As our family gets more plugged in, we travel with a virtual Best Buy full of electronics. The kids have media players, I have a laptop, the wife has a Kindle or a Nook, and we usually have an iPad or tablet (or two) for movies. Then we have a camera bag and video camera and a few lenses. Now we also have two DS consoles, one for each youngling, and it's actually getting ridiculous.
Traveling with all this junk is getting rough, so here are some tips I've formulated to help keep that gear safe on the road.
First, always lock up your gear. Leaving the room for an hour or the day? Pop the laptop and other unneeded stuff into the hotel room safe. I usually keep almost everything in there, including my mice and other small accessories. I'd rather err on the side of caution. It also helps keep my cables in one place, even if it's a rat's nest balled up in the back of the safe. This is less about protecting the gadgets from theft than keeping everything in one place.
As a corollary, I'd recommend checking and re-checking that tiny safe before you leave. Many of these have a small fabric pad inside that tends to slip slightly and then you end up with smaller items like memory cards sliding under the pad.
Also consider signing up for hardware insurance. Safeware is the oldest and most popular hardware insurance service (although there is a $200 deductible on gear taken out of the country). You will have to buy a policy for each item in your bag, which makes this a bit pricey. You should also check with your credit card company to see what they cover, as well. Many cards offer theft protection on purchases, but make sure you have your serial numbers handy.
So that takes care of theft. But how do you protect your fancy laptop when you hit the beach? First, put a case on everything. Get a soft rubber sleeve for your laptop and invest in a good case for your iPad. I'd recommend something like the SmartShell Case from Speck, a back panel for your iPad that is compatible with Apple's own Smart Cover. At $35 it's a bit pricey, but it works quite well and protects the iPad's metal back. I'd also recommend cases for the various DSes, PSPs, and iPods Touch that kids will probably be schlepping to the pool.
Speaking of the pool, I'd also recommend trying a Drycase pouch. This case keeps sand and water out of your iPad's ports and allows you to grab your e-reader and flip a few pages even after a dip.
Finally, never, ever check electronics on a flight. I've heard -- and experienced -- too many horror stories about laptops being stolen or broken by nosy TSA officials, and chargers and cables in checked bags could fall out on inspection. As hard as it is to schlep all your gear in carry-ons, getting to your destination with your gadgets intact is its own reward.
Then again, maybe taking the laptop and all that gear on vacation is kind of missing the point. Maybe what we really need to keep our gear safe is to leave it all at home.