Back in the Dark Ages — which, for me, was in the early 1970s — staying in touch with family, friends, and business colleagues while traveling abroad was a relatively straightforward affair: it simply didn’t happen. It was possible to call people on the phone, but there were no discount phone services, so it was outrageously expensive. No fax, no e-mail, no Twitter, no instant-messaging. If “instant” written communication was absolutely necessary, I would resort to telex or telegram. Western Union was actually part of my life back then…

I don’t remember any significant improvements in the 1980s, but by the early 1990s, it was barely possible to communicate via e-mail in most civilized countries around the world. It required a low-speed acoustic coupler/modem, or a phone cord with RJ-11 jacks if you were traveling to a really advanced country. CompuServe was a godsend, because it provided local access numbers in every country that I was likely to visit. And there was a shareware program that interfaced with CompuServe in such a way that you could “batch” your email uploads and downloads, making it possible to send and receive dozens of (text-only!) messages in a matter of a minute or two. This wasn’t necessary to minimize telecommunication charges per se, but rather because CompuServe was charging for its access, by the minute.

Today’s Facebook generation is unaware of all of this, except perhaps for some dim childhood memories of their parents screaming at the telephone while trying to connect their primitive laptop computers (I once lugged a KayPro computer all the way to Australia and back) to the so-called Internet from a hotel room in Rio de Janeiro. Now we’ve got mobile phones that work in both North America and Europe, and we’ve found telecommunication carriers that make it possible to call home and say “hi” to the family for a few minutes, without taking out a second mortgage on our worthless homes. We’ve got WiFi in our hotel rooms, though they’re still pretty expensive in Europe (15 euros a day, in my hotel here in Rome, where this blog is being written).

But ironically, things have actually gotten more complex in the last couple years — so much so, that I’m planning to create a checklist before traveling abroad again, to make sure I haven’t overlooked a few critical things. Why? Well consider what I’ve brought along on this trip to Rome: my Mac PowerBook laptop, my iPhone, a Blackberry, and a brand new iPad. Maybe it’s overkill, and maybe I could have left one or two of the devices at home — but there was a conscious reason for bringing each device along, and the “care and feeding” for each device requires some conscious attention.

For example: why bring a Blackberry? Simple: my T-Mobile carrier has an economical $19.95/month plan for unlimited e-mail activity when out of the country. It’s pro-rated, based on many days you actually need the service, so I simply call T-Mobile and tell them, “Turn on the international service on day X, and turn it off on day Y.” Normally I hate the Blackberry as an email device, because (for reasons not worth explaining in details here), the messages don’t go through my normal “filtering” rules to eliminate spam and garbage mail. But it’s better than paying a king’s ransom to get my email on my iPhone when abroad.

iPhone users might ask: why not connect your iPhone to the Internet via a WiFi hotspot, and avoid ATT charges completely? Well, that’s fine if you have a WiFi connection — but if you’re out on the streets of Rome, or attending a conference in some random hotel in Rome, chances are that you don’t have a WiFi connection. And while ATT does make it possible to use its 3G cellular connection while abroad, it really does cost a fortune — as I discovered after running up $500 in charges with my iPhone during a one-week vacation in the Caribbean a year ago. So the Blackberry, with T-Mobile’s service, is essential for e-mail.

But of course, that means you have to re-route your email from wherever it normally goes, to the Blackberry e-mail address. That’s easy to do, and in my case it requires checking one simple box on a Web page where all of my email preferences are configured. But if you forget to do it, as I did at the beginning of this trip, none of your email gets sent to the Blackberry. It was a minor nuisance, rectified as soon as I checked into my hotel, and connected my laptop to the Internet via the hotel’s (expensive!) WiFi system … but still a nuisance.

Meanwhile, you’ve got to ensure that any email that normally gets sent to your iPhone isn’t going to trigger AT&T’s expensive international charges. That requires turning off “data roaming” (so the iPhone doesn’t try to grab onto whatever local telecommunication carrier it can find in Rome) and also turning off “push” notifications (so that CNN will stop sending me “news flashes” that the oil spill in the Gulf of Mexico is even bigger than it was an hour ago).

That was fairly easy to remember … but now I have to remember to do the same thing on the iPad, too. It operates much the same way as the iPhone, in terms of the data-roaming and “push” options. Fortunately, I remembered that one just before my plane took off from JFK.

And then there’s the mundane stuff: each device has its own AC adaptor/charger, and its own cable to connect to the USB port or the iPhone/iPad port. Each device has its own adaptor for “foreign” (international) power plugs. The laptop and the iPad have different VGA adaptors if you want to plug them into an LCD projector for a presentation.

Oh, and one last annoyance: they all want to connect to the Internet via WiFi. But if you’re in a typical hotel room (either domestic or international) where there’s a per-day charge for accessing the Internet, you’re almost always restricted to a single device. I could understand that if my wife and I each brought our own laptop on a trip, the hotel would want to gouge both of us for the privilege of accessing the Internet. But I’m here by myself — and I want to use my iPad to read the New York Times in the morning, and then use the laptop for sending/receiving email, browsing the Web, and various other things. Or I want to transfer a spreadsheet or Powerpoint file (it’s actually Keynote on the Mac, but that wouldn’t mean anything to Windows users) from my laptop to my iPad; the transfer goes through iTunes and requires a “synch” with both devices connected to the Internet.

All of this is almost more trouble than it’s worth. I sure don’t want to go back to the ugly era of communication via telegram, but I’m beginning to wonder if we were actually better off in the days of low-speed, text-only communication via CompuServe. Unfortunately, CompuServe is just a dim memory. For better or worse, we’re marching into a brave new world with all of our beeping, blinking, more-or-less interconnected devices…