Secrets to Planning the Perfect Road Trip

An All Roads North trip includes many visible elements—wonderful accommodations, thoughtfully curated experiences, and seamless organization are all expected. However, there are subtler aspects at play, the “dark arts” of trip design, if you will, that often go unnoticed. These imperceptible tweaks, intricate details, and strategic insights have been honed by our Destination Specialists over years of experience. Here are a few of the hidden elements we’ve discovered are essential to planning the perfect road trip.

1. Less is more. If we had a single trip design mantra, this would be it. It is so tempting to try and fit in as much as possible but focusing on fewer places across a smaller area will give you the time to slow down and connect with the places you visit. 

2. Leave room for the unexpected. One of the great joys of travel is the excitement of the unknown, those serendipitous moments that can’t be planned and never follow the script. Rather than schedule every moment of every day, we intentionally leave space for those moments to happen. 

  

The Tide-To-Table culinary experience at Nimmo Bay Wilderness Resort | Mackenzie Sound, BC Canada 

3. Three is the magic number. We always try to have at least a few three night stays in our favorite places. This allows for the first day to get the lay of the land and cover the ‘must sees’, with a second day to get off the beaten path, indulge a particular passion or try a new experience.

4. Days of the week matter. Whether avoiding Yosemite Valley on a summer’s weekend, catching some Saturday morning Zydeco in Cajun Country or Monday night clambakes on Nantucket, carefully structuring itineraries so that certain places fall over certain days of the week will add to the experience. 

   

The many majestic views of Under Canvas Lake Powell – Grand Staircase.

5. It’s a family affair. Whether you’re traveling as a couple or a multi-generational family, one person is usually the designated ‘planner’ but we’ve found that getting as many of the group involved in the early planning process, allowing them to share their own ‘wish list’ and to help shape the final itinerary, only helps add to the anticipation and excitement.

6. It’s the people you remember. It is typically not the award-winning luxury hotel or even the magnificent national park that clients remember most, but rather a person that they spent time with. This is why we see connecting our clients with the best local experts, guides and insiders as the most important part of our job. 

      

The Llama breakfast trek and scenic Yellowstone River boat tour | Sage Lodge, Montana

7. Burn the bucket list. Well maybe not all of it, but the trouble with bucket lists is that everyone else reads the same articles or follows the same Instagram influencers and has a very similar looking list. Try to include a few places and experiences that everyone else isn’t shouting about, it will make that sense of discovery all the sweeter.

8. End on a high. Psychologists have noticed that people remember the beginning and end of an experience more than the middle. Ending a trip on a high at a fantastic property or with a memorable experience provides the perfect cognitive fireworks to remember the road trip by.

Sheldon Chalet

The deep seclusion of Sheldon Chalet | Denali National Park, Alaska

SUBSCRIBE TO OUR NEWSLETTER

  • By entering your information you agree to receive emails in accordance with our Privacy Policy
  • This field is for validation purposes and should be left unchanged.



Curious to learn more?

For national park profiles, insider interviews, hidden gems and more, subscribe to our bimonthly newsletter