vintage red car parked outside of havana cabana in key west florida

I am not a motorhead. And yet, road trips continue to captivate me — even short ones, such as the timeless ride with my children from the doors of evocative Sheen Falls Lodge to downtown Kenmare Ireland (just minutes away) in the back seat of a gorgeous 1936/1937 Buick Phaeton convertible, the house car, marvelously painted the color of County Kerry’s countryside. Like a prop, a car can add an element of fantasy to a trip— isn’t fantasy one of the reasons we travel?

I’ve been picked up in a Bentley at a London hotel to gadabout in the Cotswolds, swerved the curves of Lake Como in a red Alfa Romeo, rented a Jaguar to go wine tasting in Napa (designated driver included), guided a 1956 Porsche 356 A Speedster from Cap du Ferrat to Milan, and driven in a convoy of BMWs along one of Relais Châteaux hotels’ “Routes du Bonheur (circuits that link their gastronomic hotels), eating and drinking at a variety of inns along the way.  

Up next? I think I’ll take Tivoli Hotels & Resorts Timeless Tour, created to celebrate their 90th anniversary. Steering a classic vintage car (species to be determined), I’ll begin in Lisbon at Tivoli Avenida Liberdade — the birth of the brand’s history — before driving along scenic roads to experience  Tivoli Carvoeiro and Tivoli Marina Vilamoura in the Algarve on a tailor-made tour organized by the hotel’s concierges. Ready to roll? We have some other engine-starting ideas for those with a penchant for road tripping in style this summer.

Château Louise de La Vallière, Loire Valley

chateau louise de la vallière in loire valley france
Courtesy of Château Louise de La Vallière

France’s Loire Valley’s forests, chateaux, undulating roads, and awe-inspiring villages are best seen by automobile. With that in mind, Château Louise de La Vallière, an extraordinary five-star hotel just minutes from Tour and Amboise, offers guests the opportunity to ramble into the landscape by motor car, as giddy as the kings and queens that rode through it on horseback or by coach in centuries past. Borrow their prodigious Morgan, a worthy ride for the regal set. As you navigate past vineyards and castles, consider the rareness of a Morgan. Only 850 cars are produced each year, each assembled by hand. Back at the chateaux, revel in the spellbinding bygone glamor as the hotel embraces the past via period costumes and more.  

Havana Cabana Resort, Key West

closeup of a motorcycle facing a pool and palm trees at havana cabana in key west florida
Courtesy of Havana Cabana

Hemingway vibes (including his famous six-toed cats), the scent of rolled cigars and coconuts, flamenco music, and the whisper of sails in the wind comprise Key West’s distinctive allure. From lime-y Mojitos to a reverence for classic cars, Havana Cabana, an adults-only retreat, takes inspiration from nearby Cuba to offer Jimmy Buffet barefoot chic fused with the exotic. Begin your authentic Havana Cabana experience with celebrity-style airport pickup by vintage 1957 Chevy Bel Air. After beach time, hop into one of the resort’s several mid-century Chevy cars to survey downtown Key West, a fount of art and culture. 

Casetta Firenze, Tuscany

It’s not a cliche. The owner of Casetta Firenze prides herself on welcoming guests like family. Owner Xenia Lemos not only opens the doors to her 270-year old, opulently refurbished farmhouse, but also offers you the keys to a sultry collection of cars. Drive through Chianti’s rolling countryside like a true Tuscan in a fiery Ferrari or vintage Fiat 500 to visit local vineyards on an itinerary of VIP tastings organized by Xenia herself. Return to the castle for late afternoon repose and a decadent dinner. Also possible when not putting the pedal to the metal? Truffle hunts, equine therapy, cooking lessons, and more. 

Phāea Blue Palace, Crete

a vintage white car parked near phaea blue palace in crete greece
Courtesy of Phāea Blue Palace

There’s always somewhere quiet to escape to on Crete, Greece’s largest island. With more than 3,000 square miles of breathtaking landscape, it brims with hidden nooks. Find them on a Classic Car Village Tour organized by family-owned Phāea Blue Palace, an exemplary holiday retreat. Tucked into a vintage Mercedes or Cadillac  — bikini in your purse, cameras, and sandals at the ready — you’ll be transported back in time on a journey that surveys some of Crete’s most characteristic islands. Stop at the mystical Areti monastery, lunch at Platanos, sip coffee in Kasteli, and circle back to the resort through the port city of Neapoli and stunning Agios Nikolaos. 

Fuji Speedway Hotel – The Unbound Collection by Hyatt, Oyama Japan

Gearheads can rub shoulders with other aficionados and professional racers at the car-themed, luxury Fuji Speedway Hotel – The Unbound Collection by Hyatt, located in the foothills of Mt. Fuji. Positioned on the grounds of Japan’s historic racing circuit, Fuji Speedway, the 120-room hotel houses the Fuji Motorsports Museum. With rooms that overlook the racetrack, the hotel offers a variety of racetrack adventures, including the Circuit Experience, in which guests can drive three laps around the track in their own car. 

Rome Cavalieri, A Waldorf Astoria Hotel, Rome

a blue vintage fiat with the top down parked outside of rome cavalieri a waldorf hotel in italy
Courtesy of Rome Cavalieri, A Waldorf Astoria Hotel

You’ll feel as Roman as cacio e pepe when you speed through the streets of The Eternal City in a vintage Fiat with a driver and personal photographer in tow. One of Rome Cavalieri, A Waldorf Astoria Hotel’s many immersive experiences, this customized car tour of Rome, aptly called “La Dolce Vita – FIAT 500 Spiaggina Experience”  presents the city through Roman eyes. End your  Fellini-like quest to see all the sights with an Aperol Spritz in the hotel’s lauded gardens as you thumb through a keepsake photo album that recalls the day.  

Mandapa, a Ritz-Carlton Reserve, Bali

Famously spiritual Bali captivates, inviting travelers to stillness, self-awareness, and self-discovery. But leave inner reflection (and the quietude of this sublime resort) aside for a bit to take a field trip. Bump along Bali’s back roads in the beach-buggy-like VW 181, an apropos vehicle for island touring.. On a program designed by Mandapa, a Ritz-Carlton Reserve’s able concierges, you’ll pilot “The Thing” (as the car is nicknamed) on a daylong adventure to see lesser-traveled sites — such as Tirtal Empul water temple and 11th-century  Gunung Kawi, known as the Valley of the Kings.  A picnic with a view goes without saying.

Metropole, Monte-Carlo, Monaco

vintage red car with the top down on display at hotel metropole, monte carlo in monaco
Courtesy of Hotel Metropole, Monte Carlo

Home to Formula 1 and exotic sports cars, Monaco has a web of narrow, winding streets prime for parading its extravaganza of exotic vehicles. Expect to see superlative models from DeLoreans to Ferrari 612 Scagliettis wedged into tiny parking spots or on the road for ordinary errands. When not zooming around corners in your own peerless auto, enjoy Hotel Metropole Monte-Carlo’s exclusive Drive Through Time which allows access to the Prince of Monaco’s palatial garage, full of more than 100  iconic cars  — from a Chrysler Imperial to a Rolls Phantom, as well as a variety of Formula 1 models. The tour, led by an expert guide, provides the opportunity to open and see inside some of the vehicles, as well as hear fascinating stories about the Grimaldi family.

The Beverly Hilton, California

Dress in your best Edith Head gown to gallivant behind the wheel  of a 1950s Corvette or a 1960s Cadillac like a star-studded silver screen siren of yore. Partnering with Hollywood Classic Cars The Beverly Hilton  (ever divine) offers The Golden Getaway package, an opportunity for romantics to take the wheel for a titillating afternoon that pays homage to the hotel’s Golden Age history. Along with car time, you’ll spend the night in the illustrious Penthouse Suite, have photo shoots, and enjoy an en suite gastronomic dinner, personally curated by the hotel’s executive chef, Matthew Morgan. 

Featured image courtesy of Havana Cabana