ILLUSTRATION BY Alice Des

One Love

An Oceanfront Villa and Three Generations in Jamaica.

March/April 2026 - Virtuoso, The Magazine

AS EVERY TRAVELER knows, milestone birthdays are the perfect excuse for milestone trips. But when my husband was planning for his 70th and our sons asked, “What are we doing for Dad’s birthday?” we realized our family had morphed into something very different from the one that had trekked the Andes for my 50th and the Dolomites for my 55th. We were now multigenerational with two grandsons: one a toddler, the other barely 4 months old. We needed a new kind of trip. But what? To make matters even more complicated, our nuclear family had split off to New York, London, and a small town in Idaho.

I consulted friends who’d already mastered multigen travel with little ones in tow. Their advice: Rent a villa in a location that’s easy for everyone to fly to – and to make the most of your time together, look for something fully staffed. Depending on the destination, they said, it’s not always as pricey as it sounds.

Encouraged, my husband and I focused on the Caribbean – warm, beautiful, entertaining for all, and accessible via direct flights from New York and London for those flying with babies – and chose Jamaica. That’s when the real fun began.

We discovered The Tryall Club on Montego Bay’s northwest shore – home to 92 secluded, privately owned, fully staffed villas spread over 2,200 lush acres of a former sugar and rum plantation. The resort offered enough lowkey activities for everyone: a pristine sandy beach, a beach club with a pool, a championship 18-hole golf course, tennis, pickleball, a kids’ club, and a holistic spa with yoga classes.

Because it was his birthday, my husband got to choose the house. “I’m only turning 70 once. Let’s rent this one,” he said, pointing to a stunning oceanfront villa with a pool and a huge lawn rolling to the sea. The house was a splurge but looked just like him: a little salty, elegant and relaxed, but fun. We plunked down a deposit, booked our flights, and hoped for the best.

MY HUSBAND’S BIRTHDAY falls in October, but we decided to celebrate the following February to avoid hurricane season. We didn’t want to risk things.

This past October, Hurricane Melissa, one of the most powerful Atlantic storms on record, made landfall in Jamaica. It was the most intense storm to ever hit the island. Having loved our week at Tryall last winter, where we were welcomed by villa staff so warm they felt more like family, we watched the storm’s path with alarm as it pummeled the island’s western side and exited over Montego Bay, destroying homes, schools, and roads, and displacing an estimated 30,000 families, cutting off access to power and clean water.

“Hurricane Melissa tested us in unforgettable ways,” said Angella Bennett, a regional director at the Jamaica Tourist Board. “But we are resilient. We are resourceful.”

According to Bennett, the challenges have underscored the Jamaican people’s courage and strength, and the best way to give back is to come back.

Tryall’s managing director, Kenton Jones, agreed. “The whole country depends on tourism – this year, even more,” he said, when we spoke after the storm. Even though the island’s main tourist areas are recovering quickly, he noted that the interior is rural and hard to reach, and will take a long time to recover. Despite all these trials, however, people are rebuilding and life is returning to normal.

The house was a splurge but looked just like my husband: a little salty, elegant and relaxed, but fun.

WHEN FRIENDS ASK what made Jamaica so special, different things come to mind: our breezy villa overlooking the bright turquoise sea; the simplicity of relaxed mornings on an open-air terrace, grandkids still in their pj’s; the house’s three golf carts, which made it easy for everyone to zip around, do their own thing, and find one another. Alfresco breakfasts at a big round table with a lazy Susan offering homemade banana bread and fresh tropical fruit, and our butler casually asking each of us, “How would you like your eggs this morning?”

I loved watching for lizards and f loating in the pool with my toddler grandson, saying “Yes!” every time he wanted to go swimming (about six times a day). My husband and sons loved the Ralph Plummer-designed golf course and the thrill of playing in Jamaica surrounded by such natural beauty. One son and I enjoyed the spa’s uplifting yoga classes, led by a woman with dreadlocks who seemed about seven feet tall, and my daughter- in-law and I had a blast driving our golf cart over the hills and through the tunnels, picking out favorite villas for our next visit.

For all of us, though, it was the staff’s low-key charm that left the most lasting impression. One night they set a table on the lawn overlooking the sea with tiny lights and masses of bright-pink bougainvillea for a delicious barbecue. For our thirtysomething son, also celebrating a birthday that week, they bought live spiny lobsters from a local fisherman and baked James his favorite cake: chocolate with coconut frosting.

And my husband’s milestone birthday? He loved the Jamaican vibe and felt totally spoiled and celebrated. When here turned to our room one day, he found a T-shirt he’d accidentally left on the floor perfectly laundered, pressed, and folded. We all had to smile.

For a man who loves reggae and rum – and still does his own laundry – this was a milestone indeed.

VIRTUOSO, THE MAGAZINE

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By Kim Brown Seely.  All rights reserved.