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 minute call, plus a 30 minute follow up call
A practical, judgment free session focused on your finances and how travel fits into them. We look at your income, fixed expenses, and spending patterns to build a realistic monthly budget, then figure out exactly how travel can live inside it. The follow up call is built in so we can check in after you've had time to put the plan into practice, adjust what isn't working, and make sure you're actually making progress toward the trip you want.
What’s included
60 to 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 fly business and first class internationally, book luxury hotels, and cut the cost of trips significantly. This session shows you how to do the same.
What’s included
Delivered within 7 to 14 days, includes a 30 minute walkthrough call
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
Pricing by trip length: 1 to 4 days, $175. 5 to 8 days, $225. 9 to 13 days, $300. 14 or more days, $375.
Performance based · $75 minimum
Most people sit on points they don't know how to use. This is different from our card strategy session, you don't need to worry about the complex transfers. We're not here to talk about which cards to get or how to earn more. We're here to take what you already have and turn it into a real booking. We identify the best available redemption for your trip, handle the full transfer from your account to the airline or hotel program, and confirm the booking on your behalf.
What’s included
Our fee is 15% of what you save compared to the cash price of the same seat or room. The $75 minimum applies to smaller redemptions. If the savings don't justify it, we'll tell you upfront.
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 and 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.
The points strategy session is about the long game — which cards to get, how to earn more, and how to think about redemptions. The points transfer service is purely execution. You already have points, you have a trip in mind, and you want us to find the best redemption and handle the booking for you. If you're not sure which one fits, just tell us where you are in the form and we'll point you in the right direction.
Our fee is 15% of what you save compared to the cash price of the same seat or room, with a $75 minimum. We give you a savings estimate before you commit, so you'll know exactly what to expect. If the math doesn't make sense for your situation, we'll tell you upfront.
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.
Pricing is based on trip length: $175 for 1 to 4 days, $225 for 5 to 8 days, $300 for 9 to 13 days, and $375 for 14 or more days. Every itinerary includes a 30 minute walkthrough call once it's delivered so you can ask questions and make sure it actually fits how you travel.
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.
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 2 business days. 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.