Sentence transformers are language models designed to perform semantic search. This study investigates the capacity of sentence transformers, fine-tuned on general question-answering datasets for asymmetric semantic search, to associate descriptions of human-generated routes across Great Britain with queries often used to describe hiking experiences. We find that sentence transformers have some zero-shot capabilities to understand quasi-geospatial concepts, such as route types and difficulty, suggesting their potential utility for routing recommendation systems.