Follow-up here is what we did: (DS19 didn't want to take off work to come. Typical for him.)
Okay, so we left later than I wanted and the kids were hungry so we stopped at Cracker Barrel half way.
We arrived at 1:30 at the Red Train (Stop number 2) on San Marco across from the old jail. I bought 5 Red Train Tickets with my military ID (50% off) so it was $43.00. Got on the red train and then got off at St. George Street. These passes are good for three days. I didn't specify to give me the one day or three day tickets, but from what I just calculated I paid 50% off the one day prices and got three day tickets. I think this is pretty good; too bad we couldn't stay three days.
We walked up and down St. George Street just to check it out, noticed where the Columbia restaurant was. There were tons of places to eat but this is the only one we were familiar with and decided to come back later (didn't walk in to make a reservation at this time...didn't know we should/could have).
Then we walked across the street to the Castillo de San Marcos National Monument. Saw the sign saying military were free so I pulled out my military ID. SCORE HERE. The guy gave us an $80 pass that is a military annual pass to ALL National Parks (Grand Canyon, Yellowstone, Everglades, etc.). So DH says we now have to go to the Grand Canyon. LoL. He has been before we met. I think the Everglades are somewhere we can go before this pass expires. We did get to watch the 2:30 cannon shooting. That was pretty interesting and the kids did like this.
We got back on the Red Train then got back off at the Old House. I love house tours and have done many of them in various cities. The guy gave us a deal as well for being military. We paid $18.00 for the give of us to have a guided tour. I don't want to say the tour was bad, but I was a bit disappointed. I thought we were going to get a tour of more than just one building. Total tour with all of the talking couldn't have been more than 30 minutes. I wouldn't do this tour again.
So then we waiting for the Red Train (holiday weekend) but two trains were too full for us, so they called headquarters and one of their "ghost trains" came to get us. We picked up at a few other stops, but when we got to Ripley's, there was a day train that they combined us with that wasn't full. So we made our way back to or starting point about 4:45 and drove back to St. George Street for dinner.
When we go to the Columbia restaurant, the guy in front of me said they had 6 adults, one baby. He was told to come back in an hour. So I said we had 5 and was told to come back in 1.5 hours. They do take your name and make the reservation. We walked around trying to find something to do (and trying to stay out of the boutique Shoppes). We went back at the one hour mark and they immediately sat us. Our waitress was nice but stressed over the busy holiday weekend. After we ordered our food, probably around 35 minutes later she came by saying it should be no more than 10-15 minutes. DH and I were not timing it but we probably got our food about an hour after we placed the order. The food was just "okay" nothing great or special. DH has ate at the original Columbia restaurant (in Ybor City) at office luncheon but said it has been a few years ago so he doesn't recall how he liked the food then. DH and I just added this to another restaurant we won't go back to mainly because the food took forever and it wasn't really anything to speak of and is overpriced. Our bill was $82.53 and some change not including the tip. They didn't have sweet tea so everyone had a coke, except me I had one glass of Sangria ($6.95)which wasn't close to the best Sangria I have ever had either, just pretty plain tasting.
DH finished his food as he always does. He is out running some errands for me, receipt says he got the Checking Salteado for $19.00 (I couldn't remember name of dish).
DS21 got a 1905 salad with turkey for 10.95. I told him only to get the half as he wasn't really hungry. He ate two bites. :-(
DS11 - his dad ordered him the black bean soup ($3.95 cup) to try. He didn't care for it; the other kids tried it and didn't care for it. I tried it and it was very bland.
DD10 and I shared "the Bambino" ($32.00) which is just a sirloin steak, potatoes, and stuffed mushrooms. Since DS11 didn't have any food, I actually gave him the majority of my share. At least he and DD ate everything I gave them off my plate.

I never finish my food by myself anyways.
After dinner we went back to the car (parked in front of the Castillo de San Marcos National Monument) and noticed the weather was quite nice for pictures, so we took a few more pictures before the rain started coming down. J Then we just jumped in the car to make the 2.5 drive back to where we were staying in Georgia.
We didn't even make it over the bridge to the lighthouse. Overall we should have gotten there a few hours earlier if we wanted to add the lighthouse or alligator farm. I don't think we will go back here anytime soon with the kids. I don't think the kids really enjoyed it that much to want to go back.
Our next day trip will be to Savannah, but DH is thinking that we won't take the kids with us there. Not sure if we will make it there before or trip to New Orleans (DD cheer competition). But we have been to New Orleans last year for the cheer competition, and several other trips prior. We enjoy New Orleans. I guess if St. Augustine had a Cafe du Monde, the kids might have enjoyed it more.
One major disappointment is I thought we would see more historical reference to St. Augustine as San Agustin. Just a personal gripe since my husband wanted to go with the traditional spelling for DS11. My FIL is Agustin, DH Augustine (nurses spelled this way and his parents didn't know they could fix it) and DS11 is Agustin. Everyone mispronounces his name! Thought it would have been cool for him to see his name spelled in the traditional form there. I didn't see it once.