Two Brothers Sailing Chicago offers tours, packages and sailing lessons that can be customized to accommodate the plan for the day. The Vagabond is an Ocianis 393 Benetou and the primary sailboat of choice for charters and lessons. Also in the fleet is a variety of boats called up when we have parties larger than 10 persons. The Captains are USCG licensed and the ship has been inspected and certified by the Coast Guard, with annual inspections to insure your safety and comfort.