How I Plan a Trip: From “Where Should We Go Next?” to “It’s On the Calendar!”
People sometimes ask me how I decide where to go next.
The short answer?
I start with a list.
Not exactly breaking news.
I usually have several destinations floating around in my head — places I’ve wanted to visit for years, places I recently discovered, or places that simply sound interesting.
But wanting to go somewhere and actually putting it on the calendar are two very different things.
Before I book anything, I do some digging.
Because while I love an adventure, I do not particularly enjoy being flooded, frozen, baked, financially assaulted, or surrounded by 40,000 of my closest tourist friends.
Here’s how I turn “Where should we go next?” into “It’s on the calendar!”
- I Start With My Wish List
Sometimes I know exactly where I want to go. Other times, I compare a few possibilities based on time, budget, location, and what has been calling my name.
Because I always seem to have more places I want to visit than calendar space and coins, I keep a running travel wish list.
I’ve created a What’s Next on Your List? Travel Wish List you can download for your own “someday” destinations — because “someday” has a better chance of happening once you put it on a list.
- I Look for the Sweet Spot
One of the first things I research is when to go.
My goal:
Better prices. Fewer crowds. Decent weather.
I want to save money without arriving during monsoon season, a blizzard, or temperatures that make me question every decision that brought me there.
Weather, holidays, school breaks, and peak travel seasons all matter. Sometimes moving a trip by just a week or two can make a big difference.
- I Compare Flights, Hotels — and Rewards
Once I have a destination and general time frame, I compare flights and lodging using Expedia, Google, airline websites, hotel websites, and other travel platforms.
Before paying cash, I also check airline miles, hotel points, credit card rewards, and travel credits.
The lowest advertised price isn’t always the best deal.
A slightly more expensive flight may save hours of travel time. A pricier hotel may cost very little after points are applied.
I look at the whole trip, not just the number on the screen.
- I Look at the TRUE Cost of the Hotel
A cheaper hotel is not always the cheaper choice.
If it’s far from everything I want to see, I may spend the savings on gas, parking, taxis, or ride-shares just getting from Point A to Point B.
Sometimes paying a little more for the right location saves money, time, and frustration.
I’m not looking for the cheapest trip.
I’m looking for the best overall value.
- I Figure Out How We’re Getting Around
Will we need a rental car? Can we walk? Is public transportation convenient? Are ride-shares easy to find?
Transportation can completely change the cost and feel of a trip.
And if we’re traveling internationally, I also want to know whether renting a car means driving on the other side of the road.
Been there. Done that. Survived.
- I Make the Activity List — Then Edit It
Once I start researching, suddenly I want to do everything.
So I divide activities into three categories:
Must Do — I’d regret missing it.
Would Love to Do — if time and coins allow.
Bonus — great if it works out.
That keeps the itinerary from becoming a military operation.
- I Estimate the REAL Cost
Flights and hotels are only part of the budget.
I also consider transportation, meals, activities, tips, baggage fees, parking, resort fees, insurance, and the inevitable “while we’re here…” expense.
I don’t need an exact number down to the penny. I just want a realistic idea of what the trip will actually cost before I commit.
- I Leave Room to Wander and Breathe
I used to think a successful trip meant seeing as much as humanly possible.
Now I deliberately leave open time.
Some of my favorite moments have happened when nothing was scheduled — wandering through a neighborhood, finding a little restaurant, hearing music, talking to someone local, or changing plans because somebody suggested something better.
There needs to be room for the trip to surprise you.
- I Keep a Plan B
Weather happens. Flights get delayed. Excursions get canceled. People get tired.
I keep a few backup ideas without trying to plan for every possible disaster.
Flexibility makes travel much less stressful.
- Then I Book It
Eventually, research has to turn into action.
Once the dates, flights, lodging, transportation, and overall cost make sense, I book the trip.
And there’s something very satisfying about moving from:
“We should go there someday.”
to
“It’s on the calendar!”
Of course, that’s usually when I start thinking about the next trip. 😉
Don’t Plan the Life Out of the Trip
After all the searches, reviews, maps, points, reservations, and confirmation numbers, I try to remember one thing:
Don’t plan the life out of the trip.
Do enough research to travel confidently and book enough to avoid unnecessary stress.
But leave room to wander, change your mind, talk to people, and experience something you never could have planned.
Because sometimes the best part of the trip isn’t on the itinerary at all.
There are plenty of little things I check before I hit Book — weather, hotel location, transportation, points and miles, fees, cancellation policies, activities, and the real trip budget.
Rather than make this blog 17 pages long, I’ve put those details into a Next On the List Trip Planning Worksheet you can use for your own trip.
🎵 Soundtrack of the Story
This Week’s Song:
Three Little Birds — Jacob Collier
Why It Matters:
Travel planning is exciting, but it can also become a rabbit hole of prices, schedules, reviews, weather forecasts, points, miles, and about 18 open browser tabs.
At some point, you have to do the research, make the best decision you can, and trust that everything doesn’t have to be perfectly figured out before you go.
That’s why Three Little Birds feels right for this story.
Plan smart. Leave room to wander and breathe. And when the inevitable travel gremlin shows up, remember: most things can be adjusted, rerouted, rebooked, or simply turned into another story.
Sometimes you just have to put it on the calendar and go.
