Jamaica

The Trip Before Everything Changed

By Thanksgiving 2023, I was a little more than six months pregnant with Avery, Preston had just turned two and our family was already beginning to imagine how travel would look once there were four of us. Before that next chapter began, we wanted one warm, uncomplicated pause together.

Jamaica came together for practical and personal reasons. The flights were more reasonably priced than the alternatives we were considering, Kyle had wanted to visit and the timing gave us a chance to celebrate his birthday as well as take a babymoon. Just as importantly, Montego Bay offered the kind of trip we needed: a relatively easy travel day and no expectation that we would wake up each morning ready to cover a long itinerary.

We knew before we left that this would be our final vacation as a family of three.

We were already planning the parental-leave trip we hoped to take with both boys, so the change ahead did not feel abstract. We understood that Preston would never again occupy these travel moments in quite the same way. We could take individual trips with each child later, but this particular season — Mom, Dad and Preston moving through the world together — was ending.

That awareness gave even the simplest moments more weight. We did not spend the trip chasing attractions. We ate breakfast outside, alternated between the beach and the pool, and let the day unfold without a schedule. At two, Preston was happiest jumping into the water and splashing with the pool toys. At more than six months pregnant, I was happiest having nowhere else we needed to go.

Our Stay at a Glance

Four nights in Montego Bay over Thanksgiving 2023 — part birthday, part babymoon, and a deliberate pause before our family grew to four. We based in a private family home, used a car service for every transfer, and built the days around only two choices: the beach or the pool.

Choosing Ease from the Beginning

We flew from Columbus to Atlanta and then continued to Montego Bay. The home's car service met us at the airport and handled the drive to the property. We had not fully considered before arriving that drivers in Jamaica use the left side of the road, so having transportation arranged immediately felt especially helpful.

We did not rent a car. The same service remained available for the entire stay, taking us to the beaches and returning us to the airport. Because this trip was built around rest rather than independent exploration, we never felt that we were missing the freedom of having our own vehicle.

A Home Designed for Family Life

We stayed in a private home in Montego Bay connected to a friend's family. It was a lived-in residence rather than a property designed for tourists, and that difference shaped the entire stay. The atmosphere felt comfortable, personal and genuinely homey.

Each morning, the home's chef prepared breakfast and set it out on the terrace. We could look toward the ocean, watch people on the nearby golf course and begin the day slowly over fresh fruit and tea. There was no need to locate a restaurant, rush through a meal or decide where everyone needed to be next.

Beach, Pool, Repeat

After breakfast, we usually chose either the beach or the pool. If we visited a beach in the morning, we returned to the pool in the afternoon; if we began at the pool, we might head to the sand later. That was the itinerary.

The slower pace was not an accidental byproduct of having little planned. It was the right design for this particular trip. I was becoming increasingly uncomfortable and tired as the pregnancy progressed, and Kyle handled most of the chasing after Preston around the property. We stayed close to home and allowed rest to be part of the experience rather than something that interrupted it.

Pool Days with Preston

The image that remains most clearly is Preston splashing in the pool. He enjoyed the beach, especially digging and playing in the sand, but the pool made him happiest. He jumped in, splashed, climbed onto the loungers and played with the pool toys available at the house.

There was nothing elaborate about those afternoons, which may be why they matter so much now.

We were not watching the time or preparing to move to the next stop. We were simply watching our newly two-year-old delight in the water during the final trip when he had both parents — and the shape of our travel days — to himself.

Doctor's Cave Beach

We visited two beaches during the stay, but Doctor's Cave Beach is the one we returned to and remember most clearly. During our visits, we had room to spread out, found chairs easily and never felt crowded.

We walked along the shoreline, stepped into the water, played in the waves and let Preston dig in the sand. The beach did not need to supply a full day of entertainment. It gave us a beautiful place to slow down for a few hours before returning to the pool he loved even more.

Most Meals at Home

The chef at the home prepared most of our meals. We ate jerk chicken, rice and vegetables, rice and peas, fried plantains, fresh fruit and a curry- or stew-style dish. Kyle also tried ackee and saltfish. In the mornings, tea became one of the small rituals we looked forward to. We occasionally ate lunch or snacks at the beach, but restaurant planning was not part of this trip. Having meals prepared at home removed another decision from the day and made it easier for me to rest.

The Picky-Toddler Reality

Preston was in a picky-eating phase. He relied on oatmeal and fruit at breakfast and ate plenty of grilled cheese and peanut-butter-and-jelly sandwiches. We did not need him to become an adventurous eater for the trip to count as a success. He was fed, he was happy and that was what ultimately mattered.

A Quiet Birthday Toast

We had already celebrated Kyle's birthday with cake several weeks earlier, so Jamaica did not include another formal birthday event. We raised a glass — non-alcoholic for me — to him, to the trip and to having this time together as a family.

What Helped Our Family

• A four-night stay with no pressure to turn each day into an excursion.
• A private pool that gave Preston room to play without leaving the property.
• Prepared meals and breakfast on the terrace.
• A car service for every airport transfer and beach outing.
• Sharing the physical work differently while I was tired and uncomfortable.
• Letting a picky toddler eat familiar food without turning meals into a struggle.

A Difficult Departure

The hardest part of the trip came at the airport on our return home. There were multiple rounds of screening, the terminal felt very hot and I was already carrying the fatigue and discomfort of being more than six months pregnant.

Before boarding, I was selected for an additional check. Because I had touched certain bags, those bags also had to be opened, examined and repacked. From what we could tell, several other passengers were being selected as well, but we did not receive a clear explanation of how the selections were made. Kyle and Preston could not remain with me during the process, which meant Kyle could not help repack the luggage. Completing that task alone, immediately before boarding, with limited air conditioning and very little energy left was an especially difficult end to the trip.

That experience has made me more hesitant about returning than I otherwise might have been. It does not erase the quiet days we enjoyed, and I expect we will give Jamaica another chance. It remains an honest part of how this particular trip felt.

Four Nights Were Enough

For the trip we intended to take, four nights was the right amount of time. We would repeat the empty schedule, the private pool, the prepared transportation and the freedom to decide between only two things: beach or pool.

Doing less was not a compromise. It was what allowed the trip to work.

We would not add excursions simply to make the itinerary appear more substantial. At that point in my pregnancy, and at that point in our life as a family, doing less was exactly right.

Would We Return?

In time.

Jamaica gave our family exactly what we needed in that season — an unhurried Caribbean pause between one chapter and the next. The departure was harder than the rest of the trip, and it has shaped how quickly we plan to return. But the quiet days by the pool, the terrace breakfasts and Preston's laughter in the water are the pieces we carry with us.