Thanks to everyone that filled out the doodle poll! We have a date nailed down for June 7th.
I've found a wonderful company to deliver bikes to us at the LIRR station and pick them up for us at the station afterwards also. The trail is flat and will be roughly 9-12 miles (don't worry, you have a whole day), and we'll be hitting up 3-4 wineries during the day.
I'm currently reaching out to wineries to see which ones can accommodate a large group/give us a private tasting/special offer. The current number of people that we can take is uncertain, but I assume it'll be about 15 people. Once I have a final cost, it'll be first come (pay) first serve for the spots.