It can be overwhelming to realize how much of the world there is to see and how limited one’s time and resources are to experience it all. While there is no shortage of inspiration, from hundreds of pre-madebucket lists (including from Outside’s adventure travel company Outside Go, says that in her more than 25 years of experience planning dream vacations, the key to traveling well is creating a list that focuses on the types of experiences that will fulfill, challenge, and transform you, rather than of pretty destinations. My bucket list will change over time as I do. But to get started, I talked to Cunningham to create a list of five buckets, or experiences I want to have, and filled them in.