I have not been very brave when it comes to taking both my toddler and infant to a nice sit down dinner but I did attempt it a few weeks ago. We had a family dinner with my parents at Olive Garden. It was awesome and here are a few reasons why it went so well.
-We were given a table big enough to expand and it was located in a far corner so we weren't too concerned about disturbing other people.
-Abby, my 5 month old had a car seat sling that she was perfectly happy in while we ate which was great. These slings allow for upright and reclined positions with the car seat so perfect for a sleeper or a player.
-Grandma and Grandpa visited with both children and were available as a back up set of hands if anything went awry. Thankfully nothing did.
-Kid friendly food was available for Dylan, my toddler.
-The waitress was very nice and accomodating. She actually had a child my toddlers age so she knew how to talk to him :-)
The only thing that could be considered questionable was when my mom decided to teach Dylan to squish his cheeks like the guy in the cafeteria in the movie Animal House. Thankfully he wasn't successful and I gave my mom an evil glare to make her stop :-)
Overall we had a great experience going to a sit down restaurant with both kids. Things could have gone bad fast but we did what we could to ensure things went smoothly.