The deployment of tourism to strengthen diaspora ties is well documented, however sociologists have yet to examine the use of tourism to complicate transnational diaspora allegiances. Jewish tourism to the Palestinian Territories offers a compelling case to study this growing trend, as more non-Israeli Jews are foregoing standard trips to Israel and instead visiting sites in Israel/Palestine that challenge dominant Zionist narratives. Using a mixed methods approach that combines pre/post tour surveys with longitudinal in-depth interviews, I investigate how this emerging form of tourism shapes participants' political views, identities, and activism. I find that tourists often experience significant ideological tension when they criticize a base country, while still seeing themselves as part of its national collective. However, rather than compel participants to sever their ties to the base country (Israel), this tension can actually lead to increased engagement on the part of the diaspora member, even when it is in the form of activism directed against the state. Jewish tourism to the Palestinian Territories appears to facilitate this kind of diasporic tension, while also causing participants to "humanize" a previously demonized population, Palestinians. Though such "humanization" does not always lead to overt changes in political views, it influences participants' willingness to embrace counter national narratives. These results suggest that this unique form of "homeland" tourism can engender political criticism within diaspora populations, while simultaneously solidifying transnational ties. It is this contradictory process - solidifying ties to a base country while promoting political criticism of it - that I discuss in my thesis.