For our purposes, a bracelet of length $k$ (with distinct beads) is an equivalence class of $k$-permutations $[s_1s_2\cdots s_k]$, where two permutations are considered equivalent if they are related by reversal or cyclic shift; for $k\geq 3$, there are $2k$ permutations in each class, so there are $\tfrac{1}{2}(k-1)!$ distinct bracelets of length $k$, and the present situation is $k=5$. A maximizing bracelet is one that maximizes the objective function
$$s_1s_2 + \ldots + s_{k-1}s_k + s_k s_1\text{.}$$
Call this maximized value $a_k$. Then by induction, one can show that, for each $k\geq 3$,
- there is a unique maximizing bracelet,
- $k$ and $k-1$ are adjacent in the maximizing bracelet, and
- $a_k = 2\,_kC_3 + 3 \,_kC_2 - \,_kC_1 + 3$.
In the base case, these claims hold because there's only one bracelet and $a_3 = 1\cdot 2 + 2\cdot 3 + 3\cdot 1 = 11$.
So let's assume the three claims hold at a given $k$. Every bracelet of length $k+1$ is found by inserting the "bead" $(k+1)$ between two adjacent beads $s_is_j$ in some unique bracelet $[s_1s_2\cdots s_k]$. The increase in the objective function is
$$(k+1)(s_i + s_j) - s_is_j = (k+1)^2 -(k+1 - s_i)(k+1 - s_j)\text{.}$$
This increase will be maximized if $\{s_i,s_j\} = \{k,k-1\}$, in which case the increase will be $2\,_kC_2 + 3\,_kC_1 - 1$. Inserting the new bead there on the unique maximizing bracelet of length $k$, we get a bracelet for which the objective function takes the value $a_k + 2\,_kC_2 + 3\,_kC_1 - 1$. Now,
- inserting the new bead anywhere else on the maximizing bracelet produces a smaller objective function value and
- inserting the bead on any other bracelet of length $k$, we started with an objective function value less than $a_k$, so we must end up with an objective function value smaller than $a_k + 2\,_kC_2 + 3\,_kC_1 - 1$.
Consequently, there is a unique maximizing bracelet of length $k+1$, $(k+1)$ and $k$ are adjacent, and $$a_{k+1} = a_k + 2\,_kC_2 + 3\,_kC_1 - 1 = 2\,_kC_3 + 3 \,_kC_2 - \,_kC_1 + 3 + 2\,_kC_2 + 3\,_kC_1 - 1 =2\,_{k+1}C_3 + 3 \,_{k+1}C_2 - \,_{k+1}C_1 + 3\text{.}$$
Finally, the value you want is
$$\left. 2k + a_k\right\rvert_{k=5} = 10 + 48 =\boxed{58}\text{.}$$
See OEIS A110610 and references therein (in particular, the essence of this problem was on the 57th Putnam (1996)).