Repeat Travel

I Can’t Shake Hawaii: An Ode to Returning to Places You’ve Been Before

Debra Klein on the beauty of finding yourself by returning to the same spot over and over again.

Images Etc Ltd/Getty

My cheek hovers centimeters from the triple thick pane of germs and grime separating me from the object of my affection; my contorted backward glance suggests I’m trying to read something affixed to my upper lip. I take a last longing glimpse, before facing front and reality: the desolate in-between before I see my beloved Hawaii again. As the plane rises onto the invisible highway and the watery horizon and milky sky meet, I’m lost in thought, trying, as always, to figure out a way to make this arrangement we have more permanent.

Such destination devotion once repulsed me. Retracing steps violates the sacred covenant of travel: thou shalt romance “the new.” My travel mission statement was always more George Clooney than Swallows of Capistrano. Hit it and quit it. No returns. Gulliver never took a Mulligan, that’s the rule.

How can we get psyched to visit someplace we’ve already visited? Nothing ventured, nothing gained, right? We’re not having a fresh experience, learning a new culture, seeing sites or people we’ve never laid eyes on before…or are we? If the scenery is the same on the outside—if our thoughts aren’t overrun with running all over—maybe then we’re able to journey within.

In my late twenties, I dreamed of Thailand, thought I’d move to artsy Bali, but started visiting antiseptic Singapore, instead. It was convenient. After slogging through the muddy, buggy cross-island trek on Malaysia’s Tioman Island, I just wanted something easy, something I didn’t have to think about. I collapsed on Singapore’s gleaming doorstep for a revitalizing clean-sheets-and-sterile-street-food weekend. Another year, another fling; I breezed back to the country after separate punishing camel-and-elephant-back excursions in Rajasthan and Sri Lanka; two comfy spa days helped me forget my misery.

Being stupid for Singapore was embarrassing. I worried about how mani-pedi slumber parties with the Paris Hilton of Peninsular Asia was chipping away at my outdoorsy trail cred. Couldn’t I hack “real” Asia? Was I some sort of princess? Should I relinquish my passport and book permanent passage on an infantilizing escorted “adventure” to the Mall of America next?

It wasn’t until I made a special twenty-four hour journey just to see Singapore that I realized this was more than infatuation. What kept reeling me in?

Singapore’s pulse felt democratic; everyone—young and old, rich and poor—was doing the exact same thing. Swept like one corpuscle among thousands clogging the city-state’s underground, air-conditioned retail blood vessels, I realized my pathology made me tap this particular travel vein.

The youngest child by more than half a decade, I’d always felt better times had bypassed me — “my” family’s Dirty Dancing Catskill summer reveries were alive with drama, dance, humor and adventure. They were missing only one thing: me. In Singapore, I was a Brady at last, shuffling alongside an endless stream of siblings.

Older and wiser and lured by post-9/11 airfare specials, I ended up in a decade-long threesome, adding Australia’s “Sunshine Coast,” and New Zealand, the “Land of the Long White Cloud,” to balance the antipodean poles of my personality.

Each December, I flew sixteen hours to Noosa—the Ocean Drive of Oz—a tony shopping and dining enclave where I rarely toed the (in my mind) shark infested surf, but swam in my own thoughts instead. I was a traveling hermit, holed up in a hotel by-the-sea. By the time I reached New Zealand, I was eager for chatter and struck up conversations everywhere, growing extremely curious about agrarian minutiae, and really, really fascinated by the way people raised llamas to knit sweaters and capes. I bought these, and linens and house wares, stockpiling people and things while disgorging inner thoughts at a rapid pace.

Annually, before my arrival, I’d make grand plans to hike a Great Walk in New Zealand, or drive the round-the-island Tasmanian trek, yet I was happiest clipping my own wings. Why fly so far just to nest?

Catching my reflection sipping Sauvignon Blanc and fingering the stitching on my new duvet in my glass walled Kiwi bach (beach home), I realized I was most titillated in this ménage a trois by the role play. Here I could live in a way I could never afford to at home, from uncluttered surroundings to uncomplicated relationships. My Down Under over-the-top lifestyle compensated for my “real” life asceticism in the United States.

Get The Beast In Your Inbox!

Daily Digest

Start and finish your day with the top stories from The Daily Beast.

Cheat Sheet

A speedy, smart summary of all the news you need to know (and nothing you don't).

By clicking “Subscribe,” you agree to have read the Terms of Use and Privacy Policy
Thank You!
You are now subscribed to the Daily Digest and Cheat Sheet. We will not share your email with anyone for any reason.

Maybe we board planes, boats or cars not only to gather experiences, but also to create the person we want to be. For a week, we’re Instagram exhibitionists, white water rafting in Patagonia. Or we’re tie-dyed New Age Yoga Hags, downward dogging it in Belize.

We give our alter-egos test balloon flights, touchdown in one place, skitter along, and then get swept into the next updraft and carried away again.

Manhattan was the patient groom in my unspoken arranged marriage, the implicit goal of any tri-state suburban childhood. Yet, growing up in the seventies, I feared New York, took the expression “no news is good news” literally. Local nightly broadcasts were filled with murders and kidnappings—lots of news, none good.

Could I ever grow to love this, I’d think, my crisp intern ensembles wilting in the putrid Manhattan summertime steam bath?

After I moved to Washington, D.C., then California, I returned to weep on the city’s shoulders through heartbreak, romantic and otherwise; it was my rock, my steadfast Colonel Brandon. “Take your time; I’ll wait,” it seemed to reassure me every year. Yet, as soon as I arrived, I felt constrained, restless. I hated the concrete, cursed the teeming masses who looked just like me.

I think I kept returning hoping to find the adult I was supposed to grow into, the hardened, sharp-elbowed, competitive, citified version of me. After decades trying to make it work, I realized why it was so hard to let go: saying goodbye to New York meant saying goodbye to that “me” who never was. I’d somehow escaped my own destiny.

We search high and low to find ourselves; but maybe, when we pause and repeat, pause and repeat, we’re finding little pieces, snapping them in place. Some people know their own minds early, others of us are slower to arrive at our final destination. Maybe we never really do.

Hawaii is a puzzle I never tire of; geographically convenient to my West Coast home, and thousands of miles and an ocean away from my birthplace. While I know Hawaii’s back roads and shortcuts from almost twenty years of annual visits, nobody knows me there. I can find the best marlin poke (at Foodland, you’re welcome), yet lose myself in a tropical daze.

As with any alluring passion, it’s Hawaii’s mystery, what I can’t know, that perpetually pulls me in. Attraction is about how we feel together; in Hawaii, I’m always on the wrong side of inclusion, drawn to the effortless warmth of Ohana — family—that’s part of the culture. It’s both recognizable and alien.

Hawaii’s invisible wall separates visitors from islanders; we exist on parallel planes.

On a beach on a Sunday, pale once-in-a-lifetimers cower in shaded cabanas while cartoon-cute toddlers squeal on boogie boards yanked stop and go along the tide line by older siblings lost in uncomplicated, shared glee.

Once a month, my favorite resort breaks through this barrier, staging an evening of stories and music on a close-cropped grass carpet between the jagged black lava and the sloshing sea. Along the porch of a historic green-and-white trimmed cottage, grandpas playing ukuleles admire their grey haired wives scooping figure eights with their hips in the breeze. The black, starless sky creeps over the muddled sunset that stains the waves purple before melting away.

Locals arrive with deviled-egg platters, kissing and catching up and apologizing when one of their sleeves grazes your cheek as they lean to greet a cousin or friend. Sitting so close, even on my hotel towel, it almost feels like being a part of it, of something outside of and bigger than “me.” Maybe it carries me closer to that hotel experience imprinted on me in infancy. Or maybe it’s as close as I’ll get to being part of this island’s hanai, the extended family.

One night, a Hawaiian “Auntie” arrived, and began bestowing fragrant hand woven haku leis—Hawaiian head wreaths—on her female friends.

She padded closer, pulled out a wreath, pressed it to my forehead. Was this a mistake? She tied the white ribbon, smiled warmly, adjusting the vibrant blooms. My world instantly shrank to a gesture; I glanced up, saw wisps of leaves quivering above my eyebrows and was transported further than on any previous trip. For a flash, I grasped the Holy Grail of my endless tap, tap, tapping on the door. Here I was. I was in.