So my ****ty job doesn't allow me to go on trips during the summer, and I've already missed out on a trip earlier this year. By late fall early winter I am looking into finally going on a trip to the Caribbean for a week. What is the best island for surf and night life. Trying only to spend about 1500 total.
Dominican Republic is off the hook for nightlife. You may not be functional to surf if you stay up with the chicas every night (drained of fluids, so to speak). The north coast of the DR, in the Cabarete region, can get good waves but can be crowded, flat & tends to blow out every day mid-to-late morning. Barbados is good waves but way touristy nightlife & expensive as all get out. Other people probably have good suggestions on PR & elsewhere.
NW PR or rent a little house in Bathsheba, Barbados. I'm more of a cook at home, bed early, surf all day, repeat the process kinda person though. Not too much into night life especially since participating in that can double the cost of your trip.
Rincon in PR is where you want to go you can find cheap places to stay and food at the road side stands is always good and cheap and its like a dollar a beer
Northwest PR for sure. Not the craziest nightlife out there but the best surf. If you want some good nightlife too, take a night or two at the beginning or end of your trip, stay in San Juan and go out near Condado. You can surf near San Juan if there's some swell around, you're just a lot more limited on wave selection compared to Rincon, Aguadilla, etc., but still something to keep yourself busy during the day if you want a few crazy nights.
The choice is simple, Rincon PR, many have said it, it's just so much easier and less expensive than most other options and the waves are awesome.