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This page will definitely be a work in progress, but every time we hit the road, we learn something new about the advantages of what we chose. Or its shortcomings.
1. Keeping It Light Enough For Ryan Air & The Air New Zealand Luggage Zealots in Queenstown. Some of the carry-on limits for airlines outside the USA are incredibly restrictive. 7 kilos, and I've had that enforced in biz and first as well. The purported safety reasons are preposterous, but they are what they are, and if you attempt to defy them, you do so at your peril. So, what do you do, especially if you are on a once-in-a-lifetime trip to Africa, or New Zealand, or Iceland, or Bali and hauling that monster 800mm lens?
2. If you've got to check something. Cut the amount of clothes in your carry-on down to a set of underwear. In the colder months, wear your heaviest layers on to the plane, so they're not taking up room and weight allowance in either your carry-on or checked luggage.
Although most luggage—the vast majority, gets where it's supposed to go—remember it is likely to get opened up by people who "admire" your gear. So, try not to place any camera equipment of value in your checked baggage. Anything more valuable than a tripod is, not surprisingly, asking for disappointment.
But if you have no choice but to check camera gear, don't try to disguise it and don't skimp on the container. Put it in a piece of luggage designed to protect it like a Pelican. Skip the nuclear orange and lime color combo I once had and go with some version of gray or black. I had a theory that no one would try to make off with something so obvious, and I may have been right. But it also got my pulled over for extended inspection every single time [domestic TSA and foreign equivalents are not rocket scientists; they apparently think that bad guys advertise what they are doing]. Before you check your luggage, open it up at the airport and photograph the contents; that way, you will have a time-stamped photo of your ownership. Also, make sure you have receipts for your equipment with you. If those are not available, take individual time-stamped photos of each piece of equipment you own or rent, preferably at least a week before travel, and print them out to have with you. This will help deal with aggressive customs officers.
3. Make sure to insure your equipment. This is such a no-brainer, but it bears repeating. Don't just insure yourself and your trip; insure the equipment. I use insuremyequipment.com, and I also get free coverage through my membership with NANPA. There are plenty of option, and it's not expensive. I went swimming with my equipmentonce and learned this lesson the hard way. Don't make that mistake.
4. Traveling by car. Now you're cooking with gas. So to speak. You've got almost unlimited capacity to carry whatever you want. That is, until you have to put it on your back and carry it somewhere. Think it through. The car or van or whatever is great for making sure you've got a closetful of gear and accessories and every "what if" lens you could imagine. But all that equipment can cause far more problems than it solves. There is nothing like arriving at a brand new place, feeling overwhelmed by its awesomeness, and getting paralyzed by the breadth of your equipment and being unable to visualize your image.