This study examines the structural and policy obstacles hampering free movement of philanthropic capital across the EU’s ‘sea of generosity’. While free movement of capital is a key element in the EU single market as enshrined in the Treaty of Maastricht, this principle previously focused on the for-profit sphere and efficient markets. In 2009, the European Court of Justice (ECJ) confirmed that the free movement principle also covered philanthropic capital, with Member States being prohibited from restricting philanthropic capital movements and payments across borders. This decision should facilitate cross-border fundraising, investment, and tax-effective giving by both corporates and individuals. Yet, significant regulatory drag hinders the use of fiscal incentives, and to date, proposals for EU-wide policy solutions (e.g. a common public benefit definition) have failed. Using the theoretical construct of regulatory space, we highlight the regulatory space characteristics impacting cross-border philanthropic capital movement. This multi-regulatory space analysis finds that contrasting actions by regulators, disparate national policies and the dominance of tax evasion concerns affect the free movement of philanthropic capital across the EU. We argue EU philanthropy could be expanded if there was greater clarity regarding administrative taxation procedures and support for foreign charities and donors seeking to navigate the straits of comparability.