Some trips just feel different. Maybe it’s the way the air hits you the second you step off the plane, or maybe it’s the fact that this was our first big trip with the baby — but heading to the Big Island of Hawaii in June felt less like a vacation and more like a reset. Thanks to a pile of Hilton points we’d been stockpiling through our Amex, we were about to find out what resort life really looks like.
The Train to Your Room
We booked the Hilton Waikoloa Village, and right away this place made it clear it wasn’t messing around. The resort is massive — sprawling grounds, multiple pools, a lagoon — and to get from the main entrance to your actual room, you have two options: take the train or walk. Yes, a train. A little shuttle that winds through the property and drops you off closer to your building. With a stroller, a baby, and enough luggage to outfit a small army, we took the train every single time... until it broke. The trek from the room to the pool was over a mile. We definitely got our steps in.
Resort Life, Pool Life
Our oldest was in heaven. This kid was made for resort life — lounging, swimming, soaking up every single second of it. The pool was gorgeous, the kind of turquoise water that makes you forget what day it is. But the real showstopper was the lagoon. A real, actual lagoon right on the property where the kids could wade in and swim around. We spent hours there, watching fish and turtles as we snorkeled. The middle one was happy too, though for different reasons — that one’s the explorer. Every time we settled in somewhere, there was another corner of the resort to discover, another path to wander down. The baby, for their part, was perfectly content watching all of it unfold from the shade.
First trip with the baby, a resort with its own train, and a pool the kids refused to leave. This is what points are for.
The Guide That Kept Us Sane
We finally finished the northwest side of the island, and a huge part of that is down to the Shocka travel guide. Seriously — if you’re planning a Big Island trip, get it. It broke down every stretch of road into exactly what’s worth stopping for and what you can skip, which when you’re traveling with a newborn and two kids who have opinions about everything, is everything. The northwest side was stunning in a quieter, less touristy way, and having the guide meant we actually found the good stuff instead of just driving past it. Highly recommend.
← Back to all posts