Travel Smart:
Five Rules of the Rental Road

D id somebody say “car trip”? No, not the kind where you’ve got another 500 miles to make Tulsa before it gets dark and the kids throw up. A rental-car trip, after you land at the airport (and the kids have already thrown up). Trust me, it’s fun, and you never know where it might lead. Just follow this simple plan to get the most out of your motoring holiday:

1. Always rent a convertible

If you’re headed some place warm, that is (and always if you’re going from Miami to Key West). Why not? Think of a ragtop as nothing more elaborate than an upgraded stateroom, with a balcony, on a cruise ship. It only costs about $50-100 more a day to turn ordinary driving into a Route 66 fantasy.

2. Don’t skip the rental counter

Sure, it’s great to have gold status, which let’s you fly through the airport, right to the parking lot. But that’s for business travelers. You want to stop by the counter to chat up the clerk in hopes of an upgrade. Tell him how much you like renting with this particular company and how you’ve been planning your dream vacation for months. Then ask: “Do you have anything exciting today?” It doesn’t always work (and it’s useless to try it over the phone with a reservations agent), but results can be magical, like the time I scored a Mitsubishi Eclipse Spyder in Phoenix, just because someone felt like being nice.

3. Forget city rentals

Not only will renting downtown double the price (somebody’s got to get those cars back into town), but reservations don’t always guarantee a car on busy summer or leaf-peeping weekends. Once in the middle of July, I waited for 90 minutes on Sutter Street, in San Francisco, to get to the counter, picking up bits of every foreign language on earth as I crawled through the line. It would have been easier—and cheaper—to take the BART subway down to the airport. And I’d have been halfway to Monterey already.

4. Add-on costs are not a joke

Take the insurance, for example. Please take the insurance. Or at least know some details of the ins and outs of coverage. “Many people don’t realize that, yes, most premium credit cards cover rental liability for damage, but only after their own insurance has kicked in,” says Joe Brancatelli, who produces the online newsletter, Joe Sent Me, for business travelers. (If you don’t own a car, then the credit-card company does indeed become your primary insurer.) With the collision damage waiver (CDW) now an extra $15-$25 a day, it’s up to you to decide whether it’s worth the charge or if you’d rather deal with an extra hit in premiums from your own insurance company in the event of an accident. I take the CDW for peace of mind; Joe thinks that’s crazy. (P.S. In some states, like New York, it’s illegal for rental car companies to charge for CDW.)

5. America owns the road trip

Renting overseas is complicated and expensive—not only for the cars themselves but also for gas, which in Europe costs at least twice as much as it does here. (In some countries, notably Italy, Ireland, and Spain, laws require you to take the CDW, too.) Why bother, especially in much of Asia and in Europe, where the rail systems are so good? In countries where driving is on the left—Britain, Ireland, Japan, Australia, and the Caribbean—ask yourself if you would you be comfortable terrorizing an entire population. And beware of standard transmission, much more common overseas. I know a travel agent whose American client insisted on the cheapest car for a drive along the notoriously windy Amalfi Coast even though my friend warned his client that it would mean a stick shift. The client returned and sued on the grounds that he hadn’t been sufficiently warned how frightening the trip would be in a car without automatic transmission. (The judge threw the case out.)