On another one, I was in Jamaica for two week stints more than a dozen times.
This kind of travel can be lonely and exhausting. I've learned a lot about how to do it better, without necessarily having an executive budget.
Cheers to the free agent nation!
Step 1: Packing the Clothing Part
You're going to be humping all this stuff around yourself, so keep it as small as possible.
Even if there is access to laundry facilities, one thing you will not have when traveling on business is any time. But you can do a two week trip out of a rollerbag. Here's how.
 minimize patterns. everything needs to go together
 keep your rattiest undies for traveling. Throw them out as you go. [You can also hand-wash underwear, of course. I use shampoo for this]
 pack things like underwear scarves socks in ziploc bags. You can squish all the air out to get a very compact package and stuff it in the bottom of the bag. After arrival, the ziploc is for laundry that will be repacked.
 save think tissue paper from shopping or whatever. Fold sweaters and shirts around tissue paper. It keeps everything wrinkle free and surprisingly crisp. And there's nothing like putting on a crisp shirt after more than a week in a hotel. (Some people use drycleaning bags for this, i prefer tissue paper)
 roll soft items like sweaters, even those packed in tissue paper.
 get a pair of really cheap canvas sneakers that can crush down, so that you have some sport/casual shoes in addition to business shoes. I usually take some flip-flops so I have something to wear around the hotel also. [It's not like they clean those carpets too often]
Step 2: Packing the Briefcase
So I use a big plastic pipe thing to take flipchart paper with me, unless i am sure i can get it on site. This doubles as the way to carry finished flips back home for processing, if needed. (Better to take digital pics and recycle the paper at the hotel, after the workshop. That is what I usually do.) If you have an empty tube at the end, you can stuff it with anything you acquired on the trip.
I also take anything like post-it notes or felt pens that i might need.
Since you cannot travel with sharp objects anymore, I take this very handy sheet cutter with me. It is small, and you can cut a page from a magazine, or cut a flipchart off a deck quite easily.
Do what you can to keep your computer plugs secure. I once opened a briefcase in an overhead bin on an airplane, left part of the plug behind, and spent precious hours and cab money chasing around to try to get one locally. In a major city!. Better not to lose them.
Roller-bag briefcases sound good, but don't fit under an airline seat, hold less than a regular one, and weigh a ton to lift into the overhead. I have one, but never seem to use it.
Other essentials for the briefcase:
- writing materials. i also carry a few stamps and envelopes (stamps need to be local, of course)
- ipod and headphones
- adapter jack so i can use my own headphones on the airplane
- travel wipes and SHOUT packets, for the inevitable spills
Avoid fountain pens and rollerball pens -- at reduced pressure, they tend to leak.
Step 3: The Hotel
If you know you will be staying in the hotel again, memorize the floor plate. There are often larger rooms, and they tend to end in the same number. This gives you options at check in.
On the Jamaica project, I learned that all the business travellers stayed in one of four hotels in Kingston. I have stayed in all of them. All are nice, but the seasoned veterans always seemed to stay in the same place. I learned why.
One of the hotels had these old low-rise units with balconies. You could see people and hear the action at the bar. The sight and sound of people close by makes it much less lonely, and you never wait for an elevator. I started booking a room in these units whenever possible.
This became my favorite place. There were plugs near the pool area, and on weekend mornings people would go out and move the tables around in order to work on their projects on the laptops. There was one dining room that served a buffet that changed every night. If you didn't have time to go somewhere else, at least you had some variety. And waiting for table service gets old really fast when you just want to eat and get your work done.
The other rule I have is to stay at a place where I can safely walk somewhere. Anywhere. It means you can find some other places to eat, find a good coffee shop, and are generally not trapped in the hotel.
My best tip: tip the chambermaid the first day.
Step 4: Extras If You Have Room in Your Luggage
A small thermos is a nice luxury. You can get the hotel dining room to fill it for you with coffee, and you are set for the day. Or if there is coffee in the room (often the case now), you can fill it yourself.
I take my own selection of tea bags, just a few. Plus some powdered creamer packets. There is often a coffee pot in the room. In a pinch, I recently made a one-person serving of KD in the hotel-room coffee pot (designed to be microwaved, but it worked okay, and I was tired and hungry, and not willing to pay room service prices)
You want your own water on the plane. So either buy a bottle after you go thru security, or take a SIGG bottle that is EMPTY. Then fill it at a fountain.
Small speakers for your walkman/ipod can be nice to have in the hotel room. Or some music on your laptop.
If you are checking your bag, a corkscrew is a nice extra to have with you.
Step 5: Being Local
Go for a walk and find some local eateries. Much cheaper food is often a short walk from the hotel. After several days, or several trips to the same city, you will definitely want other options.
You can order pizza or other take-out in to a hotel. It seems obvious, but it took me a while to figure this out.
Cabs and rental cars are rarely an option for budget reasons. I've found that local buses and commuter trains/subways are great. Cheap, and you get to see the world from local eyes.
Step 6: Finally...
I try to locate the plugs in the airport, and move around the furniture if necessary so I can do a little work while waiting without draining the battery.
Then if I get my work done, I can just crash or watch the movie, a much better option than trying to work. Sometimes it's confidential work. And who knows who is sitting beside you or watching over your shoulder.
Spend the money to call home every day. You're not the only one feeling lonely, so is your spouse /significant other. And send them some meaty e-mails too, telling then what you are up to. Well worth the internet charges.
See you on the road!