While it may not be recognized world class surf, Trinidad and Tobago is super consistent all winter (not to mention the rest of the year). Uncrowded trade swell will keep you in the water while you wait for your long period NorEaster lines to roll in.
Philly to Trinidad is almost always $550 to $600 Round Trip. This trip gets you there for 50% less than that average.
When the opportunity to surf off the beaten path presents it's self I am always tempted to drop everything and go explore. Trinidad most certainly meets the criteria with a relatively untouched northern coast (which happens to be where most of the best surf happens).
Every video I could find on this place looks just straight fun. Nothing crazy, just fun.
Trinidad is the very southern most of the Leeward Islands (a short 7 miles from Venezuela) and therefore is open to quite a bit of swell from three primary sources (depending on the season).
Since these trips are generally toward the end of the year / early next year, you are mostly going to be looking at the Dry Season with stiff trades pushing 5-7ft short periods inter-spliced with the previously mentioned super long period 15 second NorEaster swell from all the way back home Philly way.
That said, it DOES get good.
Unlike the rest of Philadelphia, hopefully this December will find you looking a little more like this:
Free Supporter Trips
As mentioned this stuff goes off toward the end of this year and aligns with the best chances to score some northwest-long-period-goodness. Here's a couple options for those of you who aren't Supporters yet.
*Hint, subscribe and get way more deals.
Per the above image most of these trips are on United, which on one hand is a legit airline (minus dragging that one guy off the plane), on the other their surfboard fees are borderline facist (though substantially better than Delta's $150 PER BOARD).
United is going to run you $150 per bag. So it may be worth renting when you get down there, or stacking all the crew's boards in one coffin.