Sample Itineraries
Every itinerary on this page is based on a real trip I've planned and experienced myself.
Every trip is different. Some are built around hiking, cycling, national parks, or races. Others focus on cities, local food, history, or simply slowing down and exploring.
These examples show how I organize information and what a finished itinerary can look like.
Pacific Northwest Fall Road Trip
9 days • Oregon, Northern California & Washington • ~1,000 miles
This was my fourth trip to Oregon and one of the itineraries that best represents how I like to travel.
The route connects the Oregon Coast, Redwoods, Cascades, Painted Hills, and Mount Adams into a trip that balances scenic drives, memorable hikes, local food, and enough flexibility to enjoy the places you didn't expect to love.
One thing you'll notice throughout my itineraries is that I usually include more options than anyone could realistically fit into a single trip. That's intentional. I'd rather build in flexibility than discover something amazing after it's too late to adjust the plan.
To me, the route is just as important as the destinations. The roads you choose, where you stop for lunch, when you start the day, and how the trip flows all shape the experience. That's the idea behind The Thoughtful Route.
Here’s what the finished itinerary for this trip looked like.
Moab Adventure Week
7 Days • Moab, Utah
This trip required more planning than most.
I spent a lot of time researching hikes, mountain biking trails, scenic drives, and national parks to build an itinerary that made the most of six days without feeling rushed. It pushed me outside my comfort zone more than once, and that's part of what made the trip so memorable.
Some experiences required more than simply showing up. One hike involved a permit and a ranger orientation before setting foot on the trail. The trip was also timed around a new moon so I could experience some of the darkest night skies in the country at Utah's International Dark Sky Parks.
Not everything was planned, though. One of my favorite evenings came from stumbling across live music after a day of exploring. That's one of the reasons I like building flexibility into my itineraries. It leaves room for the unexpected.
Here's what the finished itinerary for this trip looked like.
Valladolid & Puerto Morelos
8 days • Yucatán Peninsula, Mexico
This itinerary grew out of several work trips to Mexico. After the conference ended, I used the weekend to explore the Yucatán with family, making the most of a few days before flying home.
Planning for a group is different than planning for myself. The itinerary balanced history, local food, cenotes, beach time, and enough flexibility for everyone to enjoy the trip at their own pace. My goal was to make the most of a short trip without making it feel rushed.
One of the things I enjoy most about planning is bringing together different interests into a trip that everyone enjoys. That's become especially rewarding as friends and family have started asking me to plan their travels.
Here's what the finished itinerary for this trip looked like.
Erie Canal Gravel Cycling Adventure
5 Days • New York • ~365 Miles • Gravel Cycling
This itinerary was a little different than the others.
The ride was planned by the leader of our cycling group. After he was injured the week before the trip, I volunteered to help with some of the logistics. I verified restaurant hours, made a few adjustments where plans no longer fit, and organized everything into a field-ready itinerary that was easier for the group to use throughout the ride.
It was a small contribution to a much larger trip, but it reinforced something I've learned over the years. Sometimes the biggest value isn't creating the plan. It's organizing the details so everyone else can simply enjoy the experience.
Here's what the finished itinerary for this trip looked like.
Ready to Start Planning?
Tell me a little about the trip you have in mind. Once I review your responses, I'll reach out and we'll take it from there.