Travel agent, Hester Monday, has been keeping a secret … Thanks to her fear of flying, she hasn’t been on a plane in years. Now Hester wants to make a good impression on her newest client, Jake Oakenfield, who was heroically injured saving an old lady, and is now laid up in a luxury hotel. For Jake, unable to return to New York, binge watching Netflix just won’t do. He wants Hester to invent the ultimate escape and re-create her most magical holidays abroad from the confines of his hotel room. As their perfect mini-breaks around the globe take on a life of their own, Hester wonders if her world of make-believe is all starting to feel just a little too real…