The caravan runs through Friday, and will visit Boston-area schools and hospitals.
One Duck Open Sleigh, a Boston Duck Boat filled with the trophies and Red Sox players, will visit three local businesses today for a Red Sox Pop Up Holiday Party, where the winning offices will get to take a holiday photo with the trophies and a visit from Wally the Green Monster.
Pitchers Craig Breslow, Brandon Workman and Drake Britton are expected to attend, as well as catcher Ryan Lavarnway, pitching coach Juan Nieves, assistant hitting coach Victor Rodriguez and bullpen coach Dana LeVangie.
The winning businesses will also receive 20 tickets to a 2014 Red Sox game and World Series merchandise and memorabilia. Businesses can tweet @RedSox using the hashtag #WeWantTheTrophies to tell the Red Sox why their office deserves to be chosen.
The Holiday Trophy Tour leads up to Christmas at Fenway, which is the first chance to purchase Red Sox tickets for the 2014 regular season.