Hard Rules, Soft Preferences: Bridging Reasoning, Learning, and Optimization for Personalized Packing Checklist Generation

Travel planning is a demanding stress test for tool-using LLM agents: a usable itinerary is a single artifact that must be right along many axes at once - every flight, hotel, and attraction must exist and be bookable, the days must be physically traversable, the total must clear a budget, and the plan must serve a traveler whose needs are only partly stated. Existing agent benchmarks reward these properties one at a time and grade the final output with soft or LLM-judged rubrics, which cannot certify that a returned plan is executable and are neither reproducible nor auditable. We introduce TREK (Travel Reasoning and Evaluation Kit), a benchmark for feasible itinerary synthesis: producing a single plan that is jointly constraint-correct, hallucination-free, spatio-temporally executable, budget-valid, and responsive to the traveler's unstated persona needs. TREK comprises 800 multi-constraint tasks - 533 feasible and 267 provably infeasible with typed route/entity/budget causes - over a synthetic, internally consistent knowledge base of 212,530 records across 375 cities and 13 personas, served through a production-style tool sandbox of validated RESTful APIs. Every task is scored by a fully deterministic, rule-based evaluator with no LLM judge and ships a human-verified gold reference that scores a perfect 1.0 under that same evaluator, so the ceiling is demonstrably achievable and every remaining gap is an agent limitation rather than scorer strictness. Evaluating 15 LLM agents across nine constraint dimensions, we find that even the strongest (GPT-5.6) produces a fully-feasible plan on only 46.2% of solvable tasks, with a median of 6.6% and a floor of 0.0%; satisfying travelers' unstated needs emerges as the universal bottleneck, unsolved even at the frontier. We release the dataset, tool sandbox, deterministic evaluator, and agent code as a fully reproducible benchmark.

Generating personalized trip itineraries is a complex planning task and involves a tension between hard combinatorial feasibility and soft latent desirability. Classical optimization enforces constraints but fails to capture subjective traveler preferences. While learning-based approaches model preferences, they cannot guarantee feasibility. Mobile deployment imposes additional resource constraints on both. To address this, we propose Plan, Learn, Adapt (PLA), a three-stage framework for personalized on-device itinerary generation. The Plan stage builds a heterogeneous ensemble of lightweight planners that produces structurally diverse feasible candidates. From pairwise itinerary comparisons, Learn fits a compact Bradley-Terry reward model that captures emergent schedule properties such as pacing, geographic coherence, and day balance, which per-POI signals miss. Finally, Adapt applies feasibility-preserving local refinement within a device-aware compute budget; every intermediate state is feasible by construction. On 2,519 pairwise human comparisons across more than 100 U.S. cities, the reward-guided ensemble achieves a 67.8% win rate, 11.2 percentage points above the best single planner, with 100% feasibility. Three frontier LLMs, GPT-5, Claude Opus 4.5, and Gemini 3 Pro, achieve 0% feasibility under the same constraints. The reward model generalizes across held-out cities, with a 67.6% mean leave-one-city-out accuracy. In production deployment within FlyEnJoy, PLA increased itinerary completion rates by 91%, with 109.9 ms average on-device latency.

In our deployed travel-planning service, most users give minimal inputs or free-form requests rather than the structured constraint checklists assumed by existing benchmarks. We therefore present TripScore, a behavior-grounded benchmark and evaluation framework built from real user logs and calibrated against 1,468 pairwise judgments by 203 travel experts. TripScore couples a hierarchical feasibility gate (format and commonsense) with a unified, point-wise reward that aggregates soft quality and preference fulfillment. Using TripScore as both evaluator and reward signal, we benchmark direct prompting, test-time compute, neuro-symbolic solvers, code agents, and fine-tuning. We find that reinforcement learning fine-tuning (e.g., GRPO) provides consistent gains over other approaches under the same base model and practical latency.