Travel Stories: A Remote Jamaica Vacation with a Toddler

I LOVE LOVE this guest post from Laura Siciliano-Rosen. I’ve been to Jamaica a few times and have always gone the resort route. Laura’s trip off the beaten path for a remote Jamaica vacation with a toddler sounds like a wonderful adventure. A few bumps here and there, but those happen even when you’re headed straight to a resort! I’m delighted she’s sharing her trip to Port Antonio with us.

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Remote Jamaica Vacation with a Toddler

Some trips with a toddler are easier than others. After several successful jaunts—Denmark, Sweden, Mexico, Louisville, Charleston—with our little guy, my husband, Scott, and I were reasonably confident about a road trip along Jamaica’s north shore.

Our sights were on beautiful, off-the-beaten-path Port Antonio, where the lush coast meets the Blue Mountains (a region rumored to have some of the country’s best food, always an essential for us).

A Babymoon with a Toddler

I was five-months pregnant and eager to escape a freezing New York winter for a beachy “babymoon.” Driving to the jungle, swimming all day, eating in local Rasta shacks—what could go wrong?

We learned that Port Antonio isn’t the easiest sort of trip. To do it justice, you require an exploratory spirit and a little bit of research. The mellow, remote region (often called the forgotten “real Jamaica”) doesn’t lay it all out for travelers. You navigate the dusty city and its rural, startlingly gorgeous outskirts yourself to find the gems.

It pays to see what’s around the corner here: to push on to the next beach, to continue down that vine-draped road, to wander into a few shacks and see what’s bubbling beneath the pot lids. This was generally our style of travel anyway. We were determined to train our son (then 22-months) in its many delights.

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Books at bedtime in Montego Bay | photo: Laura Siciliano-Rosen

Day 1: Montego Bay

We flew into Montego Bay first. Got ourselves a rental car, installed the car seat we’d brought with us—our first time checking it at baggage—picked up some beef patties from the stand outside the airport (priorities!) Then we drove the 10 minutes to our hotel for the night, the Gloucestershire.

For past trips we’ve rented car seats, but decided to bring our own for this trip since we knew we’d be doing lots of driving. We had a hard time choosing accommodations here, since we generally travel with a two-bedroom rule: one for us, one for him. Everyone is happier this way. But the hotel we wanted to book, which offered two-bedroom suites, didn’t provide cribs, and that’s another travel rule for us: no lugging around pack-and-plays.

Needless to say, our son snoozed in the closet that night at the Gloucestershire (with the door open, of course!)

None of us slept particularly well.

On the plus side, the hotel had an excellent Jamaican breakfast buffet, and he loved his first taste of callaloo and mackerel rundown.

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Winding Road, Port Antonio | photo: Laura Siciliano-Rosen

Day 2: Montego Bay –> Port Antonio

After a few hours on Doctors Cave Beach (across the street from our hotel) we had to hit the road. According to Google Maps, the drive was about three hours. But here in Montego Bay, people were very surprised to hear where we planned to drive. “Port Antonio? Today?” one man said incredulously, glancing at his watch. Why, how long is the drive? we asked. “I don’t know, four, five, six hours, maybe,” he said.

You’d think we’d planned to drive to the far side of the Earth that afternoon.

Still Driving to Port Antonio

But he wasn’t the first to question us. Along the drive, the first two hours of which was on a reasonably fast highway, we stopped for peanut porridge, jerk chicken, more beef patties. And everyone, no matter where we were, estimated we still had about three hours of driving ahead of us. This includes the two speed-gun-happy local cops who pulled us over.

We laughed about it. But as the day waned, we grew increasingly nervous. Our son had long ago woken from his nap. He was getting antsy, and it would be dark soon.

Where was this place?

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Worth the effort: Blue Lagoon, Jamaica | photo: Laura Siciliano-Rosen

Driving in Jamaica — on Jamaica Time

Ultimately it took about five hours altogether to drive from Montego Bay to Port Antonio. The last two hours were slow and winding, through increasingly lovely, lush coastal country.

It was late, we were hungry, and we had no idea where to park. Our home here was the Moon San Villa, perched steps from the pretty Blue Lagoon (yes, that one). It was set between two narrow, tree-lined roads, no parking lot in sight.

Day 2… Continued

And once parking was resolved, and we lugged all our stuff into our small, two-room suite, there was a second pressing issue: food.

Our son’s bedtime was approaching, and we all needed to eat something substantial. We forgot that our hotel doesn’t serve dinner without advance notice. In fact, several restaurants in the region operate this way. You reserve your meal the day before so groceries can be purchased. Nothing was walkable. Once we accepted we’d have to get back in the car, we turned to the staff for help. What were our options?

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Boston Jerk Center, Jamaica | photo: Laura Siciliano-Rosen

Dinner #1 in Port Antonio

We settled for burgers and fries on a nearby crescent-shaped beach, Frenchman’s Cove. We raced over with our cranky boy just before the deserted restaurant closed. Our meal was so-so and not particularly Jamaican. However, we had the darkening sands and rolling waves to remind us where we were. Basic needs met, we retired for the night, wondering aloud (as we often do in moments of toddler-travel exhaustion) if perhaps an all-inclusive resort rather than a remote Jamaica vacation is the more relaxing way to go next time.

Gratefully, things improved over the next few days. We got the hang of Port Antonio.

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Cruising the Rasta Shacks | photo: Laura Siciliano-Rosen

Day #3: Worth the Work

We had to work a little to uncover the area’s charms, but they were plentiful. To reach the beautiful public beach Winnifred’s, we made a few wrong turns. And then we realized we had to ease our car down a long, steep, bumpy dirt road.

But then we spent the better part of a day there on near-empty sands sipping fresh juices and cold Red Stripes, swimming with our son—who took a nice long nap on his dad in the Ergo carrier—and taking shelter from a passing storm in a Rasta shack with excellent curried lobster.

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Waiting for the rain to stop | photo: Laura Siciliano-Rosen

Happy Accidental Finds

The laid-back enclave of Long Bay, a short drive further east, we visited by accident, when our son fell asleep in the car and we just kept driving. There, we discovered another picturesque beach and a slew of tempting roadside shacks.

When he finally awoke, we wandered into the welcoming musical confines of a restaurant called Fisherman’s Park, lingering over delicious conch soup and baked chicken with a content and well-rested kid.

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Morning hike, Port Antonio | photo: Laura Siciliano-Rosen

Toddlers Will Be Toddlers

Mornings were tough. Before we even left home, our son began a waking-and-screaming-at-5am phase that ultimately lasted a good six weeks. The hotel didn’t serve breakfast until 9. Unfortunately the narrow streets below, and lack of beach in the immediate area, meant we couldn’t hang out outdoors either. We had a lot of time to kill.

What got us through: cereal bars and toy cars brought from home, locally purchased fruits and snacks (albeit the latter had a bit more sugar in them than I’d like), the kitchen’s fridge (where we kept his milk), and (when we got desperate) our iPad.

Breakfasts in Port Antonio

Around 7:30-8, the kitchen staff and the few other guests there were up and about, so we could venture outside to our long shared terrace and breathe a sigh of relief—over lots of local Blue Mountain coffee.

And then, the morning’s true reward revealed itself. We discovered we could have the clear, tranquil Blue Lagoon completely to ourselves if we timed our visits just right. After breakfast, while there was still morning sun on it but before the day-trippers showed up turned out to be our magic hour.

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Moon San Villa mornings | photo: Laura Siciliano-Rosen

Longer Is Better

In retrospect, we would have extended our five-day trip. The driving to and from Montego Bay equaled two long travel days, and the route through the mountains from Kingston is said to be harrowing. And we should have booked a two-bedroom private villa, like this one (it wasn’t available during our dates), so we had more space to play in the mornings.

Still, it was nice to have a hot Jamaican breakfast prepared for us every morning at the Moon San Villa. And the staff offered another benefit: free babysitting. We were happy to take advantage of that for two adult dinners out.

Final Thoughts on Our Remote Jamaica Vacation with a Toddler…

It wasn’t flawless. And there were plenty of tantrums. But as with any sort of travel, the low points are quick to fade. They leave behind great memories that only sustain and strengthen our growing little family.

Aside from reflecting on how we’d do this sort of trip next time, we learned our son loves ackee and saltfish, swimming in cool clear lagoons, and dancing to reggae.


Who knew?

About the author: Laura Siciliano-Rosen is the co-founder of food-travel website Eat Your World, an original guide to regional foods and drinks from different cities around the globe. She lives with her husband and two small boys in Queens, New York.

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4 Responses to Travel Stories: A Remote Jamaica Vacation with a Toddler

  1. Wonderful pics. Jamaica looks great. What a great opportunity to discover a place through the eyes of a kid!

  2. angel at #

    its difficult to travel with babies but you done with it and the baby looks soo cute and thanks for sharing the post.

  3. Nice post.. how u managed to travel with your kids.. its really nice

  4. it looks like a really fun trip and the baby definitely had some good time. I consider people who travel with small children to be extremely courageous, so great work you guys!

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