How many times per year do you ship wine to club members? June 02, 2020 18:06 Updated We release wine to our club members three times per year, normally in October, February and May. Related articles How do I arrange for my complimentary wine club tasting? Does my wine club membership expire? How do I make a change to my wine club membership? What is your inclement weather policy in case of rain or cold weather? How do I join your wine club?