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.
If the thought of another year crawling to a close has left you feeling a little low, November is the perfect time to give yourself a travel-fuelled lift, with an array of destinations primed for exploration during the penultimate month of the year. Trek in perfect conditions in Ethiopia and Nepal, visit Orlando’s theme parks at discount rates, sample an unusual Thanksgiving dinner in Puerto Rico or don your skeleton outfit for Día de Muertos in Mexico – trust us, the year is far from over!
Southeast Asia is easier to deal with, and there are cheap flights connecting in the Middle East and landing in Bangkok, Kuala Lumpur, and Singapore. Each of those is a very interesting city, and there are many smaller places to go in the same region. In Malaysia there is Penang and Melaka. In Thailand there is Chiang Mai and quite a few others in that area. In Laos you can visit Luang Prabang, which sounds like it could be a winner for you. And there is also Siem Reap, which is home to the amazing Angkor Wat temple complex.