If I were to take my friends around the island I would start with Old San Juan. There is so much to do there. What would I do and where would I go.
First I would start with a day in Old San Juan. The city has so much to offer, but some of the things I would point out is the amount of churches in the Old City, the fact that it is surrounded by walls and has a rich heritage. So I would drive in through San Cristobal Castle, see the City walls in the north which is next to La Perla, and low income community that has the best sea side location in the city other than El Morro. If you compare El Morro to the fortification in St Augustine, it is at least 18 times larger and has 3 different levels. There is also an underground tunnel between both fortifications which is now damaged and closed to the public. We have garitas or sentinel posts that have a little ball on the top which are typical of PR. In fact a stamp issued by the US postal service has a painting of a garita. Guards would stand watch all night and there is one particular garita, located at the bottom of a cliff which has its own mysterious yet romantic legend, too. The city is full of quaint shops, good jewelry stores, and items from other countries, particularly Spain which still has close ties to Puerto Rico; so you might want to come ready to buy some souvenir. We could visit El Morro or San Cristobal, so make your pick.
On our way to La Capilla del Cristo, you might want to get an ice cream at Ben and Jerry's and I would point out, La Capilla de San Jose and the San Juan Cathedral, which we could step into and perhaps say a prayer for a safe trip around the island. Then down to La Puerta de San Juan, a beautiful shaded street and and buy a limber, a homemade ice fruit flavored treat to cool off with. Next we would arrive at La Capilla del Cristo and tell you the story about the two horse racers.
Around the corner we would find the sculpture called Las Mil Virgenes. This last story is a true story of God's goodness and sovereignty in protecting the Old City from a British invasion. Then down to shops and move our car to La Princesa parking and then walk to EL Paseo de la Princesa. La Princesa used to be jail during Spain's "colonial," times but the long walk hosts artisans on the weekends.
As we drive out of the city we would see the Capital building and
El Parque Munoz Rivera where I would point out that this latter one was my favorite memories of San Juan because of its huge sidewalks and gardens overlooking San Juan's rocky shore.
In Old San Juan there are three places to eat that I would recommend: Barrachina with sandwiches and sodas and /or La Bombonera or La Mallorquina, two well known bakery-coffee and sandwich shops. Both have fresh cafe con leche or Posillos.