This document proposes a new application called Holiday Simplified that will use predictive analytics to provide personalized travel itineraries for families. The problem it addresses is that currently there is no tool that can guarantee a memorable family vacation, and planning one involves a lot of time searching various online sources. Holiday Simplified aims to target families with children who care more about experience over budget and spend a long time planning trips. It will provide differentiated schedules tailored to families in order to reduce planning time and improve enjoyment. The business model involves a loyalty program and subscription fees to generate recurring revenue.