Let $\{D_n\}_{n=1}^\infty$ be a family of pairwise disjoint closed disks in $\mathbb{R}^2$. Is the complement $$ \mathbb{R}^2 -\bigcup_{n=1}^\infty D_n $$ always path connected?
Here “disk” means a round, geometric disk. (As shown below, the answer is no if we allow arbitrary topological disks.)
Note that the union $\bigcup_{n=1}^\infty D_n$ can be dense in the plane. For example, it's possible to find a collection of disjoint closed disks of positive radius whose union contains $\mathbb{Q}\times\mathbb{Q}$.
It is easy to show that the complement of a countable set of points in the plane is always path connected. In particular, if $S \subset\mathbb{R}^2$ is countable, then there is always path between any two points in $\mathbb{R}^2-S$ consisting of two line segments.
It is not true that the complement of a countable set of disjoint line segments is path connected, as shown in the following figure.

By thickening the line segments slightly, one can find a countable collection of disjoint topological disks whose complement is not path connected.
Contrary to the request of the OP, this is still a sketch. I put it here because it points to some relevant literature, hoping that somebody more expert than me will help to clarify it. The question reminded me of this paper by Fischer and Zastrow: the relevant part is the end of p. 12. See also this answer by George Lowther.
You can assume that $\cup D_n$ is dense. Now choose some nice diffeomorphism $\phi:\mathbb{R}^2\to B_1(0)$. Once you apply it, the images of the disks are no longer disks, but $X:=\overline{B_1(0)}\setminus\bigcup_n \phi(\text{int }D_n)$ is still a planar 1-dimensional Peano continuum without local cutpoints (I'm not sure about the meaning of 1-dimensional..), so it is homeomorphic to the Sierpinski carpet by a theorem of Whyburn (Whyburn, Topological characterization of the Sierpinski curve, Fund. Math. 45 (1958) 320–324).
Our space is homeomorphic to $X\setminus \left(\partial B_1(0)\cup\bigcup_n\phi(\partial D_n)\right)$, but these sets we are removing are characterized as being the only non-separating simple closed curves. So under the homeomorphism with the Sierpinski carpet they map exactly to the boundaries of the holes (plus its exterior boundary) and we are left to show that:
But this is easy. Call $S'$ this new awful noncompact carpet. Put $C_1:=[\frac{1}{3},\frac{2}{3}]$, $C_2:=[\frac{1}{9},\frac{2}{9}]\cup [\frac{4}{9},\frac{5}{9}]\cup [\frac{7}{9},\frac{8}{9}]$, and so on. We have $S'=(0,1)^2\setminus\bigcup_{i=1}^\infty C_i\times C_i$.
Put also $G:=(0,1)\setminus\bigcup_{i=1}^\infty C_i$ and observe that $T:=(0,1)\times G\cup G\times (0,1)$ is path connected and $T\subset S'$.
Now fix any $p_0\in T$. Given any $x\in S'$, we wish to connect it to $p_0$ with a path in $S'$. Let $x\in Q_1$ where $Q_1$ is one of the $9$ closed cubes with side $\frac{1}{3}$ (those in which $[0,1]^2$ is divided when constructing the Sierpinski carpet). Choose some $p_1\in T\cap \text{int }Q_1$ and connect $p$ to $p_1$ with a path of length $<3$ (namely a path formed by at most three line segments).
Replace $[0,1]^2$ with $Q_1$ and iterate this step using self-similarity. Iterating infinitely many times we get a sequence $p_n\to x$ and paths in $S'$ connecting $p_n$ to $p_{n+1}$ with length $<\frac{3}{3^n}$, so that concatenating them we get a path from $p_0$ to $x$. $\blacksquare$