Yankee, thanks a ton! That is excellent info for me. So out of the three which would you choose: DR, PR, or Barbados?
For surfing I'd pick Barbados. Because it's an island, some break somewhere has swell. Because it's a small island, you'll not drive more than 40 mins to a break. You get better, more consistent waves there than the DR. The water is tropical warm. Food is fresh. Bajans speak English & are respectful / polite. You won't see road rage, heck, you probably won't even hear a car horn while there. Downside to Barbados is that it can be expensive, primarily eating. We rent a condo. Then,shop for food to keep costs down; but food is expensive there. You can save food money eating at local spots such as the Oistin's fish market. Cheap & damn good seafood.
DR is cheaper than Barbados (but not even close to el cheapo what it was 8-10 yrs ago, they've adjusted ther prices higher to gringo prices), great nightlife, single man's paradise (chicas!) & a party culture. Winds, however, limit surf time & if there's no swell, you're running up your bar bill because it's a huge island (largest in the Caribbean behind Cuba) & you can't just drive to another break in a few minutes.
The only knowledge of PR is what I research on this board & others - - haven't been.
i would suggest Central America. Nov/Dec is the beginning of the Off season so the waves wont get too big, you'll be surfing waist-head high waves everyday. and the conditions will be offshore most likely all day. For your first trip to Central America i would suggest Costa Rica, there tons of tours and plently of things to do other than surf for your girl too. Nica you'll score better and less crowded waves, but the restaurant/bar/party scene isnt as hopping. unless you go to San Juan Del Sur.
PR is a good choice but the lineups are almost always packed (esp if your going to the main surf areas). DR is a good choice too but it can get windy, same with Barbados. plus were talking about lake atlantic, it can go completely flat even during the on season.