This three-day, Caribbean-themed wine event provides separate tastings at 11 different Niagara Wine Trail wineries for a single $20 pre-sale price, or $25 at the door, with each winery representing a different island theme. You'll get a commemorative wine glass that you take from place to place, and participants will get a chance to win a $2,000 gift certificate for a Caribbean cruise. Participants need to schedule their own transportation from site to site, which is offered by local companies.