1. For packing, the trick is BIT: buy it there.
Pack the minimum you think you’ll need and if you forget something, buy it there. Often I don’t end up buying anything, but making this a part of my trip planning helps me relax and pack light.
2. Passport, wallet, housekey, phone & charger.
That’s my checklist when I leave the house on the way to a flight. Anything else is a non vital item I figure I can take care of when I get there. You could buy a new phone charger there but this is such an oft-forgotten item that you want it on your checklist lest you find yourself drowning in $30 wall warts. If you take heart medication you might want to add that to your checklist. If you DO forget your phone charger, ask the hotel. They usually have a shoebox full of forgotten chargers behind the front desk and will let you take your pick.
3. They’re popular among frequent flyers, but I avoid the Bose noise-canceling headphones because they’re too big (and the travel case makes them even bigger).
You can get a pair of in-ear noise-isolating headphones that are just as good, half the price, and 1/50th the volume (that’s volume in cm**3, not db). Slip them in your pocket and travel light. I use a pair from Shure and they’re fine.
4. Luggage with a lifetime guarantee is worth the slight premium in price.
Briggs and Riley make a very sturdy bag that’s strong enough you can sit on it during a long pre-boarding wait, and with zippers that rarely break. And when they do – in 5 or 10 years – replacement is free.
5. If you’re tall or otherwise picky about airplane seats, use seatguru.com to understand the seat layout of your flight.
Seatguru will warn you about equipment boxes under the seat in front of you, cold seats, or seats with a lot of bathroom traffic.
6. From my wife, I learned to *always* ask for a better price or a free upgrade on hotel check-in.
We stayed 10 nights in a $2400/night hotel room with an in-room infinity-edged swimming pool at Jade Mountain in St. Lucia (it’s amazing, check the website) for less than $300 a night because the lady who checked us in shrugged and said “sure” when we asked for a free upgrade. If they say no, no harm done. And you’ll be surprised how often things are negotiable (I was).
7. For overnight flights, don’t take the sleeping pill until the airplane is actually off the ground.
I once had an 11pm redeye with a post-boarding, pre-takeoff equipment problem that was announced moments after I swallowed a pill. Deboard, wait 3 hours, and finally reboard while fighting off the somnolence. Obviously doesn’t apply if you don’t take sleeping pills to fly (good for you).
8. Never drink on a redeye; you’ll be desiccated enough when you land without any help from alcohol or any other diuretic.
I avoid caffeine for the same reason.
If you travel a lot internationally, it might be worth it to pay the $65/month for AT&T’s international unlimited data plan. It really is unlimited, and as far as I know it’s unique in the world. People from other countries are incredibly jealous that this plan is available to Americans (or people with a US credit history and address).
9. Hotels make bank on the extras: room service, internet, parking, minibar, laundry. Make every effort to avoid these.
If you’re traveling light and need laundry done, find a wash-dry-fold nearby; you can often pay them a rush fee for next-day service (sometimes it’s not advertised) and save a bundle. Take an AirPort Express to share the internet cost with your spouse (or tether through your phone with unlimited international data). Grab a few snacks at a grocery store on the way from the airport to eliminate the risk of eating late-night hunger with $12 cashews.