Cornish Cottage: Una. You could go on a cute foraging date followed by amazing food and a cosy night by the fire.
Malaga Hotel: Connie. She'd be happy sunbathing by the pool all day, and she'd probably know all the good nightclubs.
Backpacking in Asia: Summer. She hikes regularly and speaks a lot of languages. But the fun part is that she'd be naked whenever she could get away with it.
Route 66 Roadtrip: Rachel! She's not great in the heat, but she'd be great company for the ride. Singing along to everything on the radio. Hot sloppy sex in every motel room. Plus she knows her way around a car engine!