Planned a bachelor party to PR last year:
- El Yunque is pretty cool, nice hike, nice views of a lot of the island. To be honest we ignored closed trail signs and had a lot of fun checking out different spots
- Different rum distillery tours/tastings are an option. We did the Bacardi tour/tastings which was pretty commercialized but still cool. The bar / outdoor area at the facility is also a very nice place to hang for a bit.
- Old San Juan is definitely worth checking out. There’s lots of cool architecture and old bars/shops, etc. There is a bar called La Factoría that’s ranked in the 50 best bars in North America and definitely worth going. We were there late at night but locals told us it’s good any time of day. Traffic was brutal in the afternoons so getting ubers / getting out isn’t always easy. Maybe it was just when we were there but I’d plan accordingly.
- Drink plenty of Medallas. It’s cheap and we thought pretty solid vs. cheap American beer.
- For food, I would go with street food / cheap local options or go higher end. Given budget restrictions we got stuck going to some mid level places that clearly just want to churn through tourists and it was probably the low point of the trip.
- Be smart, some areas are very safe and others are not. If driving at night, be wary of stopping at intersections, we were told locals often go through reds if there’s no traffic because they don’t want to risk idling at lights. Not scaring you, but it isn’t exactly the US.
- Talk to the locals, if you’re nice and genuine, people usually were friendly. Lots of waitresses/waiters liked that we asked about their home/culture and said lots of American tourists aren’t very friendly.
- Bioluminescent beaches are in PR. We didn’t do this but I found it while researching.
-Have also heard great things about doing day trips to Ponce.
I can provide some additional night life recommendations in San Juan but guessing we were chasing a different vibe than you may be after.