I was not sure what when I first saw the picture so I reached out to some sources, and yep she went to Hawaii alright.
I don't think she took Tripp however, I think he is with Levi and Sunny right now.
So the question to be asked is, what in the hell possesses somebody to take a newborn on a trip to Hawaii?
I mean it's not like Sailor can enjoy the ocean. Or the sun. Or the local culture.
In fact she will have no memory whatsoever that she even went.
All I know is that I wish I had a job like Bristol keeps claiming to have, because I have not been on a vacation for more than fives years now.