Several people have asked me how I shipped my bicycle to New York for the Gran Fondo NY. I purchased a box from AirCaddy.com — an ingenuous triangle cardboard box that required me only to remove the first wheel and saddle (plus turn down the handlebars). The box might seem pricey at $99, plus about $100 each way to ship from Florida to NY. It is competitive — and perhaps cheaper — than having your bike shop disassemble and ship in a traditional rectangular box. Plus, the advantage is door-to-door service with FedEx — the bike was at my hotel when I arrived. (You could try taking it on the plane, and it might cost less, but the hassle of moving it through a terminal and into a cab didn’t seem worth it.)
I did consider renting a bike through Gran Fondo — it would have cost a little more than $100 for a Trek 1.2 (similar to what I own) or a 1.5. In the end, I decided I wanted to ride my own bike for such a long distance. If you do decide to rent, remember to take your pedals and saddle, which will make the rental feel a little closer to what you usually ride.