The 28 students making the trip belong to Tamalpais High School's baseball and softball teams.
Other American students have gone to the island country before, but it is believed they are the first high school team in the nation to go to Cuba to play against students there.
"We have several dozen bats," said Tam High softball coach Erin Lawley. "We have also I believe 75 gloves, softball and baseball, helmets, cleats."
Baseball player Kevin Jordan added, "I just hope to learn how they play the game. I'm sure it's different than the way we do."
This is also a goodwill trip. The group plans on taking several bags full of sports equipment to donate to Cuban youth.