How to Nail a Long Layover

When I’m booking a flight, I don’t search by shortest duration, I sort by longest. My favorite flights are those that include one or more really long layovers during the day in an interesting location.

Earlier today I hiked up Diamondhead, ate a Hawaiian burger, waded into the ocean at Waikiki, and visited the Honolulu Art Museum. But I’m not on vacation in Hawaii, I’m on a six hour layover on my way to Tokyo.

My favorite way to do a long layover is to have a big list of things I want to do, and then hit them at whatever pace I feel like. I want to avoid wasted time at all cost, but not rush myself.

We rented a car in Hawaii, which is almost always worth it in these situations. For $40, we were able to avoid any sort of waiting around or having to conform to time tables. We did things like lunch and the hike, where we’d have only limited control over our schedules, early so that we wouldn’t end up in a situation where we haven’t got the check yet and we have to hustle back to the airport.

The museum was really fantastic. It had some of the best Japanese woodblock prints I’ve ever seen, the best Roy Lichtenstein I’ve ever seen, and a solid collection of Goryeo dynasty pottery. My friend Brian is really into sculpting (he created Oculus Medium), so he was excited about the great Rodin exhibit they had. We ended up spending a little more time there than expected, but when an activity is a 10/10 there’s no benefit to rushing yourself.

We were hoping to have time to swim or bodysurf at Waikiki, but our time spent at the museum only left us with about twenty minutes there. We still felt great about it, though, because a layover is all bonus time. We ended up doing a nice sampler of Honolulu, and we can do more next time we’re here.

Sometimes you’ll have a shorter layover, like just two or three hours. I really like having those in certain European cities like Amsterdam where it’s quick and easy to get into the city. In those cases I’ll choose just one thing to do that has a variable length, like visiting a museum, and focus on that. Once in Amsterdam I hustled onto a train to head to the Delft just to see one Vermeer painting. Another time my friend Leo and I played a round of pitch-and-putt golf in Vancouver on a four-hour layover.

Breaking up a trip with a great layover makes it feel like two shorter trips. I feel like I’m on a nice short eight hour direct flight to Tokyo, not a thirteen-hour connecting flight. And my whole trip to Hawaii cost around $50. Not bad!

I really love finding things that are undervalued because other people don’t like them, and then figuring out a way to turn them into something that adds value for me. A nice long layover is perfect. Sometimes I’ll even take a long layover just to hang out in a good airport lounge. I love the Centurion Lounge in Dallas, so I’d prefer a connecting flight with a few hours there than a direct flight.


Photo is the view from the top of Diamondhead.

Sorry about the extremely late post this week– got caught up with Christmas stuff.

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