By both Luna and Doflamingo's calculations the rendezvous island was a full two days' journey, provided the winds and currents held their course.
As the dawn began to slowly break over the horizon, Luna took her place at the bow, settling down for a nice nap.
"What do you think you're doing?" growled Doflamingo angrily.
"Taking a rest," Luna replied, "since I did all the hard work of breaking us out."
Doflamingo sputtered indignantly, but it was too late. Luna had fallen asleep.
Luna was falling, falling, falling….
"Bright little filly," a wizened voice echoed, "Not as bright or as talented as her sister, of course, but that's to be expected…"
"Well of course we all respect her," a loud, pompous voice cut through, "but what can she really expect? Nopony ever sees her in waking hours…"
"Little sister, don't be silly, of course they'll like you, you're my sister after all…"
"Little sister, what have you become…?"
The temperature dropped at those words, the snow muffling the voices of a time long ago, the wailing of the windigos cutting through the dream.
There was the ache of starvation, the bite of cold, and in the distance, a child screamed.
When Luna woke, it was to a beautiful twilight, the soft pastels reflecting gently off the ocean, turning the water a soft orange and pink color.
"You know," said Doflamingo suddenly, "everytime I begin to think you're too annoying to keep alive, you go and do something interesting." He leaned in, his eerie sunglasses reflecting the light of the full moon. "Who's Celestia?"
Luna felt a chill of cold fear at the name of her sister. "Nopony," she said quickly, "I mean, nobody. She's nothing." Luna's voice took a bitter and dark tone.
"Doesn't sound like it," Doflamingo leaned closer, "What are you hiding, Luna?"
Aside from the fact she was a monster from a distant pony world? "Nothing," she replied, "and I tire of this line of questioning." She got up from her position, moving as far as she could from the feathered man.
She took the empty place at the stern and looked to the stars to get her bearings. Doflamingo kept watching her, the weight of his stare unsettling her more. "One day," he said, "I'm going to figure you out."
Luna sighed in frustration. "Everyone has their secrets Doflamingo," she said, "leave me to mine."
"Not when it's so interesting," Doflamingo parried, "and anyway, I won the bet."
"You did not," Luna squawked, pointing her finger at him accusingly, "the dealer said we both won." She drew a breath of courage for what she was about to do.
"Tell you what," she said, "I'll join your crew, but in return I want you to stop pestering me."
"No promises," Doflamingo smirked, "but I'll leave off for now, my lady." He got up an loomed over her again, his sunglasses gleaming darkly. "But I have to warn you not to betray me. My crew is Family, and Family doesn't betray each other, right?
In Luna's experience, that was exactly what family did, but she kept her mouth shut. "I had no intention of doing so, so I suppose we'll be fine."
She reached out her hand to shake, "Just don't expect me to call you Captain."
Doflamingo smirked, "I wouldn't expect anything less from you."
They shook hands.