Want to Buy a Classic Defender Overseas? Learn From My Mistakes.

The plan, at least within my car-addled brain, sounded perfect in theory: buy a car in Italy and avoid rental fees by touring the country in it with the family for weeks, then ship the steed back home and sell it for a tidy profit. Being a chronic Land Rover addict, one particular model seemed to tick all the boxes—a classic Defender.

Not only would an old-school Defender 110 provide enough space for the four of us and our luggage while crisscrossing from Como to Florence and parts in between, its rudimentary mechanicals should make it relatively straightforward to keep running, and its coveted status back home would make it easy to sell.

I must have a knack for making a higher power laugh, because my plans went sideways even before my misadventures began. I touched down in Milan to pick up the family truckster from a transplanted Brit with an automotive resale business in Piacenza. His 1992 Defender 110 seemed to have all the right stuff: it was a left-hand drive model with a bulletproof 200 Tdi diesel engine, a rust-free body, and a striking matte-silver paint finish that set it apart from the sea of sun-bleached Defenders so common across European cities. The seller came highly recommended from several friends who had imported vehicles from him. Even better, the price was right, so I proceeded on the assumption that I was in good hands. After a few calls and a dozen or so low-res images, we organized a rendezvous just ahead of the Concorso d’Eleganza Villa d’Este—a mere 90-minute drive away from Piacenza, though probably longer in the pokey Defender.

Excitement mounted when the dealer picked me up from the airport and we pulled up to the shop where my car-to-be was supposed to have completed a tune-up and inspection. Upon arrival, it seemed the mechanic had been enjoying a tad too much dolce far niente: the Defender was in pieces and clearly not ready for its close-up, let alone miles on the road. My seller was exasperated, and I was unsettled. How would my peripatetic vacation plans proceed without wheels? The dealer bore down on the wrench and demanded he piece it together then and there, while also offering to refund my money. Without a backup plan beyond a 1980s-era Bentley T2 that had caught my eye in a nearby neighborhood, I stuck to the original vision.

A test drive, though, revealed deeper issues. The vehicle wandered across the road far more than any already ill-handling Defender should, its brakes were weak, and gear shifts were accompanied by a prominent clunk. Other disconcerting maladies included non-operable windshield wipers and a flickering water-temperature gauge. Left with dicey alternatives, I told the seller I would proceed if he could address the issues; he agreed and rolled up his sleeves, then washed and prepped the truck so I could at least get to Lake Como before returning to get its needs sorted.

I’ll admit that piloting a classic Defender to my favorite concours on the planet felt inimitably cool. But with the directional stability of a jellyfish, that disconcerting clunk, and the panoply of other issues, my Landy would need considerable TLC before I’d feel safe transporting my family in it. After the concours, my seller commissioned further work at a different shop, where the decades-old Defender received new brakes, suspension components, and fresh tires in time for me to scoop my family from the airport in the sort-of-fixed truck in the nick of time.

While I’m often guilty of defending classic Land Rovers as being more reliable than their reputation might suggest, I got the sinking feeling that my purchase had been sitting undriven for quite some time; not a great thing for any vehicle. In our case, this was a potential vacation wrecker. With Rome, Florence, Venice, and eventually Genoa (to ship it home) on the agenda, we needed this ancient tractor to convey us safely, securely, and without fail.

The only trouble with the follow-up repairs was that the Landy’s considerable needs weren’t fully addressed in time, throwing a further wrench in my plans. The seller recommended a mechanic once we arrived in the Eternal City, and I came to the grave realization that at least part of my family vacation would become a rolling restoration for our newly acquired bottomless pit of mechanical wants and needs. Perhaps foolishly, we anointed our four-wheeled friend a name, a surefire way to develop an irrational attachment: we christened it Za, after the first letters of its license plate.

Driving this plus-sized terror through an ancient European city can make you feel like a modern-day emperor. The Defender’s large footprint is justified by its considerable luggage capacity, but at the end of the day, the challenges of needling the 110 through narrow roadways and squeezing it into tight parking spots can become a chore. Furthermore, the lack of air conditioning made it feel that much scorchier at the height of Italy’s toasty temps. As for road noise at highway speeds (once it reluctantly ambled its way there), let’s just say that conversations turned into yelling matches.

What the Defender lacked in basic creature comforts it made up for in personality, at least on the rare occasion when it was running right. One memorable moment came when my wife had a business meeting at Cinecittà, the film studios made famous by everyone from Federico Fellini to Michelangelo Antonioni. Catching a glimpse of an ancient Roman backlot while driving through the sprawling property, I defied her request to stay on the beaten path and diverted across the cobblestones that run through a re-creation of old Rome. We also traveled to one of our favorite Tuscan villas, Villa Torrigiani, making countless stops in between—from an Eataly restaurant at an Autogrill service station to our monthlong stay in Florence.

Annoyingly, the Roman mechanic recommended by the seller was unable to solve the weak brakes, which required me to keep my distance and anticipate stopping ahead of time. A few other niggles lingered, including some electrical issues and the thunking sound. I thought I’d just deal with it, but when I least suspected it, I experienced a full and complete failure to proceed in Florence. Stopped on a busy uphill boulevard, a few miles from our temporary residence, I took a chance during a break in traffic and let the truck roll backwards before popping the clutch. Voilà, it fired right up, so I drove it closer to home to figure out my next step. Thanks to the miracle of Google Reviews, I was able to locate a highly rated mechanic nearby. More amazing, however, was what materialized a mere 20 minutes later: Angelo Zarbo, a German mechanic riding pillion on a BMW motorcycle and clutching a battery starter.

The good news: Angelo’s shop was a reassuringly pristine spot working on high-quality vehicles, from a classic MG to a contemporary Porsche. Even better, he was a former wrench for Kremer Racing in Germany and BMW racing in the U.S. The bad: my seller refused to cover any further repairs on the Defender, even though most of the truck’s original issues were still not resolved. While my Defender was being worked on by the mechanic du jour, we got around in Ubers, on foot, and for longer jaunts, by train. After days under the knife and a substantial repair bill, the truck was ready to be picked up in time for our next destination. It drove better, but the steering wheel now cocked at an absurd angle and the brakes were still not working properly despite an array of new parts.

By the end of our Italian tour, we had completed approximately 1,000 loud and bumpy miles in the Defender. Despite the agricultural driving experience, the flawed mechanicals, and the irritating interruptions, we somehow developed an affection for the lumbering beast of burden. The Defender had been our companion across some of our most beloved Italian spots—through the pines of Rome, across the rolling hills of Monti Chianti extending through Florence, Arezzo and Siena, and the shores of Lake Como. When we finally pulled up to Genoa, our sendoff was bittersweet. The train ride to Venice offered time to reminisce on the miles of misadventures in our silver Landy, which was a ticket to freedom entwined in its paradoxical dependency on local mechanics. In a comedic twist of fate, the seller forwarded numerous photo tickets after our communications had soured; I offered to pay them, but the seller demurred.

A few weeks later, we met Za on the other side—Houston, a more viable port of call than California, which has the curious habit of holding up Defenders in customs. At least on a Federal level, importing the Defender was no problem because it was more than 25 years old and therefore exempt from stringent U.S. crash-test and safety requirements. However, it’s almost impossible for diesels imported to California to receive California registration. Sometimes they squeak through on luck, but the more common route is to hire a company to update the truck’s emissions equipment to the tune of $20,000 and months of work. After paying the California state tax at my local DMV and complying to a VIN inspection by the California Highway Patrol, my registration request was nonetheless denied by the home office in Sacramento.

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I resorted to out-of-state registration, finding a solution in South Dakota. I was also able to have my Landy worked on by my beloved local mechanic, who was finally able to troubleshoot the brake issue (my 110 had been equipped with the incorrect brake master cylinder from a 90 model) and solve the clunking issue by replacing worn suspension bushings. My guy was also able to remedy a load of other automotive ailments while discovering such unsavory details as the fact that the Italians used tap water instead of coolant, requiring replacement of the rust-infiltrated radiator and turbo intercooler.

Seeking the best rubber for our Za, I contacted The Tire Rack and connected with a specialist who reviewed a number of options. Intent on sticking to the truck’s off-road roots, while lending it an imposing stance worthy of its rugged capability, I opted for a set of BF Goodrich KO2s (full disclosure: delivery and installation was gratis). Sorting the correct size was not straightforward, as the Italian tires on the truck were oddly proportioned and on metric measurements. With no U.S.-equivalent model available for reference, I was offered in-depth, well-considered options for which profile, width, and brand would be best suited to the Defender.

In a small act of sprucing, I spray-painted the bolting nuts matte black so they set the wheels off more dramatically. Yet I was horrified to learn that the off-brand tires the seller had provided—installed in Italy just a few thousand miles previously—had developed a visible sidewall tear on the inside, which could have had catastrophic results at highway speeds—an important reminder that no-name rubber might save a few bucks, but at a potentially fatal cost. Wearing the new set of BF Goodriches, Za was safer and better-looking than ever in its new country of residence.

A funny thing happened on the way to flipping this car for profit: we fell in love. Despite our sincerest efforts to buy low and sell high, we had grown hopelessly attached to our imported Landy and felt it had become one of the family. It was so different from everything else on the road, so unapologetically individualistic, that we grew attached to the view through its letterboxed windshield despite its copious flaws. Our happiness led us to cling to the Defender far longer than planned, though we finally decided to part with the truck. We found a buyer who might have loved our truck just as much as we did. “I need to take stick-shift lessons,” he admitted, which made me fear he was more attracted to the idea of a rugged off-roader than its reality. However, he did in fact learn how to drive manual, and conveniently ended up taking possession of Za right around the same time we stumbled onto a considerably more modern (yet still appealingly retro) 2010 Range Rover HSE.

That silver Defender is inextricably linked to memories of our Italian adventure, and we still talk about Za like it’s a long-lost family member. I’m also in touch with the owner, and we have a pact to have first right of refusal in the unlikely event he decides he wants to move on. But with a U.K. stay on the agenda for this summer, I also wonder if another vacation vehicle might be in our near future.