Best Friend

Pros: Guarantee of zany antics, copious amounts of colorful cocktails, a thousand new inside jokes, and talking about life late into the night. BFF vacations are special because really, is there anyone else you have more fun with?

Cons: Traveling with a best friend can be a lot like living with a best friend: it's a test of intimacy that can make or break your friendship. Did you know your bestie likes to stick to a detailed itinerary and refuses to wash her toothpaste spit down the sink? Are you OK with that?

Take the trip if... having fun is your top priority and you talk beforehand about your preferred traveling styles.