A necessary condition is that the number of island-bridge incidences (or bridge-ends) is even (as it is twice the total number of bridges). As $1^2+2^2+\ldots+n^2=\frac{n(n+1)(2n+1)}{6}$, this means that $n\equiv 0\pmod 4$ or $n\equiv 3\pmod 4$.
Also, it is necessary that $n^2\le 1^2+2^2+\ldots+(n-1)^2$ or else we're forced to have some bridge on island $n$ loop back to the same island.
This condition is equivalent to $n^2\le \frac{(n-1)n(2n-1)}6$, i.e., $6n\le (n-1)(2n-1)$, or: $n\ge 5$.
These conditions are also sufficient: Suppose that $n\ge 5$ and $n\equiv 0$ or $\equiv 3\pmod 4$.
Then we can assign $1^2+2^2+\ldots+n^2$ bridge-ends to the islands such that the $i$th island obtains $i^2$ bridge-ends.
Our task is to match bridge-ends in pairs to form bridges.
It is straightforward to first join island $i$ with $i+1$ in order to ensure that we have connectivity as required (this uses one bridge-end for $i=1$ and for $i=n$, and two bridge-ends for all other $i$). Among all pairings among the remaining bridge-ends, pick one that minimizes the number $\ell$ of loops (i.e., bridges running from an island to itself). Assume $\ell>0$.
Let island $a$ have a loop between bridge-ends $u$ and $v$.
As the remaining at most $n^2-2$ bridge-ends on island $a$ cannot use up the at least $1^2+2^2+\ldots+(n-1)^2$ bridge-ends on the other islands, there exists a bridge between an end $x$ on an island $b\ne a$ and an end $y$ on island $c\ne a$ (whereas we do allow $b=c$).
Then we remove bridges $uv$ and $xy$ and replace them with $ux$ and $vy$. Note that this does not destroy connectivity (we can walk from $b$ to $c$ via $a$) and we end up with at most $\ell-1$ loops, contradicting minimality of $\ell$.
We conclude that either $\ell=0$, as desired.