Multi-Dimensional Evaluation of Sustainable City Trips with LLM-as-a-Judge and Human-in-the-Loop

Evaluating nuanced conversational travel recommendations is challenging when human annotations are costly and standard metrics ignore stakeholder-centric goals. We study LLMs-as-Judges for sustainable city-trip lists across four dimensions -- relevance, diversity, sustainability, and popularity balance, and propose a three-phase calibration framework: (1) baseline judging with multiple LLMs, (2) expert evaluation to identify systematic misalignment, and (3) dimension-specific calibration via rules and few-shot examples. Across two recommendation settings, we observe model-specific biases and high dimension-level variance, even when judges agree on overall rankings. Calibration clarifies reasoning per dimension but exposes divergent interpretations of sustainability, highlighting the need for transparent, bias-aware LLM evaluation. Prompts and code are released for reproducibility: https://github.com/ashmibanerjee/trs-llm-calibration.