It's not too late to be a modern day pioneer. Surfing is not yet a very popular activity in Cuba, so there are plenty of waves to ride on beautiful beaches, without having to wait your turn. Keep in mind that you may not easily be able to find surfing equipment to rent.
It's little surprise that some of Cuba's beaches make for excellent surfing, what is a surprise is that the sport has yet to catch on — after all, surfing isn't exactly new. Slowly but surely, that's changing. For experienced surfers bound for Cuba, Guardalava and Baracoa have beaches that offer large swells. Serious surfers may even travel there at the tail end of hurricane season (August-October) for the big waves.
In general, the best time to visit Cuba is during the dry season (November to April), but in addition to larger swells during the wet season, the waters of the Caribbean tend to get warmer. Surf is fairly unreliable along Havana's coast, but determined surfers still regularly visit the local beaches. Calle 70 or Playa Guanabo are just outside the city, and are popular with visitors and local surfers alike.
Playa Mar Verde and Playa Buey Cabón, outside of Santiago de Cuba, may be better for more experienced surfers due to their point breaks, or waves that break over rocks under the water.
For new surfers, Varadero is a great place to try to catch waves. Private and group surfing lessons are available here.
Unfortunately, the reason it may be difficult to rent equipment is the same reason it will be a challenge getting to Cuba and obtaining entry to Cuba — lingering challenges from the communist government. Although you can get to Cuba by air and sea (land isn't an option for this island nation), that's moot if you are legally prohibited from entering the country. However, once you're granted entry, the beauty of the outdoors and amazing culture await you.
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