In their work with various educators, artists, and learners around the world, the authors have been exploring what it takes to collaborate successfully across multiple technological platforms and cultural borders. In this article, the authors describe three international collaborations in arts learning that they facilitated and participated in via videoconference between February 2009 and February 2010. They share their successes and challenges using Skype to connect students and teaching artists across the country and across continents. (Contains 2 notes.)