Choose Your Own Driving Adventure

We detail some special adventures you can take

Whatever your automotive proclivities, we’re here to help inspire your next grand outing. Apart from our own travel adventures covered in this issue, here are four more of our favorite offerings worth checking out.

Cruisin’ Hawaii

It can be tough to steal away for some me time on a family vacation—and even tougher if you want to use that time to satisfy your gearhead cravings. Sure, it’s easy to find a golf course, pool, or beach, especially in Maui or similar retreats, but Hawaii isn’t a place you likely think of as a driver’s destination. As a recent outing to The Valley Isle revealed, though, paradise can provide a surprise.

David Gentry, who runs his operation via peer-to-peer car rental services DriveShare and Turo, and his partners, Moonstar Greene and Yuri Soledade—proprietors of the Paia Fish Market restaurants—are the kind of people who find a way to do what they love regardless of locale.

Gentry is a scrappy dude in his early 40s who, when not waxing rhapsodically on the virtues of short-throw gearboxes, works as a commercial contractor. He talks mostly about the objects of his passions: his fleet of cars. It isn’t big, but it includes a 1974 Alfa Romeo GTV 2000, a 2012 Porsche Cayman R, a 2002 Lotus Elise, and a slew of late-model and vintage Minis.

So drive we did, along with Gentry, Soledade, and Greene. Up and down and around the island, we switched between the Porsche, the Lotus, and the Alfa. Even among weapons like the Cayman and Elise, it was the aged and finicky Italian classic that spoke volumes. Coming down the dormant volcano Haleakala in a cold, sideways rain, shifting through the gears, it finally felt like this was the vacation we’ve always sought.

For more information:

Cars: DriveShare.com and Turo.com, prices vary

Hotels on Maui: Andaz Maui at Wailea Resort; Maui.Andaz.Hyatt.com

Hotels on Lanai: Four Seasons Resort; Fourseasons.com/Lanai

Top tips for planning a similar experience:

Rule 1: Book a hotel you know the family will love even when you’re not there. We went for the Andaz Maui at Wailea Resort, knowing the family would be happy enjoying the mahalo beach vibes.

Rule 2: Do a lot of research. Gentry offered to take us on a guided tour of the island, but usually he’ll simply tell you where to go and how long it will take. The internet is your pal and kept us away from the torturously slow Road to Hana. For the right wheels, book early. The prices on Turo and DriveShare vary, but expect to pay a few hundred dollars per day for a whip like the Lotus and up to a thousand-plus for an exotic, insurance included.

Rule 3: When all else fails, ask the hotel concierge, as they can set up almost anything and everything for you, including guided tours. That’s what we did at the Four Seasons Resort Lanai; an hour later and a few hundred dollars lighter, we were bombing red-dirt back roads in a Polaris RZR side-by-side.

Ultimate Driving Tours

UltimateDrivingTours.com; Prices start around $8,000

Forget your local supercar rental lot; Ultimate Driving Tours is the real deal. The Australia-based tour company offers an incredible assortment of driving packages stretching across three continents. Each program is meticulously planned with overnight stays at specialty resorts, meals at top-tier restaurants, and an occasional visit from a racing legend like Jackie Stewart. Its fleet of available cars is impressive, ranging from workaday favorites like the Ford Focus RS to grand tourers like the Mercedes-AMG GT to supercar royalty like the Ferrari 458 Speciale. Prepackaged road, racetrack, winter, and motorsports tours are available in Europe, Australia, and the U.S. If you want something more personal, Bring Your Own Car (BYOC) and bespoke packages are available.

Grand Prix Tours

GPTours.com; Prices dependent on event and options

Before stressing over the itinerary of your next motorsports getaway, give Grand Prix Tours a call. The travel experts at GPT offer all-inclusive packages for most major global motorsports events, stretching from the Azerbaijan Grand Prix to the Indianapolis 500. GPT is especially known for its Formula 1 hospitality bundles, covering the majority of the annual F1 schedule. Each package is mostly a la carte, offering different levels of admission, amenities, and hotels. And if you already had a blast at one of its four-wheeled adventures, make sure you check back in for one of GPT’s MotoGP or golf trips.

Safari Drive

Safaridrive.com; Prices start around $3,000

Not every petrol-powered vacation has to be turbo-charged and Michelin-starred. If you’re of a more adventurous disposition, check out self-driven tours through Africa via Safari Drive. For more than 20 years, these overland experts have put drivers behind the wheel of Land Rover Defenders and Toyota Land Cruisers on fabulous curated tours through some of the wildest country in the world. Interested parties can pick from seven African countries (or Argentina) and enjoy multiweek 4×4 excursions that span from cushy, coddled resort relaxing to rooftop camping in the wilderness.