Million $ Road Trip
In PREPARATION FOR THIS ARTICLE, I did what any dedicated journalist would do—I poured out a glass of wine and binge-watched every great road trip film I could think of. At first, it was just an excuse to sink into the couch as deeply as Jack Nicholson sank into his Harley in Easy Rider, but somewhere between the rolling landscapes of Sideways and the jazz-fueled wanderings of On the Road, the idea of a new kind of road trip took shape. Not the Chevy Chase slapstick kind, with broken-down station wagons and ill-fated amusement parks, but something bigger. Something legendary.
This is not the road trip with questionable motels, gas station burritos, and a backseat overflowing with fast-food wrappers. This is the Million $ Road Trip. The perfect ride, the perfect soundtrack, the perfect booze. It’s a road trip where yachts, high-stakes tables, and midnight speakeasies share the road with mile-high pies and campfires: a Kerouac novel reimagined with a limitless expense account, if you will. And through it all the highway rolls out ahead of you daring you to put the pedal down.
Itinerary: Chicago To Las Vegas
THE CAR
EVERYONE KNOWS you can’t have the perfect road trip without the a glass-walled palace overlooking Lake Michigan, complete with a perfect car.
Option 1: A 1968 Ford Mustang GT Fastback—a beast reminiscent of Steve
McQueen in Bullitt that will set you back at least $250,000+ at auction.
Option 2: A custom Porsche 911 Carrera Cabriolet ($133,400++), for
those who prefer something sleeker, faster, and with a little less growl.
THE STYLE
Observatory, a private room designed like a billionaire’s library, A vintage Steve McQueen leather jacket ($40,000+ at auction) and where a $1,000 minimum buys you rare spirits, caviar, and a view of a pair of Ray-Ban Aviator Solid Gold sunglasses ($4,245) bring that requisite Hollywood cool. Strap on a TAG Heuer Connected Calibre E4 Porsche Edition ($1,650) - a smartwatch that connects with your Budget two days to take in the city, then it’s time to get on the road for a mosey along America’s most famous road: Route 66. ride, checks your Porsche’s fuel levels, adjusts the A/C before you get in, and makes you look like you know things about circuit racing. And with that, we hit the road. Chicago to Vegas, no compromises, no limits.
CHICAGO KICKOFF
Check into the Four Seasons Presidential Suite ($12,000 per night), a personal concierge to make sure no request is too outrageous.An exclusive Frank Lloyd Wright excursion—booked through the hotel ($1,000/person)—draws you into Chicago’s history, while dinner at Ever ($1,020 for two) ensures that the first night on theroad is anything but ordinary. After dinner, slip into After, one of America’s best cocktail lounges. The Observatory, a private room designed like a billionaire’s library, where $1,000 minimum brings you rare spirits, caviar and a view of the stars through a vintage telescope.
St. Louis
CIGARS, SPIRITS & THE MISSOURI RIVER
A FEW HOURS ON THE ROAD AND YOU’RE IN ST. LOUIS. After stopping at Daniel Schmitt & Co. members with reservations. Go for the to admire (or acquire) a rare classic car and to 10-course tasting menu that can be upgraded learn about St. Louis’ rich automobile history, with wine pairings, caviar service, and a cheese check into The Ritz-Carlton ($715/night)—home flight for $444 per person. to the last Ritz-Carlton Member’s Cigar Club in the world. Settle into a leather chair, light up a Davidoff Millennium Blend Robusto, and do some damage to a bottle of Rémy Martin Louis XIII ($4,485)—or put that concierge to the test and see if he can acquire an ultra-rare bottle of Macallan 1946 ($75,000) for the occasion. The next day, head 45 minutes west to Augusta, Missouri, and board the Miss Augusta Yacht, a 105-foot luxury cruiser offering private charters on the Missouri Riv Texas To New Mexico.
WHISKEY & WILDERNESS
THE NEXT LEG OF THE MILLION $ ROAD TRIP swaps city skylines for wide-open ranchland, rugged mountain retreats, and the kind of whiskey-soaked nights that belong in a Western epic. From the five-star frontier luxury of JL Bar Ranch to the remote wilderness of Vermejo, this stretch is about rolling landscapes, rare spirits, and a little cowboy mythology. Turn up the music, take in the view, and ride this one out in style.
Arriving in Sonora, Texas, the landscape shifts from open highways to 13,000 acres of ranchland, signaling the approach to JL Bar Ranch, Resort & Spa: a secluded escape with private airstrip access designed for CEOs, celebrities, and high-end travelers.
Saddle up for horseback riding, clay shooting, and guided game hunts during the day, while the evenings offer mesquite-grilled wagyu, wine tastings, and unwinding by the firepit with a cigar. The Archer’s Nest Villa has just the right blend of frontier adventure and five-star indulgence, including a resort-style pool, outdoor kitchen, and a private home theater. (approx. $17,200 for five nights)
Santa Fe
THE NEXT STOP IS SANTA FE. Stop by Shiprock Santa Fe for rare Navajo textiles, fine jewelry, and museum-quality Indigenous art, or visit Manitou Galleries, where collectors can acquire exquisite Native American and contemporary Western pieces, from intricate turquoise cuffs to bronze sculptures fit for a private estate.
Dinner is at Sazón, an intimate, James Beard Award-winning restaurant, that offers a curated tequila and mezcal tasting, alongside their new world cuisine, featuring ultra-rare bottles like Clase Azul Ultra Añejo ($3,000 per bottle) and Codigo 1530 Extra Añejo 13 Year ($3,999 per bottle). The De Los Dioses tasting flight—which includes Fuenteseca 21 Year, 1993—gives you a sip of all three for $500 per person.
For a stay infused with the spirit of New Mexico, head to the award-winning The Inn of the Five Graces,which is known for its epic spa and southwestern hospitality. As stunning as the rooms in the inn are, for a bit more adventure we recommend booking a glamping experience in a high-altitude camp (starting at $9,080 per couple, excluding taxes and gratuities.) If you’re lucky, you might even sleep beneath the Taos Perseid Meteor Shower.
From Santa Fe, head just south to Albuquerque for a campy detour into Route 66 history. Even the most indulgent road trip needs a proper greasy spoon stop, and there’s nowhere better than Lindy’s Diner. A colorful time capsule that hasn’t lost its sense of humor, the diner serves up burgers with names like the “Blue Baller” (covered with blue cheese crumbles, of course) and the Fat Bastard (with a fried egg, bacon, and your choice of cheese) as well as their famous pies and “damn good” coffee. This stop is pure Route 66 magic—and a reminder that some of the best meals on the road don’t need white tablecloths or a Michelin star.
From Albuquerque, the road stretches past truck stops and fast-food joints and into the wild expanse of northern New Mexico, where 550,000 acres of untouched wilderness await at Vermejo, Ted Turner Reserve. 10,000 feet up into the Sangre de Cristo Mountains, you’ll find the Costilla Fishing Lodge, Vermejo’s most secluded retreat. Spend five or more days casting for Rio Grande cutthroat trout in alpine lakes, hiking to hidden waterfalls, and spotting roaming bison, while evenings bring five-course gourmet meals crafted by a dedicated chef. With expansive mountain views, a grand stone fireplace, and total privacy, Costilla Fishing Lodge is the perfect American escape.
Arizona to the Grand Canyon
DESERT LUXURY & HIGH-STAKES SKIES
From the quiet seclusion of the desert, the adventure as cinematic as the journey through Arizona’s red rock shifts skyward. A private helicopter from 360 landscapes and into the neon glow of Nevada. Adventures ($9,450 per flight) departs from Scottsdale Airpark, offering an exclusive aerial tour over Sedona’s
In the Sonoran Desert just outside Phoenix, Castle Hot Springs ($4,000 per night) was once the private retreat of Rockefellers and Roosevelts. This remote oasis now serves as the ultimate place to wash off the road dust in open-air soaking tubs fed by natural hot springs. A seven-night stay will give you a good dose of desert luxury, with days spent hiking through the red rock landscape, off-roading through the rugged terrain, sharpening your axe-throwing skills (really), and sipping cocktails after a hands-on mixology class. But nothing tops the hot springs themselves, cascading into pools of varying temperatures, and rumored to possess centuries-old healing properties.
As the sun sets, sink into the warm waters with a glass of small-batch tequila and raise a toast to the road behind—and the indulgence still ahead. Red Rocks, Marble Canyon, and the Colorado River before touching down at Grand Canyon Airport for an immersive private tour. For those wanting more than just the view from above, a four-hour private hiking tour ($1,650 additional per tour) includes a gourmet picnic lunch, before soaring back over the San Francisco Peaks and the Coconino National Forest. For those who want to extend their time in the air, additional flight hours are available at $190 per hour.
Vegas, Baby
NO MILLION $ ROAD TRIP IS COMPLETE WITHOUT A BLOWOUT STOP IN LAS VEGAS, where the only rule is more—more indulgence, more champagne, and more ways to push the limits. After days of cruising through cinematic landscapes reconnecting to echoes of America’s past, soaring over the Grand Canyon, and soaking in desert hot springs, Vegas marks the final crescendo.
Check into The Empathy Suite at the Palms ($100,000/night for the next four nights), a 9,000-square-foot Damien Hirst-designed penthouse, complete with a private cantilevered pool, original Hirst artworks, and a 24-hour butler. From here, the indulgence continues with a private menu prestige dinner at Restaurant Guy Savoy ($1,000/guest). Start with a magnum of Louis Roederer, Cristal, Reims, 1995 ($4,900) to share with the friends you’ve inevitably met along the way, then ease into a Grand Cru Domaine de la Romanée-Conti, Le Montrachet, 2000 ($15,000) with your Savoy’s version of surf & turf, which, of course, is far from Vegas’ surf & turf buffets of old.
After dinner, the night is just beginning. Whether it’s securing a VIP table at Drai’s Nightclub with a $50,000 champagne package or taking in a headlining show from rock legends like Rod Stewart or Bruno Mars (VIP front-row seats range from $1,500 to $15,000+), the night is all about high-energy luxury. For those looking to push their luck, Wynn offers the highest-limit table games in the city, with $100 minimum bets for blackjack, baccarat, and pai gow tiles, while European Roulette and high-limit blackjack start at $200 and up. And you’re all set to try your luck and blow through your last 100k.
As the final stop on the most excessive road trip ever mapped, Las Vegas is the only place to go all in. Whether you’re sipping rare bubbly in a private lounge, rolling high-stakes bets at a secluded casino table, or watching the Strip blur into the morning light from your penthouse balcony, this is where the journey hits its ultimate high note. If you’re going to spend a million dollars on the road, you might as well end it with a bang.
All that’s left to do after the party winds down is hire a private driver to handle the return trip, step onto the tarmac, and board
your private jet home.