Tracy and I are spending a week in Maui this December. I would really like to take along my bike and ride for a couple of hours each morning. I’ve wanted to do this the last few trips out, but never got it all together. Guy tells me that I just need to go to a bike store, ask for one of their used bike boxes (free), pack up the bike and ship it UPS. This should cost $50 each way.
I searched for “how to ship a bike” to see about getting more insight and found surprisingly little. Hmm, if only there was a site with user contributed content where someone could share their own advice on matters such as shipping a bike 
I did come across ShipBikes.com, an intriguing (and expensive) service.
IMBA used to have a partnership with airlines where they’d ship members bikes for free. Looks like that’s discontinued…
The Bicycle League used to also offer a “bikes fly free” benefit but they also discontinued the service. I never liked the idea since you had to book your flight through a central travel agency.
[...] I’ve written before about how I wanted to take my bike on my Maui trip this December. Well, that didn’t happen. I was convinced (by Guy) that I should ship my bike instead of taking it on the flight. It turns out that you can’t ship via ground to Hawaii (duh) and FedEx and UPS charge around $150 each way. So, I didn’t take my bike at all. Next time, I’ll pack it up and bring it as luggage. [...]