IF BY AIR...
Don't bring what you don't need. Do the math with your particular airline and decide which is cheaper, checking a bag or stuffing everything into a carry-on (it varies widely these days). Then, pile everything out on the bed by priority and fill your chosen bag until you can't fill no' mo. (FYI: After being raised on the flat folding method and resisting the conversion for years, I am now a roller. I believe in it. Try both and see what you like.)
- Underwear: enough for four days. Wash in the sink using the hotel shampoo when necessary.
- PJs: pack something lightweight in case the room is hot, throw in a thin sweatshirt or use a sweater in case it's cold.
- Overcoat: use something that can do double-duty as a robe, extra layer in bed, or indoor layer if possible. If you need a dressy coat, wear it on the plane.
- Shoes: something comfortable enough for casual to moderate walking that will also be acceptable for professional dress + one "sporty" pair (running shoes or active sandals) for higher-level activity. Despite the tedium of security, consider wearing the biggest shoes you plan to bring, like boots.
- Toiletries: Think ahead and hoard hotel shampoos, conditioners, and lotions for any trips where you will NOT be staying at a hotel later. Pack them now if you are staying at an actual person's house so you're not mooching any more than necessary off of them. A contact lens case works great for small amounts of BB cream, foundation, face of eye cream. And use multitaskers whenever possible: Body Shop Coconut Oil Hair Shine is my hair cream, my body lotion, and my lip balm.
- If you read, use the smallest device you can still stand to read from. tablet --> Kindle --> phone.
- I always throw in one small notebook and a pen to scratch out ideas. The randomness of sitting in an airport or on a plane for a long period of time allows the mind to wander to some pretty weird, wonderful places sometimes.
- Load up your phone with helpful travel apps (see below), addresses, and music. This can be your portable office, music player, GPS, alarm clock, phone...don't bring extra stuff to perform any tasks your phone can do.
- Food stuffs: I always throw in a spoon, some instant oatmeal packets, instant coffee, and a bag of nuts so that I don't let my hunger get the best of me when there's no decent food around. Tea bags and Emergen'C are pretty obvious on this list, too.
- Neti pot: if you ever use one, bring it. Get one of those plastic ones from Rite-Aid that you can't easily break. If you start feeling a little under-the-weather or are getting really dried out from your hotel room, this will stave off a full-blown cold. I promise.
- Ear plugs. Do not leave without ear plugs.
IF BY LAND...
It is luxurious to have a back seat to throw in some extra things, but it sucks to make ten trips to unload and load the car, especially if you are also fumbling with your hotel key to get into the side door each time. Don't be a piggy, but I like to add:
- Extra shoes, coat, sweaters; add one bag of bulky stuff you might like to wear.
- My very own pillow. Ah, so luxurious to not wake up with a stiff neck.
- A bowl and a mug for my instant food stuffs, listed above
- Fruit. Mmmmm, fiber.
- A screw-cap bottle of wine. Because. Shut up.
Planning ahead with travel websites...
bing.com/travel: Helpful for hotel and plane tickets, this site's "price predictor" has never steered me wrong (when available), and you can sign up for alerts on prices, too. kayak.com will also give you alerts.
cheapoair.com, however, sometimes has cheaper deals, so once bing tells you to buy, look there, too. And check the home websites for any airline you're considering. You will sometimes get the best deal from them (or in the case of Southwest, the only deal).
hipmunk.com: if you're ever lucky enough to go someplace where train is also an option, hipmunk will analyze ways to get to your destination (well, only plane vs. train) by price, duration, departure or arrival time, and level of "agony" (things like multiple connections, pricey tickets, etc.). The agony part is funny to me.
travelocity.com: this seems to yield the most competitive results and the best overall prices for rental cars for me, hands down, every time.
Travel Apps I like:
Gas Buddy: helps you find the cheapest gas in your location.
Hotels.com: I use this one because I have an account with them. You can make reservations on-the-fly when you see what town you've ended up in the for the night and each reservation counts towards a free night (plus, hotels.com often has lower prices than the ones posted on the vacancy sign outside the establishment in question).
FlightAware Flight Tracker: Track your flight, look up other flights in the vicinity to help airport personnel get you on the right flight when you've missed your connection, and get updates on flight status.
In two weeks: surviving the airport, just in time for Thanksgiving!