I do a lot of travelling. Conferences, /dev/fort, and random trips to the Arctic Circle all factor in, and of course moving to the USA recently means I'm often going back to London to see my boyfriend and my family.
I wasn't always a 'regular traveller'; back in the mid-2000s an occasional summer holiday was the highlight of my travel, and I'd never left Europe. However, an invitation to DjangoCon 2008 changed all that, and now I travel... quite a bit.
I want to share a few tips and observations I've made over the years; hopefully you might find them useful or interesting.
Checklists
Over the years, I've forgotten all manner of things; the first time I went to the USA I forgot my phone charger (and this was back when that didn't mean micro-USB, but a special Nokia one), and more recently I managed to go back to the UK to renew my pilot's license - while forgetting to take said pilot's license.
So, as I forget things and streamline what I travel with, I've built up a checklist, which I've uploaded for you to read. It's a simple thing to run through as you pack or as you leave, and it stops me worrying about forgetting something quite as much (though I still do occasionally).
If you get stressed about forgetting things or prepping for travel, I highly recommend making one! It makes packing the night before (or that morning!) a lot easier and quicker.
Plane seats
There's a fine art to picking a plane seat. As someone who doesn't get up a lot, I always opt for a window seat, and if I can, a window seat on the non-sunny side of the plane (or with the better approach view - for example, coming into SFO, the left side is usually better).
If you're shorter than average, then rejoice, as plane seating is one place you can reap rewards! If you're tall, then I feel your pain, but remember that you generally get the better deal, so you can probably put up with a few hours of your knees being scraped. Exit row seats are, of course, better - as are front row seats, but beware of ones with very close bulkheads and less stretch room.
If you're in a two-aisled (3-4-3) plane, always consider the very central seats over the middle or aisle seats on the side; there's one less person to push past you in both cases.
Finally, the rear seats in a section can be pretty good too; no guilt about reclining (though they may not recline as much), and you can store things under your own seat as well as the one in front. Obviously, all of these things can be checked on one of the seatmap review sites.
Sleeping on planes
If you're lucky enough to be able to sleep on planes, then overnight flights are amazing - I get them whenever I can. It's like teleporting somewhere else while you're sleeping (and you're more likely to sleep if it's nighttime).
To help me sleep, I do a couple of things - make myself tired the day before, and take an inflatable pillow in my small carry-on bag (I have a TravelRest - the odd shape is actually quite good).
Making myself tired is also my general solution to jet lag - you can stay up longer than you should, but it's very hard to go to bed early. I generally get up extra early the day before, sleep a bit on the plane, then stay awake and go to bed about 2 hours before my normal bedtime. This only works, however, if there's a big enough time gap for you to sleep a bit on the plane (intercontinental flights).
Frequent flyer programmes
They're probably not really worth it unless you travel a whole lot, but if you do, then the ancillary benefits can be good. Obviously, pick a home airline and alliance and stick with it if you can; you can find much more detailed advice about which one to pick and what bonuses to prioritise online.
Lounges might seem like a fantastic thing (they did to me), but they're often actually busier than the main terminal, so the only real advantage is free drinks and snacks. If you just want a quiet place to sit, most terminals have empty gates that have just that.
If the lounge charges for even snack food (I'm looking at you, American Airlines), then I often get more substantial food outside the lounge. If you're ever in the LAX international terminal, just go to the Umami Burger there. It's one of the few good things about LAX!
Don't count on getting many free upgrades; they happen very rarely, and unless you're travelling a lot you're unlikely to be very high on the seniority list. That said, when they happen, they're a wonderful surprise (generally, you'll find out at the gate as you're boarding, if they're genuine operational ones).
Spending air miles/Avios/etc on upgrades is the most efficient way to do it, but availability is very limited; Award Nexus is a great resource to check this stuff in bulk.
Power
Almost every device I own has a switched-mode power supply, so voltage is never really an issue these days; just the plug shape. I usually carry two plug adapters and, if I have one, a USB charger with a native plug.
The large majority of my stuff charges over USB; you can even buy USB charging cables for some things that use 5V but aren't USB by default (like the 3DS).
You can never have too many USB cables; I travel with about 4 or 5 usually, sometimes more, which occasionally causes the security people to get quizzical about what exactly is in my bag (but they're fine once they see what it is).
Money & Passport
Unless you have a crazy bank, or you're going to a country without ATMs, just get money at an ATM in the destination airport. It's cheaper than any airport currency exchange shop, and a lot less hassle than getting money via post.
Be wary of third-party ATMs that charge huge fees though; these aren't a good deal. They're usually quite easy to spot - smaller, free-standing, dodgy graphic design.
If you lose your passport, it's not the end of the world - your country will have a consular presence who can get you back home, but it'll take time and money. If, however, you're like me and are living on a visa in another country, it can be pretty catastrophic. Keep your passport and money either on your person or in the hotel room safe (the safe isn't that secure, but weigh it against bag-snatching and other street crime).
Finally, check up on admission criteria for countries before you go! Even if you don't need a visa, several countries (the USA, Australia as two examples) need you to register online before you travel. For UK citizens, the FCO have great travel advice for every country including admission criteria and common crimes/scams. Hilariously, every country is marked as having at least a low risk from terrorism, even Antarctica.
Hand luggage
Travelling with only hand luggage is a wonderful thing. You save a good 20 minutes when you arrive at the destination airport (not only do you skip waiting for your checked bags, you're often skipping the line that forms at customs too), and while some customs agents will stop you and ask where the rest of your bags are, there's never any actual issues (I imagine a lot of people just forget).
My normal luggage
If you do this, though, be aware that you'll need to be at the gate when it opens; space in the overhead lockers is rare on domestic flights, but as the flight gets longer and international the space frees up. Still, you don't want to get your bag checked in the hold for the flight if you can avoid it; it's unlikely to be as tough and secure as normal checked luggage.
Don't buy a hard-shelled bag that's exactly the size limit; it probably won't fit well and you'll annoy everyone. A decent-sized backpack is easier to carry, easier to organize things in, and fits the shape of the lockers better.
I've had great experiences with SwissGear backpacks (in particular, my Blue Ibex one has now lasted about 5 years and is still going strong with nothing broken or worn.)
Finally, the Eagle Creek compression sacs help me squeeze a little extra space out of my hand luggage; they'll reduce the volume of fresh clothes by a little, but they really come into their own for reducing the size of worn clothes. Just put stuff in them, roll out the air, and it's smaller - plus, the clothes are now a single item, making repacking and security checks much less hassle.
Here's a picture of how I packed when going to Australia for a camping trip (yep, that all fits in the two bags pictured above). Compression sacs do a particularly great job on things like sleeping bags.
Packing for Australia
Plane/Train entertainment
Plane entertainment systems are getting better (I even saw one with capacative touchscreens recently), but I never rely on it - and besides, I might have a long train trip too (or, heaven forbid, a long coach trip).
Podcasts are my mainstay here; you can listen to them walking thorugh the airport, waiting in line, during takeoff and landing (more countries are allowing this now), while you're eating food, and all other situations where staring at a screen isn't easy or sensible.
My particular favourites are 99% Invisible, Still Untitled: The Adam Savage Project and Answer Me This! (see if you can find the episode featuring my question). Plus, if you're into games at all, you should be basking in the idiotic glory of the Giant Bombcast.
After that, I have both a tablet (either my iPad Mini or a Nexus 9) and my Surface Pro 3 with me in the smaller bag. Between them, that's about 14 hours of battery life for watching videos - long enough for most flights in the world, especially if you include sleep time. For video content, I have a whole slew of TV shows, YouTube channels and 1980s movies that everyone keeps saying I should see.
I have a Kindle Voyage to read books on, though any eBook reader will do (I've always used Kindles, though). I particularly recommend the works of Mary Roach; she's made many a journey better, and they're easy to dip in and out of as each chapter is quite standalone, though she's made me giggle a little too much.
Finally, a portable games console is really handy, though the iPad mini (and to a lesser extent the Nexus 9) fufills this need too. The 3DS and Vita are both great, though. As with the books, I like games that are either turn-based or have short sessions, but more involved than things like Candy Crush or Crossy Road.
Local Holidays
One thing you should check before you plan anything is what local holidays are on; a surprising number of countries shut things down at random times, and I've been caught out in several places (who knew that all the attractions in Brussels close on Monday, or that apparently every German shop closes on Sundays?)
School holidays will also factor into fare prices; you'll want to check the dates for both your origin and your destination (they can differ wildly). The UK has a particularly fun scheme of week-long holidays halfway through terms that vary by county, so it can become almost pot luck (on the plus side, the effect is lessened).
I've rarely had an issue with children on planes, though; most are surprisingly well-behaved, though I suspect this is because I do a lot more long international flights than short domestic ones.
Wikitravel can be a good resource for finding out local knowledge like holidays, as well as how to get to/from the airport without taking a taxi (I try and avoid taxis where I can).
Trains
If you have the option, and the time (though sometimes they're faster than flying in Europe), trains are great. And, if you want great train advice, you need only go to Seat 61. It's a great resource for train travel basically everywhere.
I have particularly fond memories of the Caledonian Sleeper (London - Scotland) and the Paris - Bourg (French Alps) sleeper. It helps that both of these end up in cold, beautiful places - my favourite kind of place.
If you're unfamiliar with trains (i.e. you're American), Seat 61 has good guides as to how the ticketing system works in most countries. Booking early can offer you a significant discount, as can rail passes (especially in Europe and Japan).
The Go Bag
The final piece of advice I have is that it can be very convenient to have two of everything you need to pack so you can leave things semi-packed and ready to go.
For example, I have a separate set of toiletries and toothbrush for my travel bag; I top up the mouthwash from a big bottle every now and again but for the most part it just waits for me to grab it and go (and there's a few changes, like a stick deodorant rather than a liquid or aerosol one).
The cables and adapters that live in the bag, similarly, are duplicates of the ones I have round the house. I even have a second laptop/Surface charger just for travelling so there's no need to spend 5 minutes untangling mine from the desk.
Some of these things are cheap to buy multiples of (like toiletries), others are more expensive - it's your call what makes sense. It does mean, though, that packing for me basically just consists of clothes and laptop; pretty much everything else is always ready to go.
Conclusions
If there's two important things I think you should look into, it's checklists and compression sacs - they're the two things that changed my travelling experience the most. You should also take more trains - I really miss them as an option now I live in the US.
A lot of the rest of it is experience - learning how to escape Heathrow quickly, or how close you can turn up to your departure time at SFO, to realising that you really can just get a flight to anywhere, hire a car there, and drive somewhere.
My hope, one day, is to cross off every single one of the destinations on my Places To See list, but until then, I have checklists to refine!