Whenever I’m getting ready to travel—especially internationally—I follow the same routine in the days before departure. This process helps me stay organized, earn extra travel points, and start my trip feeling calm instead of stressed.
This isn’t about packing. This is the final trip preparation I do a few days before leaving to make sure everything runs smoothly once I arrive.
Here’s my step-by-step pre-trip routine. Prefer watching instead of reading? Watch the full video here: https://youtu.be/BDM8lKKiRjQ
1. Map Out the Entire Trip on Paper First
The first thing I do is pull out my old-fashioned paper calendar.
This is where I write down everything:
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Flight arrival and departure times
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Hotel stays
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Train schedules
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Tours and activities
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Transportation details
Seeing everything laid out in one place helps me visualize the flow of the trip. I can quickly spot conflicts, gaps in the schedule, or days where we might be trying to do too much.
That said, I don’t actually want to carry that paper calendar with me while traveling. It’s just my planning tool before the trip.
2. Book Tours Through Platforms That Earn Points
When I book tours, I typically use platforms like:
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Viator
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GetYourGuide
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Airbnb Experiences
Which one I choose often depends on the activity—but it also depends on the points I can earn through Rakuten.
Sometimes Rakuten offers 10x to 15x points when booking through certain travel platforms. That means if you spend $100 on a tour, you could earn 1,000–1,500 points toward future travel.
To maximize this strategy, I always make sure to:
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Start my booking through Rakuten
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Use the right travel credit card when checking out
This strategy is often called double dipping or even triple dipping—earning points from multiple sources for the same purchase.
3. Take Advantage of “Pay Later” Flexibility
One thing I love about booking tours through these platforms is the pay later option.
Many tours allow you to reserve your spot but delay payment until closer to the tour date.
This gives you flexibility because:
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You can lock in a popular tour early
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You still earn Rakuten points
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You can cancel up to 24 hours before the tour in many cases
Travel plans change, and flexibility is always valuable.
4. Review the Itinerary With Your Travel Partner
If I’m traveling with someone else—whether it’s a friend or one of my kids—I go over the itinerary with them before we leave.
We ask questions like:
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Are we still excited about these tours?
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Does the timing still make sense?
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Do we want to add something new?
Sometimes the vibe changes, and that’s okay. Travel should feel fun, not rigid.
5. Balance Structured Activities With Free Time
On most trips, I like to book one or two tours depending on the length of the trip.
These might include:
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Day trips outside the city
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Walking tours
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Cooking classes
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Cocktail experiences
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Ghost or paranormal tours
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Cultural or historical tours
I especially enjoy evening tours, which can offer unique experiences you might not find during the day.
But I’m careful not to overschedule.
If I book two tours in one day—maybe a mid-morning tour and an evening experience—I always leave the middle of the day open.
That time is perfect for:
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wandering the city
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finding a local café
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shopping
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relaxing
Sometimes the best travel moments happen when you leave space for spontaneity.
6. Move Everything Into My Digital Calendar
Once the itinerary feels right, I transfer everything into my iPhone calendar.
This makes it easy to access when I’m on the go.
Another option is using a service like TripIt, which can automatically organize your travel confirmations in one place.
The key is making sure your itinerary is set to the correct time zone, so everything displays accurately once you arrive.
A small but important tip:
Always include the reservation or tour confirmation number in the calendar entry.
7. Confirm the First Few Days of Activities
A few days before departure, I double-check the first two days of activities.
At this point I will:
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Confirm reservations
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Make any remaining payments
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Download tickets or confirmations
You never know what Wi-Fi will be like when you arrive. I don’t want to be standing on a street corner trying to find an email or figure out where the meeting point is.
The first couple of days should feel easy and stress-free.
8. Organize Important Documents in a Travel Folder
Before leaving, I also prepare a small travel folder that stays in my carry-on.
Inside I keep things like:
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hotel confirmations
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transportation details
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tour information
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key reservation numbers
Once I arrive, I don’t carry this folder around—but it’s extremely helpful during travel days.
One important rule:
Never put important documents in a checked bag.
If your luggage gets lost, you don’t want to lose access to critical information.
9. Set Up My Jet Lag Strategy
If I’m traveling internationally, this is also when I set up the TimeShifter app.
TimeShifter helps you adjust your sleep schedule before and during travel so you can minimize jet lag.
I’ll actually be demonstrating how this works on an upcoming trip to Spain, because it can make a big difference in how quickly you adjust to a new time zone.
Final Thoughts
This simple pre-trip routine helps ensure that the start of my trip feels organized and stress-free.
Once everything is confirmed and organized, then it’s time to start packing.
If you’d like this routine in checklist form, or if you have favorite travel apps you love to use, let me know in the comments.
And if you find this content helpful, make sure to subscribe, share, and give the video a thumbs up.
Until next time — blue skies.
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