How I Travel

Over the years, I've made many a travel mistake that resulted in many less-than-pleasant experiences.  Below are a few things I do to make every trip as enjoyable as possible.

Check My Bag
I'm usually on international flights so checked baggage is free, but I find the world seems brighter after obnoxious rolling suitcase has been taken away.  No navigating through crowds with a trailer, no tripping on the wheels, no carrying it up stairs, no cramming it into the overhead compartment, etc.  Unless you're rushed upon arrival, get rid of the bags.

Carry-On
I try to keep this down to essentials.  Have a folder for travel documents, an easy-access (but somewhat secure) pocket for passport and boarding pass, a notepad, pen and pencil, tissues, a good pair of on-ear headphones with airline converter (two prongs), and light jacket for the plane or to use as a pillow if I need to sleep on a bench or floor.  For entertainment, I love travel magazines or novels set in my destination.  The airport experience is quick to suck all idealism out of travel and I like to arrive feeling romantic.  Years ago, I remember watching the "Vietnam" episode of Anthony Bordain: No Reservations when he mentioned that his motivation for vising the country was Graham Greene's The Quiet American.  Since then, I've always followed suit.
The 21st century has been kind to travelers, providing smartphones and tablets that can be packed full of reading material, movies, music and games catered to you.  Airline entertainment can be wildly irregular so it's still best to have your own stuff.  Also, I always have a toothbrush and travel toothpaste for when I get off the plane.  For me, patience and a clean mouth go hand in hand.

Dress for Comfort and Airport Security
Avoid all jewelry and accessories when flying or pack everything in your carry on before you get in line at security.  It drives people crazy when they have to wait for someone to strip down at the front or remove watches and wallets to walk through metal detectors a second and third time.  I'll always wear a sturdy pair of comfortable shoes that can be worn in any situation and are easy to get on and off such as modern lace-free Royal Elastics or desert boots.  Have your computer or tablet out and ready to put into a separate box and your boarding pass and passport in your hand.  When I get through, I'll buy a bottle of water for the plane.

On the Plane
It's nice to spend your hours of free time preparing to customs and immigration.  I'll always use my own pen to fill out cards beforehand rather than use the cheap 3 inch pencils at the tiny desks in the airport.  I'll sleep as much as possible if I'm flying east, but try to stay awake if I'm flying west and avoid alcohol completely.  It's free, I know, but it's not worth arriving feeling sick or buzzed.

Souvenirs 
For the most part, I've completely stopped buying souvenirs for myself.  Living in Japan, I'm required to buy huge quantities of sweets everywhere I go for students, friends, and coworkers so I need any extra space for that.  For my family, I like to find authentic local art or crafts that can only be found abroad.  Cheap t-shirts and trinkets may seem like a good idea at the time, but they add up quickly and don't last forever.  As a keepsake, however, I have always taken a coaster from every city or country I visit.  They're small, light, free, and unique.

Eating
I always try to avoid big restaurants.  The English may be better, but they're usually overly tourist-friendly dishes that may lose some local flair.  I love to buy from street carts or hole in the wall places with grandma cooking in the back, mom and pop working the register and taking orders, and the kids serving drinks.  The food is authentic, the ingredients are local, and the experience is richer.

Planning
I prefer to avoid tourist guides and read travel blogs and chat rooms for tips.  I'll never read user comments in any other situation, but travel sites have some good stuff in the comments.  Just find a post about "the greatest _______ in _______" and take advantage of the debate that follows.  I'll finish with a long list of local places to visit and tourist traps to avoid.