since i've done this ride about 10x this summer, my suggestions/advice:
-its about 55 flat miles, you should be in shape to ride about 3 1/2 hours, even with the experience and conditioning, i get a little sore and tired at around mountain view which is still about 15 miles away from SJ
-flat flat flat no hills no hills no hills, easily done fixed gear brakeless whether you rock a 50x15 or 48x17 or 46x19 whatever, any gearing can do this
-bring SUNSCREEN, even tho most of us here are yellow asians or brown mixers, the daytime sun for 3 1/2 to 5 hours can be brutal and burning not to mention skin cancerous!
-bring SPARE TUBES cuz flats are a possibility especially along some of the surface street areas prone to debris like glass and thorns, also bring some Clif bars and energy bars, you'll need it, hungry folks!
-wear shorts or some kind of bike clothing cuz your jeans and all-over print hipster gear will feel pretty gross after riding 3 1/2+ hours and 55 miles
-if you need to bail out at any point during the ride there is always a Caltrain station nearby, we will be riding pretty parallel to the Caltrain corridor, so bring extra MONEY too!
-i suggest to leave SF no later than noontime NOT TOO MUCH LATER cuz with a larger group and different skill and speed levels, this ride could take up to 5 hours and since the sun is setting sooner these days, its not as safe to be riding in the evenings, so if we leave SF by 12 noon, we will arrive in SJ at 5pm at the latest, or even 330 or 4pm at the earliest!
-thats about it, come do this ride, it is fun, challenging, and scenic, and the more we have the more riders we have, the merrier!
-i suggest that we all have dinner and drinks AT THE END OF THE RIDE, if we eat alot during the ride, people will get lazy and not finish the ride, so eating at the end will be like the reward for doing the whole thing!
-i am better for SATURDAYS so SATURDAY is my vote!
-Bennett