A cyclic meander is an embedded oriented loop in the plane intersecting a fixed infinite line, or circle, transversely in a linearly ordered set of $2n$ points. By keeping track of the order in which the loop visits these points, the cyclic meander induces a cyclic permutation on these marked points. Correspondingly, given a permutation on $n$ letters, one can ask whether or not a cyclic meander induces the permutation in this manner, and if not, what is the most efficient way of doing so if we allow more points of intersection? This process gives a way of associating to a permutation on $n$ letters a measurement of complexity of the permutation in question. The principal result of this work shows that the maximum of this quantity, the \emph{meander number}, over all cyclic permutations on $n$ letters, is bounded above and below quadratically in $n$. This result resolves a conjecture of Schwartz~\cite{richtpss} in relation to his work on the topological salesman problem. We conclude this work by constructing families of cyclic permutations on $n$ letters whose meander numbers realize a continuum of growth rates between linear and quadratic.