We were a group of 4 and made the decision to try the Conch Tour Train. Be aware that for 4 adults you'll be paying a little over $120 for the tour.
The driver is entertaining as your getting bounced around in your seat over the rough roads in Key West. My wife became a little "car sick" from all the bouncing. The first 50 minutes you need to stay on the train as it takes you through the city streets. You get to see all the main attractions, but you're driving past them. There is a 2nd part of the tour after the train stops for several minutes to allow a restroom break. On this 2nd part of the tour, you can get off at stop C to tour the area on your own.
For us, this seemed to be very expensive for what we got. We would have rather rented of of those 4 passenger vehicles at ~$90 for 4 hours, and done a self guided tour.
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