Maui Hawaii, USA

We’ve done beaches all over the world: the Caymans, the Bahamas, more of Mexico than we can count, the Virgin Islands. Hawaii is different from all of it. The landscape, the plants, the sea life, the whole thing feels like another world, and this trip was 100% worth going. Maui is really two trips, and we’d do both again. Start quiet in Hana: the black-sand beach at Waiʻānapanapa (book the timed entry), the slow pace, a resort tucked at the very end of the road. Then move to Kā’anapali for the back half: Black Rock off the beach, a pool the girls won’t leave, and big west-side sunsets.

Here’s the one thing we’d tell you before anything else: drive the Road to Hana slowly. Our first day we tried to push straight through to the far end, and the kids fell apart somewhere in the switchbacks: carsick, done, mutinous. On the way back we stopped every ten or fifteen minutes, let them out to poke around each waterfall, and it turned into the best day of the trip. Same road, completely different day. Split it: do some stops on the way out and save the rest for the way back, so nobody’s trapped in a car seat for three hours straight.

20.7984° N, 156.3319° W

One logistics move that made the whole day easier: download the offline Google map for Maui before you leave the hotel, because you lose service for most of the drive. Look up each stop, save it, and string them into one multi-stop route the night before. There’s one gas station out this way, in Paia, so fuel up before you go.

Our favorite stops, roughly in the order we loved them:

• Twin Falls (Mile Marker 2): the easiest first waterfall, a short farm walk to pools you can actually swim in. $10 to park.
• Garden of Eden Arboretum: paid, and worth it. Big views, and peacocks wandering the lawns.
• Keʻanae Peninsula: black lava coastline and hard ocean air; you feel the whole island out there.
• Aunt Sandy’s banana bread: warm, handed out the window, worth the stop if the line’s moving.
• Puaʻa Kaʻa State Wayside: a little waterfall the kids can actually get into. The kid-friendly one.
• Coconut Glen’s: coconut ice cream in the jungle; a two-minute stop that buys you twenty of goodwill.
• Hana Farms Roadside Grill: wood-fired pizza and a yard to sit in. One of our favorite spots on the whole island, no reservations.
• Waiʻānapanapa (the black-sand beach): make the reservation, thirty days out. This is the one people picture when they picture the drive.
• Hamoa Beach: past Hana town, quiet and easy, one of our favorite beaches anywhere.

We skipped the Pipiwai Trail. The way our day routed, it added too much, and we’d rather have spent the time stopping along the water. No regrets; there’s more out here than you can fit in one drive.

Then there’s where you stay, because the room you come back to is half the trip.

The Hana-Maui Resort, the Hyatt at the end of the road, is the one we’d go back for. We booked it for 70,000 points transferred from Chase to Hyatt, a genuinely great deal for what you get, and they upgraded us to one of the bungalows. Great pool, kind people, the black-sand beach fifteen minutes away. We wish we’d stayed longer.

The Sheraton at Kā’anapali was fine, and honestly just fine. We got it free on Marriott credits plus points and bumped up to a suite on Platinum status, and Black Rock is right off the sand. But it’s tourist land: busy, a little cheesy, too many people. Great for what it was; we didn’t love it.

On our last day we splurged on the Marriott Wailea Beach Resort, and that was 100x more our vibe. The main pool is great and the kids’ slide pool is better; the girls would’ve lived in it. We wish we’d booked it for more than a day. Worth knowing about if the pool is the point of the trip.

While we’re being honest: we did the luau. It was super cheesy and really expensive. We’re glad we did it once, the girls had fun, and we would never do it again.

One small tip that made the beach days easier: a company called The Snorkel Store rents beach chairs and, better than that, posts a daily read on the surf and which beaches are actually good that morning. That’s the report you want before you drive twenty minutes to a windy beach.

For snorkeling, the rule is simple: only when it’s glassy. Black Rock off the Sheraton side is easy on a calm morning, but don’t round the tip with kids; the current there grabs. When the west side kicks up, South Maui (Maluaka, Ulua) usually stays calm.

And get the girls a lava flow served in a pineapple at least once. About fifty bucks for a slushie with an umbrella, and one of the things they still bring up.