I booked a private tour with Javier Ruiz of Old San Juan through Tours by Locals for my family of 5 adults ages 44-75. We had a wonderful time and Javier really made the history come alive for us. Our tour was for 4 hours.
We arrived in San Juan via cruise ship and meet Javier in front of Walgreens which was easy to find coming off the ship. We were a little early so I called his cell phone with my US phone and had no trouble contacting him and within minutes he was there right on time. We quickly decided that the uphill walk to the fort might be a bit much for our party so we took the free tram up to the fort. We got the last 6 seats on the tram. That was lucky. The tram then waited a long time to depart even though it was full but that was not Javier's fault. The tram was also very bumpy and hurt my mother's back but that also was not Javier's fault. When we arrived at the top of the hill we all were glad we didn't have to walk it but Javier said it would have been faster to walk. He would have taken us walking but we chose the tram and were glad of it. And I'm glad that Javier was flexible enough that we had the choice.
Javier then recommended to buy two senior lifetime passes which gets 1 senior and 3 adults for each ticket into the fort and other US Parks for life which saved us money one the entrance tickets. Javier had his own pass. You don't have to buy him a ticket. As he showed us around he mentioned the church and I said we will want to see that. He asked if we were interested in churches and I said, yes as Christians we will want to visit all the churches we have time for. So we went in the little church (a chapel really). My mother-in-law loved it and we had a few minutes to pray. The fort had steep ramps and steep difficult stairs and Javier gave us options of which way to go and was very patient as the older members of our party carefully navigated the chosen route. The view from up there is wonderful and you can see a lot of the geography of the surrounding area. Javier took time to explain why this location was so important that it needed a fort and why the various powers were always fighting over it. He showed us how the fort changed over time to utilize new technologies (stuff like canon development and such) and meet growing needs.
When we were done at the fort we began walking back down the hill, wandering through Old San Juan. The old city is beautiful. Reminds me a bit of Europe. We mad a number of stops. I probably can't remember them all to list right now. We first stopped at a coffee shop for refreshments and we each bought some Puerto Rico Coffee to take home. Javier said it was the least expensive of the 3 best places to get coffee in the area. Service was great. Coffee was great. And our party needed the rest. We walked past it at first and as he was telling us about it we said we should go back for coffee. So the stopping to spend money and use some of our time with him for a rest was our idea. Other places we went were an old seminary that is now a college, the defensive city wall, and the cathedral, and a number of other places each with its own rich story. Only the fort had an entrance fee. Although a couple of the places were taking donations. We were happy to donate to the college and the churches because we find education and our religion important to us but there wouldn't be a problem if you didn't donate anything. Javier was also leaving donations at some of the stops himself. He showed us the architecture of the city and the influence of the Catholic church on the area. We ran over our allotted 4 hours and I was telling my family that we needed to let him go but he was enjoying himself and kept on talking for a while more. He really made our day special.
Then I asked for a restaurant recommendation for dinner and he said La Princessa and gave us directions and then he asked about our budget cause it might be too expensive but we were fine with it. He wanted to give us another option but then said if after we get there, if we don't like the menu, the prices, or the ambiance, that we should call him for another suggestion. We left him and had a nice walk between the city wall and the ocean/bay and found La Princessa. It was lovely. We sat outside in a beautiful courtyard. The food and service were excellent. There was a great variety of food and we all found something to enjoy.
Javier is a wonderful tour guide for a small group of 1-6 people. He was very flexible to meet our needs and very knowledgeable. He treated us like friends. You can't go wrong booking a tour with him. You won't be disappointed.