been made on this golden sand beach. We can personally attest to that.

The spa holds the same warmth and charm as the rest of the resort. The Welcome Wharf, home to the spa is an 18th-century home, meticulously renovated on over ten acres of lawn that leads to an intimate private beach. This beach is one of our favorites for collecting sea glass, a secret shared with only a few until now. Setting foot onto this adults-only area of the property is transformative. This, before ever having a treatment. We love grounding ourselves by kicking off our sandals and stepping on to the zoysia grass, dotted with fallen almonds from the shade trees strewn across the lawn. This coupled with the gentle sea breeze and the sound of rolling waves gently tumbling the rocks on this side of the resort are enough to make us melt into the next level of relaxation. We can’t do that just yet, as treatments await. Although we elected to have our services in air-conditioned rooms, the tranquility of our previous outdoor experience would not be disturbed. Our new emersion was waiting from the moment we stepped into the treatment rooms complemented with a cold glass of champagne and lovely chocolates. Can we say decadent indulgent relaxation? We absolutely can. From the 18th century to the 21st century, some things never change. This former residence was built purposefully on this piece of land for all the attributes it has to offer today. A calming, grounding, station by the sea. We are thankful for that and for its enduring existence.

As a matter of fact, we are thankful for all of the elements that make up this classic. Come once and Round Hill will never leave your soul. Come back again and it will become a part of your life and lifestyle. Timeless elegance never goes out of style.


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