A tanglegram consists of two rooted binary trees and a perfect matching between their leaves, and a planar tanglegram is one that admits a layout with no crossings. We show that the problem of generating planar tanglegrams uniformly at random reduces to the corresponding problem for irreducible planar tanglegram layouts, which are known to be in bijection with pairs of disjoint triangulations of a convex polygon. We extend the flip operation on a single triangulation to a flip operation on pairs of disjoint triangulations. Interestingly, the resulting flip graph is both connected and regular, and hence a random walk on this graph converges to the uniform distribution. We also show that the restriction of the flip graph to the pairs with a fixed triangulation in either coordinate is connected, and give diameter bounds that are near optimal. Our results furthermore yield new insight into the flip graph of triangulations of a convex $n$-gon with a geometric interpretation on the associahedron.