We propose to use tensor diagrams and the Fomin-Pylyavskyy conjectures to explore the connection between symbol alphabets of $n$-particle amplitudes in planar $\mathcal{N}=4$ Yang-Mills theory and certain polytopes associated to the Grassmannian G(4, $n$). We show how to assign a web (a planar tensor diagram) to each facet of these polytopes. Webs with no inner loops are associated to cluster variables (rational symbol letters). For webs with a single inner loop we propose and explicitly evaluate an associated web series that contains information about algebraic symbol letters. In this manner we reproduce the results of previous analyses of $n \le 8$, and find that the polytope $\mathcal{C}^\dagger(4,9)$ encodes all rational letters, and all square roots of the algebraic letters, of known nine-particle amplitudes.