One Hill of an Adventure
Personal planning help for the trip you keep putting off.
The resources & guides on this site are free, and they cover a lot. But sometimes you want to talk through your specific situation with someone who has actually done it — whether it’s figuring out which cards make sense for your spending habits, building itineraries for places we know well, or helping you see that the trip you thought was out of reach is closer than you think.
That’s what we offer here. Real help, from real experience, applied to your trip.
60–90 minute call
A focused call where we work through your trip together. Best for people who have a destination in mind but aren't sure how to pull the pieces together, or who want a sanity check on a plan they've already started building.
What’s included
60–90 minute call
We look at your current cards, your typical spending, and where you want to go — and help you build a practical strategy for earning and using points. We've used points to go international, fly business class, and cut the cost of trips significantly. This session shows you how to do the same.
What’s included
Delivered within 5–7 days
You tell us where you're going, how long you have, your travel style, and your budget. We build a complete, custom day-by-day itinerary — including where to stay, what to do, where to eat, how to get around, and what we'd skip. This is the version of the trip we'd plan for ourselves.
What’s included
Discuss after a first session
For people who travel regularly and want a thinking partner they can come back to. We'll help you evaluate deals as they come up, build a points strategy across multiple upcoming trips, and plan as your travel calendar evolves. Best discussed after a first session once we know your situation.
What’s included
Not sure which option is right for you? Just tell us where you are and what you’re trying to figure out in the form below — we’ll point you in the right direction.
Tell us about your trip, your timeline, and what you need help with. It only takes a few minutes.
We'll confirm the right service, answer any questions, and send a booking link to get it on the calendar.
For calls, we meet on Zoom. For itinerary builds, we deliver a document you can actually use.
Yes! Actually, that's one of the best times to work with us. The first international trip involves the most unknowns, and having someone walk you through the logistics, costs, and what to expect makes the whole thing a lot less overwhelming. We've helped people plan first trips before and it's some of the most satisfying work we do.
Absolutely. The session is designed to help you build the right strategy from where you are now. We walk through which cards to get, in what order, and how to structure your spending to earn points as efficiently as possible. You don't need to already have a stockpile for it to be valuable.
That's a fine place to start. One of the things we do well is help people figure out where to go given their budget, time of year, and interests. If you're open, we can also help you think about which destinations give you the most value for your money right now.
The earlier the better, especially if you have a trip coming up. We try to respond to all inquiries within 2 business days and can usually get something on the calendar within a week or two. If you have a firm travel date, mention it in the form and we'll prioritize accordingly.
For single sessions, we include follow-up notes after every call, and you're welcome to reply with clarifying questions via email. For more ongoing access, the monthly advising option is designed for exactly that.
Both. Our own experience is as a couple, but the planning principles are the same regardless of whether you're traveling alone, with a partner, with a family, or with a group. If you're traveling with a larger group, just mention it in the form — some logistics change with group size.
Fill out the form below and we’ll get back to you within 48 hours. There’s no commitment involved — if you’re not sure what you need, just tell us where you are and we’ll figure it out together.