If this is the first time venturing out into the breaks of Block Island, you have some decisions to make. Are you going to want a short board or long? Maybe you want to cut your teeth with a stand up paddle board (SUP), remaining completely out of the water (unless you take a spill), or stay on your belly with a boogie board? Or you could just say "hang the board, I want to bodysurf."
Unless you are already an experienced surfer, whichever type of surfing you choose, excluding the bodysurfing, you will save on frustration if you seek out a lesson or two. Block Island has different types of breaks than other popular surf locales. Block Island locals know not only the best spots to go, but the best gear for the adventure. Block Island Sport Shop and Diamond Blue Surf Shop can set you up with lessons and gear for a small fee. The instructors are all proficient and professional. SUP lessons and tours are available at Ocean Adventures located in New Harbor behind BIMI.
Once the lessons are done and you're feeling like you want to conquer the waves on your own, you'll want to venture out to some other breaks around the island. If you've taken lessons, talk to your instructor about the best places for you to find breaks that will work with your ability, or else, look for those boards and bodies in the water.
One of the first rules (or guidelines if you wish), when you paddle out to a new (to you) break and there are other surfers, there is an order to catching waves. The person closest to where the wave starts to break has right of way, meaning that it is your responsibility to get out of their way. Other than that be friendly and polite and you'll be amazed how helpful everyone else in the water can be.
As for knowing when to go, there are online surf predictors to clue you in on when the swell is going to come and the possible size. Here's the freebie, Baby Beach, behind the Surf Hotel, breaks best from mid-tide to low and back to mid. When is that? The Block Island Times has tide charts printed inside its pages each week and the website has a link to view online tide charts.
Now on to winter surfing. The gear buy-in is not inexpensive. A good winter wetsuit will run upwards of $300 if not more. 7 mil. gloves and boots will be another $100. The upside is you only lay out that kind of money once every 3 years or so. The reason for putting down that much is that due to the number and intensity of the winter storms that put to sea south of Block Island, the conditions are bigger, cleaner, and last a day or two on average.
Lessons are on a case by case basis in the winter, as the shops are open by appointment only but a few instructors stay year round (keep in mind, locals go on vacation in the winter, also).
If you do brave the Block Island cold, your reward will be clean empty waves. And you might meet a seal or two while you're out there.