Wooden skimboards float but cannot ride on waves well because they do not float well with people on them, for that u would have to buy a fiberglass or a carbon skimboard. Some good sites to check that I use are; www.exileskimboards.com, www.zapskimboards.com, www.victoriaskimboards.com, or www.skimonline.com. But if you aren't that serious about skimming and just want to keep your wooden one, just stick to wet sand and the shallows brah.
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It really depends how good you are and what kind of wood board you have. I mean its possible but very difficult on wood board the wave would need to be real close.
yeah you can but it is very hard to do ! you will have to thrust out to the waves. most people who do this go to beaches with the waves very close to the shore