Your Own Private Ranch

Planning a luxury adventure in Maui is all about exploring the possibilities.


Story by Ilima Loomis | Photography by Sue Hudelson

Maui Hawaii ranch vacationThere’s something about walking across a baking tarmac toward the heavy, mechanical roar of a very large engine, and climbing into the front seat of a sleek, black helicopter that makes you feel like you have options.

As the headset settles over your ears with a satisfying squeeze, and hands reach to help you into a five-point harness, your entire body vibrates with the thrumming readiness of this machine to carry you anywhere. When you glance at the pilot, he gives you thumbs-up.

Forget the narrow paths and prescribed lines of travel the earthbound must follow. Today, you think, we will fly.

Whether money can buy happiness is something I may never know. But I can say this — it buys you possibilities. And in this world of commitments and deadlines, sign-up sheets, overplanning, and scheduled reminders, few things feel more luxurious than the simple question Where shall we go today?

We glide up the slope of Haleakala, over Makawao town and beyond, to soar above the eucalyptus forests of Olinda. Zooming over ranch buildings and rolling pastures, we span a plunging gulch and begin a smooth descent, skimming over the billowing grass of an open meadow toward a little wood cabin, a wisp of smoke curling up like a beckoning finger.

Adam Quinn, luxury travel planner in MauiThe rotor wash kicks up a vortex of yellow grass as we touch down, and we sit for a moment while the engine cools, the shadow of the helicopter blades sliding over us slower and slower, until someone opens the door, and the only thing we can hear is the sound of wind blowing through grass, and the low crackle of a cooking fire. Real life feels a world away.

Crossing the pasture to greet us is Adam Quinn, a luxury travel planner for the kinds of people who arrive on Maui by private jet. We’re here to try his “heli-ranch tour,” an itinerary that combines helicopter sightseeing with lunch (prepared by a private chef, of course) and activities at ranch.

Quinn calls this tour a “conversation starter” for clients, and the conversation goes like this: What do you want to do? ATV tour? A guide will be waiting to meet you. Ziplining? Let’s head next door to Pi‘iholo Ranch Zipline. Plein-air painting? We’ll have supplies and an instructor ready to go. Hiking? Couples massage? Mountain biking? Tell us what you want, and we will make it happen.

Maui Hawaii ranch vacationAnd if what you want is the luxury of keeping your options open, Quinn can make that happen, too. “I’ve had clients who just say, ‘Yes: all of it,’” he says. For the indecisive traveler, he’s booked the full slate of guides, activities, and deluxe equipment rentals, keeping them all standing by for the day — just in case you change your mind about what you feel like doing after lunch. The price of having all those possibilities? “It’s a $50,000 to $60,000 day,” he says.

We’re interrupted by the sound of thundering hooves, as two cowgirls leading a string of trail horses ride in at a dead gallop, announcing themselves with a joyful “whoop!”

Horseback riding? I like where this conversation is going.

The riders slow their horses to an easy walk and rein them over to make their greetings. Our guide is Tamalyn Baldwin, head wrangler for Pi‘iholo Ranch, and a member of the historic kama‘aina family that owns these lands. Perched on her horse Badger, arms draped across the pommel of her western saddle, she cuts a flashy figure with her rhinestone-studded bridle, spotted deerskin chaps, and mischievous, cowgirl grin.

Maui Hawaii ranch vacationAfter we’ve made introductions and commented on the beautiful day, she sits up, scratching Badger’s neck as he chuffs nervously. “We’re gonna go let these guys smell the helicopter,” she announces, leading her string toward the incongruous machine.

I stand on the porch and take in the vista — yellow pastures rolling into dark swaths of forest; downslope, the thick carpet of sugarcane fields that seems to run all the way to the sea. Across the Central Valley isthmus, soft, white clouds have begun to collect on West Maui’s mountain peaks.

“I just can’t get over how pretty this view is,” sighs Laura Markison to her husband, Tim. Now part-time residents of Kahana, the Markisons have been Quinn’s clients for years, saying they like to get out and explore the island, but prefer their adventures “managed.”

And Quinn is an adventure veteran. Hiking, camping, fishing, and scuba diving were part of his growing up, and with a father who left the Marines to become a private pilot, summer vacations were spent airport hopping across the country. “Instead of packing up the station wagon, we’d pack up the Cessna,” he recalls.

Maui Hawaii ranch vacationWith the horses secured at an actual hitching post, Baldwin saunters over to the table with a clomp of boots and a jingle of spurs. Quinn starts pouring the wine as Chef Mark Shimer introduces us to our lunch: pulled short-rib sliders with marinated tomatoes, simple green salad drizzled with a spiced rum dressing, and potato salad with artichoke hearts and fresh herbs. Baldwin regales us with old rodeo stories, going over the finer points of calf roping as we tuck in.

Working with Quinn, Shimer says, is an adventure for him, too. “You can count on unusual locations with clients of high expectations.” Depending on the client and theme, the menu could be anything from our elegant picnic lunch to an elaborate evening of fine dining.

The cabin’s remote location presents its own set of challenges, Shimer notes, starting with the four-wheel-drive trek to get here. “Once you are in, you are in,” he says. “There is no corner store to save you if you left the butter in the walk-in. We must be prepared to cook over open fire, wood stove — as we did one Christmas dinner — or propane burners and by lantern light if the sun goes down.”

Maui Hawaii ranch vacationAs we drain our glasses and scrape the last bits of apple-berry crisp from our ramekins, Baldwin mounts up. Tim Markison has opted for mountain biking, and follows Quinn to the truck to pick up his gear. Meanwhile, the rest of us are fitted to our stirrups and given brief instruction in stop, go, and turn. It’s been more than a decade since I’ve been in a saddle, but I grew up on horses, and I relax into the seat, getting used to the feeling of reins in my hand again.

This trail ride is part of Quinn’s formula for a successful adventure: always move forward to something new; never backtrack. As we cut across open pastures and through cool forest, snaking along dusty Jeep roads and animal-trodden paths, I think about what a luxury that really is. For a moment, the back-and-forth world I live in seems very far away.

“Ready to run?” calls Morgan Rose, the twenty-year-old horsewoman leading our party. Laura Markison is not, and opts to finish the trip in the air conditioning and plush front seat of the ranch truck, which is escorting us from a discrete distance. The rest of us plant our butts in our saddles and give our mounts a squeeze, and my pulse quickens as I feel my horse surge forward with the group.

Soon enough, we’ll rendezvous with the gleaming, climate-controlled Mercedes Sprinter, standing by to whisk us back to our earthbound, within-the-lines, back-and-forth lives. But for the next few moments, I’ll relish the feeling of galloping toward the next possibility.

Adventure Quinn’s heli-ranch tour starts at $15,000 for six guests. To learn more, visit


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