November Bucket List: Caribbean Rum, Reggae, and Ridiculous Barrels

Matt Rott

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Updated 384d ago

The Caribbean is an interesting surf zone, when it comes to swell exposure. Tucked under North America and at least somewhat shadowed from NE swells by Florida, this chunk of ocean was popular with pirates because it was popular with trade ships—and that had as much to do with safe harbours as it did with a tropical climate conducive to the production of sugar and tobacco.

But between September and February, the Caribbean actually gets its fair share of swell, both from early season hurricanes and late season nor’easters blowing down from the Atlantic. November sits right in the middle of hurricane season and winter proper, making it a perfect time to post up in the West Indies and enjoy a dose of sapphire blue barrels.

Puerto Rico

Known as the Hawaii of the Atlantic, this American territory is the ideal blend of Latin flavor, political stability, and tropical perfection. Marquee waves like Rincon and Middles have graced the pages of surf magazines for decades (and even once hosted a Search event), and Tres Palmas is a legitimate big wave spot with Hawaiian power, but the island is holding far more than these big-name spots.

Secrets abound, as do user-friendly waves for intermediate surfers and surf-schooling tourists. The wealth of waves has seen Puerto Rico produce a number of A+ surfers over the years, with Otto Flores and Dylan Graves carrying the flag at the moment.

Like many of the Caribbean islands, Puerto Rico was devastated during the 2017 hurricane season, and it will likely be a number of years before it fully recovers. Prospective visitors should keep this in mind when planning trips. It might also be worth looking into doing a combo surf/humanitarian trip to help the area recover.


Like Puerto Rico, Barbados has a lot of waves on offer, many of which are secret enough to be enjoyed solo—if you can manage to search them out. There is also an active kite-surfing scene on the island, with a number of waves on the north side enjoying strong, consistent winds. But the wave that has put the country on the map is Soup Bowls, the slabby right-hand barrel that featured in Sipping Jetstreams, and that Kelly Slater lists as one of his favorite on the planet. A handful of local talent mixes it up with visiting pros every time Soup Bowls breaks, which typically happens during the winter season.


Despite what the movies tell you, Jamaica is more than dreads, blunts, and Bob Marley. There are waves too—just ask Bull Bay local, surf school operator, and Jamaican surf patriarch Billy Mystic Wilmot. While one of the island’s best waves (The Zoo) was destroyed by Hurricane Ivan more than a decade ago, Jamaica still has a decent collection of noteworthy waves, enjoyed by local rippers and East Coast trustafarians living out their Rasta dreams.

Virgin Islands
While they aren’t the most consistent surf destination, both the US and British Virgin Islands are holding waves, and on their day are as good as anywhere in the Caribbean. Most of the breaks are closely guarded secrets, but some of the better-known spots can see a crowd, especially a certain right-hand point that gets dreamy from time to time.

Panama and Costa Rica

Many people forget that Panama and Costa Rica both have east-facing coastlines that pick up swell from the Caribbean. Panama’s Bocas Del Toro has become a trendy backpacker scene, and is also popular with body boarders and heavy water fiends who are after the area’s thumping beach breaks and offshore slabs.

Costa Rica also has some noteworthy Caribbean waves, including a slabby peak that was made infamous in Allen Weisbecker’s book In Search of Captain Zero.

Secret Spots
In a zone with so many nooks and crannies and such a fickle swell window, there are bound to be some secrets. Benny Bourgeois wave is the best known, having graced the covers of both Surfer and Surfing magazines, but there are more out there for those willing to do a bit of exploring.

Cover shot: James Vybiral

Matt Rott

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