I have the following
Conjecture. A metric space $(X,d)$ can be isometrically embedded in the plane $\mathbb R^2$ endowed with the standard metric $\rho$ iff each four-point subspace of $(X,d)$ can be isometrically embedded in the plane.
To build such an embedding $i$ we fix three different points $x$, $y$ and $z$ of $X$ for which the triangle inequality is strict and fix an arbitrary embedding $i_0:(\{x,y,z\},d|\{x,y,z\})\to (\mathbb R^2, \rho )$ (case when there are no such triple $\{x,y,z\}$ have to be considered separately). Let $t\in X$ be an arbitrary point. It seems that there exists an unique point $t’\in \mathbb R^2$ such that $d(x,t)=\rho(i_0(x),t’)$, $d(y,t)=\rho(i_0(y),t’)$, and $d(z,t)=\rho(i_0(z),t’)$. Put $i(t)=t’$. Then it seems that $i$ is an isometric embedding.