Charting our course

Sunset in Big Pine Key, FL - during one of our first big road trips in 2020.

Wondering how we planned our incredible cross-country road trip? In this blog post, I’ll take you behind the scenes and share how we planned our travels. From collecting destination ideas, to optimizing our route for efficiency and balancing work commitments, let’s dive in.

Dreaming big but staying grounded

Our travel wish list was a compilation of years of inspiration gathered from various sources. Whether it was recommendations from friends, captivating scenes from movies, the allure of the U.S. National Parks, or simply the need to cross a given state off my list, we had a vast collection of places we couldn’t wait to explore. Brainstorming our long list was an exciting starting point, but then came the hard work of paring back the list to eliminate any destinations that were too far out of the way or just didn’t actually seem that worthwhile upon further research. YouTube was a helpful resource to sense for the vibe and scenery of different National Parks and towns across the country. 

Route efficiency and weather considerations

With our list in hand, we faced the task of mapping a route to visit as many locations as possible within our timeframe of 4 months. Aware that we would be embarking on our journey in March and ending in July, we anchored to catching the tail end of ski season in Colorado, then headed southward. By prioritizing warmer regions (like Southern Utah and Palm Springs) during the early months and gradually heading north, we’ve been able to make the most of the outdoor recreation opportunities at each destination. (However, given the historic snowfall out West this year, there were still a few destinations we couldn’t visit due to road closures – like in Sequoia, Crater Lake, and Mt. Rainer National Parks.) 

Balancing work and exploration

As digital nomads, we knew that our journey would involve juggling work responsibilities alongside our travel adventures. To ensure a smooth workflow, we aimed to minimize driving time during the weekdays. This meant strategically planning our stays in different locations to allow for ample time to dive into the local culture, check out all the best restaurants, and immerse ourselves in the natural scenery. Of course, you can only do your best to plan – so far it has been a delicate balancing act requiring flexibility, adaptability, and a commitment to making the most of every moment.

Easing into life on the road

To ease ourselves into the nomadic lifestyle, we strategically structured our itinerary. At the beginning of our trip, we planned for longer stays in each location, but as the journey has progressed, we’ve transitioned to shorter stays in each place. This gradual shift helped us acclimate to the constant movement, while also ensuring we had ample time to explore the must-see attractions in the early stages of our adventure.

Optimizing comfort and budget

While it’s been important to have a comfortable place to stay and work at each destination, we’ve been very mindful of minimizing our lodging expenses to leave room in the budget for experiencing each stop to the fullest. With this in mind, we took a proactive approach to booking our stays. Knowing that popular destinations tend to have limited availability and higher prices, we started by booking accommodations for locations that either had fewer lodging options or were in high demand. This allowed us to secure the best selection of affordable Airbnb rentals or hotels that aligned with our budget.

Staying organized – the master Excel doc

To keep track of our itinerary, lodging bookings, and expenses, we created a master road trip document in Excel. This tool helped us visualize our journey, map out our daily destinations, and stay on-budget throughout the trip. If you’re interested in seeing a copy of my Road Trip Planner doc, send me a message and I’d be happy to share!

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