Step 1Combine the wine and sugar in a large bowl and whisk well to dissolve. Split the vanilla bean in half and scrape the seeds into the wine mixture. Add the bean.
Step 2Leave small strawberries whole; cut large berries into pieces of similar size. Add them to the wine combination and let them macerate in the refrigerator for at least 2 hours, or overnight.
Step 3To serve, ladle the berries and wine into bowls. Top each with a 1/4 cup scoop of ice cream and a cookie.