I think all involved on our little trip will say that the ride was a new experience. The 5 boros ride is billed as the biggest biking tour in the world - depending on which account we heard, we were sharing the 30,000 - 37,000 - 32,000 or 42,000. I haven't checked on the final count yet, but safe to say it was in excess of 30,000 bikers - which regardless of which city you're in and how well things are organized 30,000+ bicyclers in one place at one time is ALOT of people. And I must say it was really cool to see that many people on bikes in one place at one time all together. It also creates some obvious problems. There were alot of folks on the ride who hadn't ridden in a while or were just not up to speed on road etiquette. Road etiquette (announcing when you pass, slower riders to the left, etc.) becomes all the more important when you are sharing the road with 30,000 other people. So much so that when we were rolling through Harlem and April (a friend who went up with us) had someone pass her on the right and clip her and caused he to fall. she was lucky enough to sorta clip out of her pedals before she fell and to fall into a spot where a car wasn't parked. We ran the guy off the verrazano narrows bridge later in the ride. (kidding)
All in all if was alot of fun. I have always wanted to ride my bike on a multi lane highway and this gave me the opportunity to do it. We also got a great cross section of NYC. We even got to ride over a couple bridges that are normally verbotten to bicycle traffic. I don't like bridges so much, so I whiteknuckled it and stayed to the center, but it was still pretty cool to ride over the Triboro bridge and Verrazano Narrows bridge on your bike.
I think I would do it again. We'd probably not rush up to NYC right away and have to be so harried, but all in all if was alot of fun and a really fresh and different perspective on the city. You can see our photos here:
Here is a map of where we rode, I borrowed it from another rider because I didn't charge my Garmin all up the night before so it croaked before we headed towards Staten Island.