On the Road — and the Beaches — in Maui with Friends

The Hawaiian island’s tropical embrace offers a memorable vacation in paradise.

“Did you hear that, too?”

Yanking the snorkel out of my mouth, I turn, nodding yes, to my friend Peter. He’s studying the open water behind us just off Ka’anapali Beach, a beautiful stretch of sand snuggled between the West Maui Mountains and the marine-protected waters of the Au'au Channel.

For the last half-hour, we’ve been enjoying the underwater show, swimming among vibrant yellow tang and schools of big-eyed Hawaiian flagtails. Just after rounding the point, we hear it. First a faint clicking sound, then whistling. “Are those whales?” I ask. Peter starts to respond, but his words trail off as he quickly dives. I follow him.

Peter and I grew up together. When our shared hoop dreams ended in high school, we turned to rafting, canoeing and backpacking together. After college, he got married and found his calling as a lawyer. I moved to Alaska and took more time finding mine. Through the years, our frequent adventures turned into exchanged texts promising, “I’ll check my schedule.” It happens. But Peter was my best man when my bride Hailima and I said, “I do” in Alaska in 2019. At the reception, when Peter proposed a trip to Maui with our wives, all of us were enthusiastic.

The deeper Peter and I dive, the clearer the whales’ calls become. For the next five minutes, we float beneath the water, listening in on migrating humpbacks socializing during their journey through the channel. Later, we excitedly share our surreal encounter with Hailima and Aubrey as we all sit around the hotel pool with Mai Tais in hand, toasting our amazing first day on the island.

Maui’s charm is well known. Three million people visited in 2019, enjoying outdoor fun, epic sunsets and the island’s astonishing natural beauty. We’re in West Maui during high season — mid-December to mid-April — and each day I expect the island to feel busy, more up-tempo. But instead, its paradisiacal embrace is refreshingly low key and relaxing. Back home, our days are always hectic, so we all agree it’s nice to chill here, laughing together and enjoying good times with no set agenda.

After lunch, we’re ready to tackle the legendary road that leads to Hana, an isolated community on the eastern end of the island. A 64-mile-long stretch of Routes 36 and 360 that connects Kahului to the town of about 1,200, the Hana Highway boasts 600-plus turns that twist you, squeeze you and continually test both your driving skills and road etiquette.

“You never know what’s around the corner,” Aubrey says as the drive takes us over one-lane bridges, through lush rainforest and along steep cliffs with breathtaking ocean vistas. With our late start, we only make it to Halfway to Hana, a roadside snack shop that sells sandwiches, beef jerky and homemade banana bread. We buy the bread, put Bob Marley’s music on the radio and head back to our hotel, chasing a majestically setting sun.