People often ask how we’re able to plan trips to places like Iceland, Madeira, Costa Rica, Norway, Greece, and the Dolomites without spending months researching every detail.
The truth is that we don’t try to plan everything at once.
That’s the fastest path to feeling overwhelmed. And travel planning can be overwelming. There is more information than ever before online and it can take a long time to search through it all.
Instead, we’ve developed a simple process that breaks a big international trip into manageable pieces. Whether you’re planning a week in Iceland or a month in Europe, this is the exact framework we use.
This week paid subscribers can download my International Trip Planner - this 4 page workbook makes it easy to plan your next trip. Scroll to the end of this newsletter for the printable.
Paid subscribers also get my itinerary plan - you can download this to print OR edit it in Canva.
Step 1: Pick the Adventure, Not the Destination
Most people start by asking: “Where should we go?”
We start by asking: “What kind of adventure do we want?”
Do we want:
Epic hiking?
Road trips?
Wildlife?
Beaches?
Culture and food?
A mix of everything?
Once you know the experience you’re looking for, the destination often becomes more obvious.
For example:
Want dramatic hiking and mountain scenery?
→ Madeira, Norway, or the Dolomites.
Want adventure plus wildlife?
→ Costa Rica.
Want landscapes that feel completely different from anywhere else?
→ Iceland.
The destination should support the experience, not the other way around.
Step 2: Build the Skeleton of the Trip
Before booking anything, we create a rough framework.
We answer three questions:
How many days do we have?
What are the 3–5 experiences we absolutely don’t want to miss?
How much driving or moving around do we actually want to do?
That’s it.
No hotels.
No restaurant reservations.
No hour-by-hour itinerary.
Just the big pieces.
For Iceland, that might be:
Glacier hike
Waterfalls
Black sand beaches
Ice lagoon
For Madeira:
Pico do Arieiro sunrise
Levada hikes
Coastal viewpoints
Funchal
Everything else gets built around those anchors.
Step 3: Find an Existing Itinerary
One of the biggest mistakes travelers make is trying to reinvent the wheel.
Whenever we’re visiting somewhere new, we start by looking at sample itineraries.
Not because we follow them exactly.
Because they help us understand:
How far things are apart
What works together geographically
How many days are realistic
Some of our most popular itinerary resources include:
Use existing itineraries as a starting point, not a rulebook.
Step 4: Book the Important Stuff First
There are only a few things we prioritize booking early:
Rental cars
Popular accommodations
Everything else can usually wait.
Trying to reserve every restaurant and every activity months in advance only adds stress.
The goal is to secure the things that could derail the trip if they sell out. I usually research these for a day or two to compare overall budgets - THEN I book them all at once.
I’ve broken down how to do this (and some tips on saving money on each step)
Step 5: Leave Space for Discovery
This is the step that changed how we travel. Earlier trips we either planned down to the hour or left it open.
Now we intentionally leave open space but not the whole day.
Some of our favorite travel memories happened because we:
Took a random side road
Stopped at a viewpoint
Followed a local recommendation
Spent longer somewhere than expected
A great itinerary creates opportunities. Maybe you have a few ideas jotted down in case there is time.
Step 6: Save Everything in One Place
We keep:
Flight confirmations
Hotel reservations
Rental car information
Tour bookings
Maps
Notes
In a single location.
The less time spent hunting through emails while traveling, the better.
Simple systems make trips feel easier.
I usually create a spreadsheet to keep track as I’m booking things but then I put it all into an itinerary.
Paid subscribers can download an itinerary planner template or get one you can edit in Canva at the bottom of this newsletter.
The Biggest Planning Mistake We See
Most people try to plan an entire trip at once.
Instead, focus on one decision at a time:
Pick the experience.
Choose the destination.
Build the framework.
Find sample itineraries.
Book the essentials.
Leave room for adventure.
That’s it. The goal isn’t to create the perfect itinerary.
The goal is to create a trip you’re excited to take.
If you have more than 1 destination you can link these together.
Resources to Help You Plan
If you’re looking for inspiration for your next international adventure, these guides are a good place to start:
Madeira — Mountain ridges, levada hikes, coastal views, and one of our favorite hiking destinations in the world. → Read our Madeira guides
Iceland — Glaciers, waterfalls, volcanoes, and road trips through some of the most unique landscapes on Earth. → Explore Iceland
Search More International Destinations
This week paid subscribers can download my International Trip Planner - this 4 page workbook makes it easy to plan your next trip. Scroll to the end of this newsletter for the printable.
Paid subscribers also get my itinerary plan - you can download this to print OR edit it in Canva.
