I’m not really an expert on surf destinations and even less so on skate parks, although I am aware of many places that do have good surf beaches. From Ireland I think your two best bets would be either Rincon, Puerto Rico, which has the best surfing in the Caribbean and is good for longer rentals like that. You could get a reasonably priced flight into San Juan, which is also a really nice place with some surfing and great beaches, and then hire a car for the drive to Rincon.
Flights, on the other hand, can be pricey if you buy too early. My recommendation would be to book a resort soon and then put a fare-alert on the flights so you’ll get an email when the fare drops. For the Caribbean the cheapest fares are usually only 2 or 3 weeks out, and since that is a slow period you really shouldn’t have any problem (unless you are trying to go on popular Thanksgiving dates). Most likely the resort prices won’t change much as November approaches, so you could probably wait on that as well. There will definitely be empty rooms when you get there, so the resorts usually don’t start pushing up rates when they will be partly empty. Best of luck on this. -Roger
Anyways, me & my wife are planning for our 1st marriage anniversary vacation (24th December is our anniversary). I stay in Mumbai, India & im planning to keep my travel dates from 16th dec 2016 to 30th dec 2016.I had been to New Zealand for my honeymoon & was one hell of an experience with the beaches..adventure & everything. Well, this time around we plan for EUROPE. I know it’ll be freezing down there in December but how about places like Spain.. Portugal ..France ? southernmost part of these areas? ( we would love beach side destinations & i know water will be freezing cold in this month but just lying on the beach would do as well no need to enter the water)
If you’re a bit more on the timid side, you can always use Yelp and TripAdvisor to get good insights on places people have visited. As a disclaimer, some of the ratings may not be accurate on these sites, so make sure you go through and read some of the more recent reviews that people have written. We did this for a few of the places we visited and had no issues.