The present invention relates, in some embodiments thereof, to devices, systems and methods for establishing a fluid passageway between vessels. In some embodiments, the invention provides a system for the engagement and establishment of fluid passageway between vessels, the system comprises a first and second vessels configured to be coupled to each other wherein at least one of the first and second vessels comprises a piercing member disposed within the vessel in a retracted position wherein the piercing member confined within/adjacent a port or aperture of the vessel, the piercing member configured to pierce through a cover/seal of the vessel at about the time of or following the engagement between the first and second vessels, thereby establishing a fluid transfer between the vessels.