A man who recently lost his wife and unborn son leaves for a road trip with his little brother, who’s determined to help him work through his grief and move on.

I can see the light but not the end of the tunnel – you need a destination. For me and my little brother, this would be some childhood place that we were fond of and always wanted to get back to. From your title I would assume this destination is an e.g., lighthouse, parasailing, you get the idea.

Example:
“A grief-stricken widower sets out with his younger brother on a bereavement road trip to Oregon’s Split Rock Lighthouse.

The more intriguing/haunting destination the better, take care.