HAT Blog Maui dispatch: Lahaina

Our Hawaiian Airline flight from Honolulu to Kahului was uneventful, which was enough to make me nearly ecstatic. In the nights before the trip, I had fever dreams of getting seated near some violent anti-mask wingnut of the variety that go instantly viral on social media. Please, no, I begged the Cosmos.

We boarded without incident, people were pleasant (the staff and the passengers), and the cabin was at about 80% capacity. No problem! Bravo, Hawaiian Air. It’s been two years since I last took a flight. I gazed out of my window at Lanai slipping by, and up at the slopes of Haleakala as we approached OGG a little more than 30 minutes after takeoff. Honorable Wife Person is aware of my childlike fascination with airplane window seats, something I don’t think that I will ever lose.

Haleakala Summit, Maui.

Picking up the rental vehicle was a breeze, as was finding and checking into our accommodations located between Kaanapali and Kapalua. We had arrived at supper time. Rather than stopping for a bite, we made a run to the Times Supermarket in Kaanapali to stock up on snacks, adult beverages, and reef-safe sunscreen. We enjoyed cocktails on the oceanfront lanai and decided to head into Lahaina for lunch the next day.

“Yeah, well,” I said. “I guess we kind of have to do Lahaina, right?”

I hadn’t been to Lahaina since the late 1990’s, when my band at the time had a stint at the now long-gone Moose McGillycuddy’s. I’d been to Maui with Honorable Wife Person for some golf at Maui Nui Golf Club and to hang out at Mulligan’s on the Blue while staying in Wailea in 2015. We never made it into Lahaina.

Big boats are big business in Lahaina.

Lahaina hasn’t changed much at all since I was last there. Front Street is still a tourist mecca, with all manner of gift shops, galleries, restaurants, and tour operations lining the storied thoroughfare. It’s been that way for about 150 years, since back when Lahaina was the hub of the whaling industry in the Pacific.

While Honorable Wife Person and the in-laws set out on a shopping mission, I thought I’d stop into Fleetwood’s on Front Street and have a quiet drink at the bar. After almost 30 years in the rock and roll business and being a fan of Mr. Fleetwood and his band’s work forever, I felt it was practically a duty.

Hungry visitors at Papa ‘Aina at The Pioneer Inn.

A bronzed, blond haole lady of about sixty was minding the entrance. She could have come from Central Casting. “Hi!” I smiled cheerfully. “I thought I’d come in for a drink at the bar.”

“Terrific!” she smiled back. “We open at 3pm.” It was 11:30am.

“I guess not then!” I smiled again, somewhat dejected and completely surprised that a restaurant owned by one of the most famous rock musicians in the world, who lives on Maui part-time, would be closed for lunch on a Saturday when Front Street was (nearly) teeming with punters. Welp. Maybe next, time, Mr. Fleetwood!

I settled onto a stool at the bar at Captain Jack’s, which does not require proof of vaccination due to its entirely open-air setup. That made me somewhat uneasy at first. But I’ve been vaccinated, and the restaurant wasn’t busy, I’d reasoned before ordering a double (whiskey and Coke).

The view from Captain Jack’s in Lahaina.

My wife and in-laws joined me 30 minutes later after a successful shopping trip (new bikini, surf swag for the nephews), and we enjoyed a fine lunch. I excused myself and took a stroll down to the Lahaina Harbor and Pioneer Inn.

A colossal dive/tour boat backed into its birth as a twin-engine fishing boat chugged in after it. A small crowd waited for tables in a line outside Papa ‘Aina at The Pioneer Inn. Waves lapped along the seawall along the Lahaina Waterfront. Tourists and locals sat in the shade under Lahaina’s famous banyan tree.

Lahaina’s Front Street waterfront.

We stopped at the Ala Hele Mo’olelo O Lahaina historical site, which is home to centuries of Native Hawaiian history and culture. It’s easy to overlook when window shopping or day-drinking just a couple of blocks down Front Street. We suggest making a point to visit it.

Historic hale in Lahaina.

Lahaina is as I remember it: charming and cheesy. It’s a tourist trap, but Lahaina is honest about it. The actual history of Lahaina speaks for itself and is alone worth the visit. It’s easy to mock the tired Jimmy Buffet “Margaritaville” trope that Lahaina evokes. There are many who bought into it decades ago, and they’re still there. But the real, historic Lahaina is there for anyone willing to seek it out.

Posted by: Jamie Winpenny