Recent EU legislative and policy initiatives aim to offer flexible, innovation-friendly, and future-proof regulatory frameworks. Key examples are the EU Coordinated Plan on AI and the recently published EU AI Regulation Proposal which refer to the importance of experimenting with regulatory sandboxes so as to balance innovation in AI against its potential risks. Originally developed in the Fintech sector, regulatory sandboxes create a test bed for a selected number of innovative projects, by waiving otherwise applicable rules, guiding compliance, or customizing enforcement. Despite the burgeoning literature on regulatory sandboxes and the regulation of AI, the legal, methodological, and ethical challenges of these anticipatory or, at times, adaptive regulatory frameworks have remained understudied. This exploratory article delves into the some of the benefits and intricacies of allowing for experimental instruments in the context of the regulation of AI. This article’s contribution is twofold: first, it contextualizes the adoption of regulatory sandboxes in the broader discussion on experimental approaches to regulation; second, it offers a reflection on the steps ahead for the design and implementation of AI regulatory sandboxes.