To get a similar experience in the exact opposite way: travel in a big group. In a group of 30 there's usually someone who wants to join, and even if not, you don't have to feel bad about breaking off and doing your own thing for a bit, because no one expects you to do everything together.
You still have the basic structure of the trip to get everyone together for a travel day and discuss your adventures during a long bus ride, so I think it's really the best of both worlds.
I liked the sailing portions in Wind Waker, they're pretty chill. My bigger problem with that game was the number of mcguffins you have to collect. Even if the ship was going lightspeed, most of the game is looking at your map where the next key/treasure/artifact is marked, sailing there, fighting one enemy, repeat. Even after all of the map was explored, it kept going. Member that tiny island you found first thing? Turns out there's not one, not two, but three magic artifacts buried in the sand! Now go fetch, boy.
The only thing that kept me sane was the sound of rolling waves and gently swelling music