W I am thinking that we may just take the trolly around that you can get on & off whenever... I assume this is something we don't book ahead of time but I really don't know?
I have seen the "trolley" mentioned a couple of times..if it is in reference to the Conch Train Trolley Tours, we have done this and I can provide some insight. But to be sure we are all talking about the same thing:
Now I know there may be another trolley tour and this is why I am asking, since maybe the other one operates differently.
However if it is in reference to the Conch Train, I just want to mention how this tour works. We went on it in 2006 and really enjoyed it. But it isn't a multiple stop get off wherever you want thing. It is a pretty structured sightseeing tour, and while it did make one stop where we could have "stayed behind" and caught a later train, this stop was only a few blocks from the end and in an area on Duval Street that we had already been at.
Here is the description from the
website
The tour begins at the Front Street Depot and ends right behind it in Mallory Square. Once you have your ticket, climb on board and take your seat, as you are about to embark on a terrific 90-minute journey through time. During the tour, the train will make one loop through Old Town Key West. There are two stops, once at Station Depot, allowing for a 10 minute rest break where you will find refreshments and shopping. Bring your ice cream and home made fudge back on board to continue your tour. The second stop is at Flagler Station, for just a few minutes. The second stop is also where those who wish to can disembark to see the sights and choose to catch a later train.
Our opinions on the experience are that it is very pricey for what it is ($29/adult, $14/child), but that said we really, really enjoyed it and would do it again (and plan to!). For a 90 minute experience it moved quickly (sometimes too quickly as you fly by some points of interest with the vehicle not stopping) but never got boring(at least not to me). Don't plan on using this tour as an opportunity to stop and get photos at the Southernmost Point- ours drove by, but did not stop (and it is not listed as a stop in the route map) Most of the entire 90 minute experience is spent in the trolley. Our second stop (the one where we could have chosen to stay off and catch a later train) was at a rather large gift shop. We did enjoy buying chocolate covered key lime pie on a stick there (along with everyone else on the tour), but the stop was only about 20 mins long (not very long when all 50+ ppl ont he train are in line @ the cash register buying their pie). On our tour I don't believe anyone selected to stay behind and catch another train, and if you do this there has to be availability on later trains, plus it is only a one-way thing (you can only catch it where you left off and only experience the part of the tour you had not yet, so it isn't a get-off, get back on, get off again kind of thing). The trains depart every 30 minutes.
Lots of info @ the website including route map and pricing- there is a disount available if you purchase online in advance but it is only a couple of dollars. There are also bundle packages that include various museums and points of interest..
see bundles here
They do offer group charters (LOL!) not sure if that costs extra. I'm sure we could set a time and all show up and take that train to have a
DIS CONCH TRAIN TOUR
If anyone has specific questions, fire away. I do have pics somewhere but they are mostly of the "sights" you get to see.
Anyway hope that info helps!!
The treasure hunt sounds like fun and I know my kids would love to be a part of it. I live in a rural area so I am not sure what I could bring for it but I would certainly be willing to help out with whatever I can or send money...
to me
and greet, so here we go.
So we get a BIG re-do!! 
AT the very least, we will DEFINITELY see each other at Nachi, right? 
