I’m not really going to go into the nuts-and-bolts stuff here. There’s plenty of information on which bicycles are good for touring, for example. It’s mostly going to be cheerleading of a sort.
My semi-goofy short answer: Get a close friend or significant other who is into touring and is willing to bring you along.
My not-so-goofy short answer, which is compatible with the above: Do what you can with what you’ve got.
Yes, whatever you have, start with that. If all you have is a three-speed with a basket, find a flat route that leads to a hostel or cabins or a yurt or best of all, a friend or relative’s house. If you have a bicycle that won’t fall apart on you, and find a route you can ride in a day, you can do your first out-and-back overnight trip. Carry a backpack if you have to (try to keep it non-heavy, backpacks are hard on your back when you’re biking). Borrow a trailer and put a duffel bag on it if you have to. Take buses most of the way there if you have to. If you really want to start touring, do what you have to and try it!
Hopefully, when you get back from your first trip, you will be thinking, “Oh, that was nice, but it would have been easier/more fun/more comfortable if I had this/did this…” Don’t think you have to have/do those things to tour again. If after my first trip on the mixte, I’d said to myself, “I’m not doing that again until I have a Surly Long Haul Trucker, and both front and back panniers, and real bike shorts,” it would have been my only trip.
*Be willing to borrow and/or buy used. My first trips were done with borrowed panniers, for instance. Ebay and your local CraigsList are good places to look, and so is a used sporting-goods store. I’ve borrowed a sleeping pad, bike shorts, and on one occasion I almost borrowed a bicycle. Does a friend have a tent you can borrow?
*Be willing to use what you have at first. Don’t have jerseys? (I think they’re over-rated anyway.) Wear t-shirts. I still don’t have any cycling-specific shoes, although I’ve found shoes I like just fine.
*Start small! Maybe go someplace twenty miles away your first time. Then maybe a little farther next time. Your confidence will increase with every longer trip you do.
*Read, read, read. Does your library have books on bicycle touring? Even if they’re old (Shawn owns some from the 1970′s and earlier!), they often have good advice. Find blogs by people who do lots of touring. Sometimes sources of information will disagree, and that’s okay–not everything works for everybody.
*If there’s an email list for cyclists in your town, get on it, and ask about places to go nearby.
*You might try your local bike shop, but be aware that if the people who work there have never done touring, they might not be any help.
*I’m a huge fan of overnight there-and-back trips as a way of starting. You’re never that far from home, and if it sucks it doesn’t suck for very long.
*When you go to buy/beg/borrow things for the trip (a camp stove, a tent, a sleeping bag) look at stuff aimed at backpackers. They, like you, have to carry all their things with them, and so having things that are small and lightweight is a good idea. You can carry more than a backpacker does, though, and isn’t that nice?
I did say that having a significant other or close friend into cycle touring can help. And it really can–if they do it right. That’s how I started touring, after all. If your partner plans your first trip out to be a week long, eighty miles a day, with a few mountain passes thrown in–that’s not so great.
If you are the significant other/friend who is trying to get someone started on touring, I have some words of advice.
*Increase distances/difficulties slowly. Don’t overwhelm them.
*Pick rides that are really pleasant–rails to trail path? Low-traffic rural roads? Those are good. The shoulder of a busy highway–even if it has a wide shoulder–is not fun. You want them to enjoy it! I realize that sometimes unpleasant roads are unavoidable, but do what you can to minimize them.
*Let them set the pace. Our first few tours, Shawn almost always rode behind me (maybe he was just looking at my butt?), and I went however fast I went. If you can ride significantly faster, I realize it will be frustrating to poke along. But few things suck more than feeling like you’ve been left behind. The same ride can be challenging and fun if someone is riding with you, but if you feel alone and left behind, you will hate it and wonder why the $&% you decided to do this.
*If there really is a skill/speed/equipment gap, feel free to carry more of the stuff. It will make them faster and you slower.
*Take frequent breaks to eat a little and stretch and take pictures (this is good advice for everybody). Ask if they need a break here and there, they may be too embarrassed to ask you to stop but relieved if you suggest it.
*Be honest about the route. If there’s a steep-ish hill, say so. If there’s a chunk of highway you have to ride, let them know. But always make it clear that you think they can do it.
*On a similar note, if you mess up, fess up. “I’m sorry, this road had almost no traffic the last time I was on it.” “I’m sorry, that hill was steeper than I remember.”
*Don’t be a pushy jerk. If they don’t ride clipless, or if they prefer upright handlebars, or if they insist on bringing a heavy sleeping pad, don’t lecture them about how they’re doing it wrong. You can give the pros and cons, but unless it’s a safety issue, let it be.
*Lovely Bicycle! had a very good post on the general subject of “How do I get my spouse to ride a bicycle?” The answer, summed up: Don’t be a pushy jerk. Make it fun. Let them make their own decisions.
And now, for a few links!
The Adventure Cycling Association started with the Bikecentennial route in 1976 (now called the Transamerica), and they still do a great job of helping bicycle tourists. They publish their own (very detailed) maps of their many routes. They lead guided tours, both unsupported and supported. They have a magazine that Shawn and I steal from each other every time it arrives. Their website is loaded with information.
Cycle Wild has the motto “reconnecting people with nature via the bicycle.” They’re local to Portland, which is fortunate for us but unfortunate for everyone else. They lead rides to all sorts of places, most of which are a one-day ride from Portland. Cycle Wild doesn’t charge for the rides, and it’s all self-supported. Going on tours, even short ones, with between three and a dozen or so friends? Heck yes!
Ken Kifer‘s page (RIP) isn’t one I’ve explored much but it looks like there’s lots of info.
Sheldon Brown (also RIP) has a short page of articles about touring, but the rest of his website is also fantastic. I seriously think anyone who likes bikes should look at his website. There is just so much information on almost anything you can think of. Plus, he has lots of info on old British 3-speeds, and that just gives me the warm fuzzies.
There’s a few articles about touring on the website for Rivendell Bicycles, but I recently found out the hard way that some people really don’t like Grant Petersen. You should make up your own mind. And if you win the lottery, will you buy me a Betty Foy? (No, seriously. Please?)
The friendly Russ and Laura have been touring the country and living/writing a Path Less Pedaled. They have many reviews of equipment they have tried, and thoughts on life and bicycle touring.
Last but not least! My fabulous boyfriend/touring mentor Shawn wrote a zine, the Bicycle Touring Primer. It’s only two dollars! You can get it here. The link also leads to his blog. I like his blog, but I’m biased.