How I create my itineraries.
I love making travel itineraries.
Piecing together arrival times, budget, drive time, and lodging—I find it all deeply satisfying.
In traveling, I believe detailed planning is the steady foundation that allows spontaneity to spark. You can take that scenic route and enjoy that spontaneous hike to the ocean, but a seasoned traveler knows we have to jump back in the car by at least 6pm to make it to the Airbnb by check-in time at 10.
You have your fun, but you also have a place to lay your head come nightfall. It’s the best of both worlds.
Here’s how I like to plan my traveling:
Start with the set of days I have available to be gone and refer to them as: day 1: the 31st, day 2: the 1st, and so on
Most important date here is when I have to be home to be back at work or for any other obligation.
Determine the nonnegotiables, if any
For example, I’m planning on attending a concert on Friday, the 30th and can’t change that, so I'll plan my more flexible events around that date.
Determine touch points along the trip
Is there anywhere between home and my final destination I’d like to visit? Are there friends in cities along the way that I can touch base with? If possible, I’ll make mini stays there—sleep for a night or plan to have a meal in one of these places.
Research, research, research
Reading the reviews of Airbnb have saved my life on more than one occasion. I look deep into the places I’m contemplating staying whether they’re hotels, hostels, or Airbnbs. Even if I’m not planning on lounging around the lodging space, it’s still the environment I’m paying to rest in. It’s important that it feels restful.
Use a single note or sheet of paper to divide up the days, determine the touch points, track travel times, and calculate lodging, gas, and food costs
Once I piece together the details, my plans look something like this:
PNW Trip - requested off 27th to 31st
Thursday - DAY 1 - 28th
Sacramento to Portland (9.5 hours)
SLEEP - Society Hotel - private room: $128
Friday - DAY 2 - 29th
Portland to Spokane (6 hours)
CONCERT at 6pm
SLEEP - Spokane - Airbnb: $143
Saturday - DAY 3 - 30th
Spokane to Medford (10 hours)
SLEEP - Medford - Airbnb - 2 nights minimum: $470
SUNDAY - DAY 4 - MEDFORD - 31st
SLEEP - MEDFORD
MONDAY - DAY 5 - 1st
Medford - Sacramento (5.5 hours)
Rough totals:
$741 total for lodging.
$500 gas.
$200 food.
= $1441
From here, I can determine if that number is outside what I’m comfortable spending and adjust lodging or the number of travel days from there.
After I have this skeleton of an itinerary and the days are set, I can consider my options in exploring the places I’ll be on the days I’ve determined. For example, I’ll likely grab breakfast the morning of Friday, the 29th before I start my drive up to Spokane. Let’s look into great breakfast places in the Portland area!
6. Determine possible surrounding costs
Lastly, I find it important to consider surrounding costs. If traveling by car—will I need an oil change, tire rotation, or any necessary repairs to ensure I’ll get to my destination in one piece? If traveling by air—will I need a new suitcase or budget for Uber/taxis/trains once I make it to my destination?
In all, I’ve found it rewarding planning my itineraries in a green light mode manner right off the bat. It’s helpful for me to let myself plan the trip I want first, and if it proves to be outside my budget, I can cut corners or adjust details to make it a trip I can afford.