Bikeability assessment is essential for advancing sustainable urban transportation and creating cyclist-friendly cities, and it requires incorporating users' perceptions of safety and comfort. Yet existing perception-based bikeability assessment approaches face key limitations in capturing the complexity of road environments and adequately accounting for heterogeneity in subjective user perceptions. This paper proposes a persona-aware Vision-Language Model framework for bikeability assessment with three novel contributions: (i) theory-grounded persona conditioning based on established cyclist typology that generates persona-specific explanations via chain-of-thought reasoning; (ii) multi-granularity supervised fine-tuning that combines scarce expert-annotated reasoning with abundant user ratings for joint prediction and explainable assessment; and (iii) AI-enabled data augmentation that creates controlled paired data to isolate infrastructure variable impacts. To test and validate this framework, we developed a panoramic image-based crowdsourcing system and collected 12,400 persona-conditioned assessments from 427 cyclists. Experiment results show that the proposed framework offers competitive bikeability rating prediction while uniquely enabling explainable factor attribution.