I am by far no expert but I have spent the better part of the past two years on the road as a musician in Canada, doing about 5 tours, coast to coast.
The following is a response to a post on http://www.the905board.com , asking about touring.
Heres my perspective:

1. Figure out why you want to tour (New album promotion, fan demand in a city, personal enjoyment, the sense that hitting the road sounds cool, you really wanna learn how to tell your band mates apart solely based on the way there ass smells etc.)
Seriously though, define what you want to get out of being on the road and be honest. Are we ready? Can we all handle being together cooped up in the van? Can we afford it? Do we have merch?
It’ll make for far less resentment at the end of the tour. If you think you’re gonna be HUGE cause you’re hitting the road, then I hope you’re Stereos or something the girlies get all tingly for. It’s hard to do it successfully, but touring is by far the most enjoyable way to see any country and meet people. If you do it right, you can even pay your rent at the end of the day.
2. Find out when and in what cities you want to play in or should play in based on #1 and route your tour.
With a little help from Google Maps, you can find out how far each city is from the other. Isn’t technology grand?! Using that info you can find out how many KMs you will travel and THEN find out how much gas you will need to have to get you all home to your GFs. Granted you still have them at the end of the trip.
3a. Now that you know why you’re going and roughly how much its gonna cost to go, begin contacting other bands in your genre (Girlie Pop Punk, Uber Cat Stomping Death Metal Shred-Core) in those cities and set up / swap shows. Swaps are by far the best way IMO.
Swaps are great cause you meet other artists and acts trying to do the same thing you are. Plus you get an empathetic ear when you’re in Vancouver and want half your crew dead cause they ate the one thing you bought but your Vancouver buddies talked you out of slaughtering them for the betterment of the tour.
3b. Search the cities you want to play in on Facebook and Google Searches to find SCENE Hubs*. (Ex Search: “Hamilton Music, Hamilton Music Scene, Hamilton Shows”) People make Facebook groups for EVERYTHING, I’ve lucked out by just doing this to find contacts and set up shows.
*SCENE Hubs are places online where show goers’, promoters and music lovers hangout, chat about shows, bands and /or music in general for a specific market. More often than not if you post about wanting to play and are willing to swap in your hometown, don’t suck, and aren’t douchey you’ll get some interest. Ex. http://www.stilleposte.ca | http://www.royalcitymusic.ca | http://www.overhear.com These sites are constantly changing and new ones are popping up.
4. Now you’ve touched base with a bunch of bands, set up a YMCA show here a bar gig there and a house party gig at your Moms friends daughters place. Remember when your Mom sent your CD to all her friends cause she was so proud of her little mans first demo, well now her friends hot daughter wants you to play her 18th birthday. Did I mention all her friends are hot and think you guys are the cats meow too? Bingo bango.
But shit, the house party dates conflict with another show in Windsor that pays better. Time for tough decisions and finalizing bookings.
5. Dates are now locked down, start contacting any press be it local or college radio, any music bloggers, post the show in the SCENE Hub forums and Facebook pages (according to their rules of course. People like Hermit exist everywhere…and he’s the nicest) to let people know you are coming.
A nice, short press release that can lead to more info about the tour on your website and of course your music link (http://www.myspace.com/thefold) is usually all you need depending who you are sending the release too and your current level of success.
Your music is by far the most impactful impression. If I log onto your MySpace and your music rocks but your pic isn’t the BEST, to me it’s not a big deal, but these days if you can’t get someone to give your MySpace a spruce up and a friend in photography with a nice digital SLR to snap a pic of your band…I dunno. Chances are if two bands are vying for the same night, but their page looks more pro and the music’s on an even keel, I’ll take the guys who took the time to look professional. I figure they won’t give me a hard time. Not always the best thing, but the reality.
6. Alright, shows are booked, you’ve contacted a bunch of bands, set up show swaps, done some press, sent your CD out for reviews, got all your new online friends you’ve met hanging out in the music forums coming to check you out, got your video camera to make blogs on the road, got any contracts worked out and printed off copies so if Mc Douche promoter tries to not pay you the $100 he said he would, you can jog his memory with a copy of the email he sent.
I prefer to advance shows twice depending on how long in advanced I have booked them, but calling the venue a few days before your gig to ensure the night is still on, the venue hasn’t burned down or the promoter hasn’t been fired is a good rule of thumb.
7. Pile in your van, kiss your Mom, GF/BF, pony, pet lizard, financial security, day job, friends, your local bar, sanity and ego goodbye. You son, are on tour.
Note: This is a really quick overview, if you disagree or have something to add, please do.