Chose Old Town Trolley after reading reviews for all tour companies on Trip Advisor. Did not purchase tickets in advance to be sure of the weather. Parked in a garage nearby and walked to the #1 stop (Marriott Long Wharf/Aquarium/Faneuil Hall). Quick and easy ticket purchase around 9:00 a.m. on a fair weather Saturday and we were on our way in under 5 minutes. Trolley had about 10 riders when we boarded and Buck was our driver. Can't say enough about Buck...he was absolutely great! Very knowledgeable, humorous, courteous and it was great fun to ride on his trolley. We enjoyed learning all about the historic sights as we made our way around Boston.
At each stop more passengers boarded and by the #5 or #6 stop the trolley was full and passengers wanting to board had to wait for another trolley. Buck always checked if there were empty seats at each stop and was courteous to those having to wait for another trolley. He stated about 10 minutes for another one. This is the only reason for the 4 star rather then 5 star rating. The trolley was full at many stops with most people staying on board therefore no spots for those waiting. Many of those sitting around us were going for the full loop tour to see everything first then hop on/off the second go round.
Stop #12 (Fenway Park) was our first goal for the day. After the tour we returned to the location where we were dropped off (#12) and there was a trolley sign (noted some others mentioned there weren't signs....there was at stop #12 but can't say for other stops). We were the only 2 people waiting and within a few minutes a trolley arrived and Lil Bean (driver/guide) said there were 2 seats on the very back row which is a bench seat. This seat can hold various numbers of people depending on size (more if children). We were able fit in the middle and off we went. Only problem with this seating is you cannot see as much and can't really get any photos. Next two stops had people waiting and there was no room. Eventually a few passengers got off the trolley and we moved to an empty row in order to see better and take photos.
After leaving the trolley at Stop #1 where we started the day we did the free Harbor Cruise that is part of your trolley ticket. Thouroughly enjoyed the cruise! You get beautiful views of the city and get to see the USS Constitution. Be sure to take advantage of this freebie if it's part of the ticket when you visit.
We only had 1 day to visit Boston so Old Town Trolley was perfect for this visit giving us an overview of the historic sights around town and a drop off at Fenway Park....and all without having to navigate and drive your own vehicle. Definitely would have used the free second day if possible to visit a few other places along the route if time had allowed.
While waiting for a trolley with room might be a possible drawback to those with limited time, I still recommend Old Town Trolley tours if you want a fun way to see the city with great guides who can entertain and educate while navigating city traffic and narrow streets. We enjoyed our experience and it sure beat trying to drive around town to see all these locations.