Set $d_i = x_{i+1} - x_i$ for $i = 1, \ldots, n-1$. Then
$$
\frac{x_n}{x_1} = 1 + \sum_{i=1}^{n-1} \frac{d_i}{x_1} \quad ,
\quad \frac{x_i}{x_{i+1}} = 1 - \frac{d_i}{x_{i+1}}
$$
and therefore
$$
\frac{x_n}{x_1} + \sum_{i=1}^{n-1} \frac{x_i}{x_{i+1}} =
n + \sum_{i=1}^{n-1} d_i \left( \frac{1}{x_1} - \frac{1}{x_{i+1}} \right) \\
\le n + \sum_{i=1}^{n-1} \lvert d_i \lvert \left\lvert \frac{1}{x_1} - \frac{1}{x_{i+1}} \right \rvert < n + (n-1) = 2n-1
$$
because
- $\lvert d_i \lvert < 1$ and
- all numbers $1/x_i$ are in the
interval $(0, 1]$ so that the (absolute value of) any difference
$1/{x_1} - 1/{x_{i+1}}$ is less than one.
The inequality can actually be improved a bit.
For fixed $i$ set $m = \min(x_1, x_{i+1})$ and $M = \max(x_1, x_{i+1})$.
Then $M < m + i$ and therefore
$$
\left\lvert \frac{1}{x_1} - \frac{1}{x_{i+1}} \right \rvert
= \frac 1m - \frac 1M < \frac 1m - \frac{1}{m+i}
= \frac{i}{m(m+i)} \le \frac{i}{i+1}
$$
and the above method gives
$$
\frac{x_n}{x_1} + \sum_{i=1}^{n-1} \frac{x_i}{x_{i+1}}
< n + \sum_{i=1}^{n-1}\frac{i}{i+1}
= (2n-1) - \sum_{i=2}^{n} \frac 1i \, .
$$
Choosing $x_i = i + (i-1) \varepsilon$ shows that this bound is sharp.