Thanks everyone for the replies!
cj-traveler- Getting back in time for the tour starting is one of the reasons we decided to do a private tour--this way I won't stress as we are the only ones on the tour. From what I hear it is typically a 6-8 hour tour with the group tours, but I want to be certain. I will definitely post my impressions of the private tour company when we return.
I considered heading straight to Sintra on arrival, a lot of other people do this and stay the first night there. That was really appealing because you can avoid the crowds in the evening and early morning and explore the town and sights then. I read that other travelers who did that really enjoyed it. What decided me not to do this was two things--first we really want to get as much time in Lisbon as possible, second I didn't want to deal with the hassle of checking in and baggage in Sintra, then doing that all over again the next afternoon in Lisbon. Our plane tickets were already purchased so I couldn't add another day and spend two nights in Sintra. I figured with the Rick Steves tour we'd be packing up and moving enough, having the same hotel room in Lisbon is appealing. It's definitely something others should consider depending on their circumstances.
Good to hear about Lisbon Riders--after your posts I read other positive reviews of them. Hope Top Ten will impress as well. I'm super excited to see Sintra and glad I read others itineraries and experiences which caused me to choose to go there!
Happy traveling everyone!