Does the Car Make the Trip?

Finding the right car that matches your destination.

A few weeks ago my friends over at The Wm Brown Weekly posted my write up on renting the right car for the right vacation in Bulletin Board 54. Reposting it here…tell me if you have a similar need to match your wheels to your destination.

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Land Rover Defender at Sunset; St. Barth.

When I travel somewhere that requires a rental car, I see it as an opportunity. Not just to get from A to B, but to pick something that fits the place. Context, design, your agenda…to me, it all matters.

A good road-trip car is more than transportation. It’s a traveling companion, a mobile home base, and a bit of entertainment. Sometimes, if you choose right, it makes the trip.

Here are three drives that have stayed with me.

Italy
Rome to Milan in an Abarth 595

Abarth 595; Tuscany, Italy.

Plenty of people travel Italy by train. It’s convenient. But you miss a lot: small towns tucked in the hills, off-the-beaten-path gems, wineries, and my personal favorite: Autogrill, the roadside service stations with espresso and food far better than you’ll find at any other rest stop.

On a recent one-way trip from Rome to Milan, I had days planned in Umbria and Tuscany before heading to Modena for the Ferrari Museum and ending with a few days in Milan. I needed something compact for chaotic cities and medieval villages, but still rewarding on the autostrada. Parking in Italy can be its own sport, so small was a must.

Hertz’s “Selezione Italia” had the answer: an Abarth 595. Essentially a Fiat 500 that’s been to the gym: more horsepower, tighter suspension, sharper brakes, and a proper manual gearbox. Luggage space? Let’s just say if you’re traveling with more than two people and a couple of bags, you’ll have problems. We made it work.

The Abarth was exactly what I hoped for: sharp in the curves, a blast through tunnels, and just cheeky enough to turn heads. A hotel valet in Umbria whistled when I pulled up, always a good sign. It fit right in outside Massimo Bottura’s rural hotel with its incredible car collection, and even parked outside Scuderia Ferrari HQ. I’d like to think it held its own.

Pulling out of Milan in a dusk rainstorm, dodging construction detours, it felt composed, even fun. Dropping it off at Malpensa Airport, I realized the Abarth had become part of the trip itself.

Norway
Fjord Country in a Porsche Taycan

Porsche Taycan; Norway.

Norway has the highest per capita EV sales in the world. I’m a combustion guy at heart. To me, heritage and mechanical soul matter to me more than software updates…but, like I said, part of the fun of picking the right car is matching it to the place.

TRIPS of Norway, who also do production logistics for big film and TV shoots, delivered a Porsche Taycan to my hotel. All-electric. My first extended drive in one. The fjords are remote, so I had some range anxiety. Completely unfounded as it turned out that charging stations are everywhere, and most hotels have them.

The Taycan was a perfect fjord grand tourer. It carved up mountain switchbacks and slipped onto ferries like it belonged there. Instant torque meant every stretch felt alive, though Norway’s famously brutal speeding fines kept me honest.

I had only a few days with it, but it left a mark. The quiet, the design, and the way it made the landscape feel even bigger. It’s so different from anything else I own and drive.

St. Barths
Island Life in a Land Rover Defender

Land Rover Defender; St. Barth.

St. Barths is small, only nine square miles, but it’s hilly, spread out, and taxis are scarce. Most visitors rent small hatchbacks (think: Kias, Minis) or a Moke…the retro beach cruiser with no doors and no AC.

Years ago, I connected with a small outfit renting Defenders on the island. On paper, it’s the wrong tool for the job. Narrow roads, tight parking, and far from nimble. But, in practice, it’s perfect. You bounce between beaches and hillside neighborhoods, wet towels and sand in the back, canvas sides rolled up, salt air everywhere.

Cruising into Gustavia in a Defender feels like you belong. As a photographer, it’s also a dream subject, especially parked near the airport with planes dropping in just feet overhead.

The Defender has become part of my St. Barths tradition. I even registered my Defender at home with the same plate number as one I rent there. A small piece of the island that lives in my garage.

The Extra Step

Finding the right car for a trip takes more effort and often a little more budget. But for me, it’s worth it. When I plan a trip, the checklist is always: flights, hotel, restaurants, and car. The last one matters just as much as the rest.

Abarth in Umbria. Porsche on a Norwegian Ferry. Land Rover Defender in St. Barth.

If you’ve ever had a trip where the car made it better—maybe even made it unforgettable—I want to hear about it. Where’d you go? What’d you drive?