As Brian Owens was getting ready to head out to dinner with his wife and some friends on a trip to Germany, he couldn’t resist trying to surreptitiously e-mail a client back in the U.S. With his wife in the next room of their hotel suite, he says he set his modem to auto redial, then left. Owens, senior vice president of operations and strategy at Fieldglass Inc., a software maker (www.fieldglass.com), returned four hours later to find that his computer had continued to dial and redial and redial again without ever managing to send the e-mail. When he and his wife checked out, he saw that he had been billed $8 every time the phone dialed. The phone tab came to $1,450.

“Don’t leave home without it” used to be an advertising line. Now it’s becoming a mandate for many vacationing executives, who stuff their luggage not only with sunblock lotion and bathing suits but also with cellphones, computers, and personal digital assistants. A recent American Management Association survey revealed that 68% of executives planned to contact the office while on vacation; 25% said they would make contact by phone or modem every day.

The trend may be inevitable, but many executives, like Owens, find that it is introducing a new level of complication into what is designed to be a relaxing time.

Owens, a technology recidivist, says that, even though his wife still razzes him about his $1,450 phone bill, he later attempted to smuggle his laptop on a backpacking trip they were taking through Italy. His wife discovered it after he tried to check it for safekeeping at the front desk of a small hotel. She was not amused. (An observer might have been: Owens had forgotten to pack the power cord, and the battery was dead, turning the laptop into useless weight.) “The laptop survived the trip,” Owens says, “but without Venice—with its romantic canals—I’m not sure I would have.”

When attorney Stephen Cunningham joined a friend for a two-week sail in the Caribbean, the pal arranged at great expense to have the boat outfitted with a satellite system so that Cunningham could stay in contact with the office. “Of course, it didn’t work,” Cunningham says. “Instead it sat there for two weeks as a reminder of ambitions gone awry.”

A consultant, who asked not to be identified, said she was surprised to find that there was just one phone line in a vacation cabin in the woods. She and her husband had so many conference calls during their holiday week that they had to set up a sign-up sheet by the phone to reserve blocks of time. Because cellular service was spotty, when both had to be on the phone at the same time one of them had to walk half a mile up the road to be able to make a cellphone call.

An executive, who most definitely does not want to be identified, tells of booking a getaway in Hilton Head, S.C., with his wife. But—in an episode like something out of a Steve Martin movie—he wound up having to make a presentation to clients during a four-hour conference call from hell. Here’s what happened:

With his laptop hooked up to the only phone line in the condominium because he needed access to some materials online, he used his cellphone to talk to the client. But a heat wave caused a power outage in his unit. His laptop battery soon ran out of juice, and his presentation materials vanished. Next, his cellphone reception began to break up. With the condo approaching 100 degrees, he ran outside to find better reception. He found it in the middle of a baking asphalt parking lot. There he stood in the blazing sun, ad-libbing his presentation—until his cellphone began beeping a low-battery warning. He ran back inside to grab his power adapter. But where was a working power outlet? After a frantic search, he found one in a poolside locker room. Dripping with sweat, he finished the call while, around him, other male vacationers noisily used the bathroom and took showers.

Headhunter Eileen Goode says that when she and her family drove to Wisconsin from Boulder, Colo., for vacation this summer her five-year-old daughter enjoyed watching digital movies on Goode’s laptop computer during the 18-hour trip. But staying in touch with the office brought a message that ruined the vacation. While compulsively checking e-mail, Goode’s husband found out he’d been laid off by the Internet start-up where he worked. Goode spent the remainder of the holiday conducting an online job search for her mate.

WorldCom Inc. (www.worldcom.com) public-relations executive Debbie Caplan thinks the “fantasy of being completely disconnected” isn’t worth the “anxiety of not being able to connect at all.” But that doesn’t mean she hasn’t faced anxiety staying connected. Arriving at a quaint beachfront motel on the New Jersey shore for a weekend getaway, she discovered that its old-fashioned phones were hardwired and that she couldn’t plug in her laptop. “I was so determined to connect that I found myself on the floor, using a knife to unscrew the wall plate to see if there was a way for me to plug in,” Caplan says. On her hands and knees, peering at a tangle of old wires, she came to the realization that she’d just have to communicate the same way her grandmother had—by talking on the telephone.

Still, some executives seem to be able to smoothly integrate office technology with their vacations.

Neil Verplank, founder of Dovetail Information Design (www.dove-tail.com), often takes his laptop and a solar panel along on back-country vacations so he can work out of a tent. He says that works just fine.

Andrew Lippman, a founding member of the MIT Media Lab (www.media.mit.edu), says he has learned to take precautions about bringing electronic equipment along—but only because the avid sailor has accidentally dropped several cellphones overboard. He now routinely brings four cellphones (an analog, a digital, and one for each of two satellite systems), and three laptops on voyages.

“The bottom line is that there is no excuse to be offline should you wish to remain in touch. I would never be able to sail as much if I had to disconnect myself from the entire world when doing it,” says Lippman, who cruises mostly off the coast of Maine but also finds himself in such far-flung spots as the Southern Ocean.

Andy Birol, a Cleveland-based business consultant, asserts that technology lets him take more vacations than he could otherwise, because being out of the office doesn’t mean he’s leaving anyone stranded. Speaking from his cellphone while sitting by a hotel pool in Branson, Mo., Birol says he conducts business only while his family swims or watches videos in the hotel room. “I am extraordinarily family-oriented,” he says.

“I’m sure there’s some guy across the pool saying, ‘Who’s the idiot with the cellphone on his ear?’” Birol says. But “if that person is on his one-and-only vacation this year, then who’s the idiot?”