We've been to PR twice in the early and mid 2000s, each time work related, but the wife and kids came along too. We all really enjoyed it and still think fondly back to it. Each time we stayed at large chain hotels in the Old San Juan area, and being native Floridians, it seemed even less like we were in a "different" country. Each trip was around two weeks, and my family would go see different things and places on days I worked. We really enjoyed walking around in old San Juan and trying different restaurants. One day my son had a discovery scuba course and dive with the Scuba Dog shop. Very nice guy, and afterwards he and I did a dive across the bay from a park to the Caribe Hilton Hotel. And the two main forts there reminded us of our own Castillo de San Marco in St. Augustine. We also went to El Yunque one day in a rental car.
On the next trip a couple years later, we felt like we were back in familiar territory in old San Juan, One thing we did different though was to fly right off the bat from San Juan to Virgin Gorda, BVI for a couple nights at Guavaberry resort near the Baths. I dove on the Rhone too while the family swam. Our kids are young adults now, but these trips, experiences and photos are still talked about.