Have you thought of a cruise? October would be a great time for a Med cruise and New Years great for a Caribbean cruise.
I cruise with teen boys on Royal Caribbean ships for the most part,we hav been on several others but they like RCCL the best- they live on the basketball court,or at the teen centres. The last ship we went on- Freedom of the Seas,has an ice skating rink,rollerblading,putt putt golf,volleyball and basketball courts, Flowrider (surfing) several pools. There are numerous organised activities for teens, and of course you are at a different resort every day or two,with all the beautiful beaches to go to, jetskis and banana boats and pedalos to ride,snorkeling,swim with dolphins, the list of excursions you can take are endless.
Worth a thought .