Archaeological research along the littoral of Mexico’s Yucatán Peninsula has led to the discovery of hundreds of pre-contact coastal settlements. Following the work of Andrews (1990), these sites had multiple functions ranging for simple fishing villages to international port sites that facilitated long-distance, canoe-based trade. It is the latter category that I focus on in this thesis. The built environment of these port sites and the geomorphological characteristics of their surrounding coastline certainly played a critical role in the services they provided for traders. While individual site-level analyses exist, I take a broader comparative approach in order to highlight the similarities and differences in how these sites were constructed and in turn experienced by the people who inhabited them and who visited them.