Planning can be stressful for some humans, but for me, it takes the stress out of traveling. I can let loose and have fun on my trips because I know I’ve thought of everything.
Here's a chronological (what else would you expect?) run down of what I like to plan in the weeks and months before my trips.
6 MONTHS
- Do cursory research of your destination to find out if there are any tours or places you want to stay that require advanced booking e.g. Incan Trail.
- Check seasonal weather, high season pricing, and regional holidays/festivals in order to pick your dates.
3 MONTHS
- Buy flights.
- Apply for visas if necessary.
2 MONTHS
- Book hotel/hostels. I highly recommend Booking.com for their free cancellations and no deposits.
- Check the CDC website to see if you need any vaccinations; if so, make doctor’s appointment to get them.
1 MONTH
- Make reservations with any fancy restaurants you want to try.
- Book any tours or excursions you’d like to take.
3 WEEKS
- Prepack and make a list of the items you are missing (see my packing guides).
- Purchase those items in store or online.
- Fill your travel toiletries at home instead of buying new ones.
2 WEEKS
- Start your travel binder! (or wherever you keep your important documents when you travel)
- Print reservation confirmations, maps, directions, etc. Stay organized!
1 WEEK
- Pack! You know that feeling when you are at the airport and you remember something you forgot to pack? If you back a week before, that feeling will hit you in your living room! Crisis averted.
- Download any movies or TV shows for your long flight (get free downloads of movies and shows with Amazon Prime Video)
- Download any travel apps you might need e.g. your airline’s app, maps.me etc (See my tech guide.)
24 HOURS
- Check into your flight and print your boarding pass, add it to your binder.
- If you don't have automatic check-in on your return flight, set a reminder on your phone to check in 24 hours before your flight home. You'll be having too much fun to remember!
- Open your luggage and take a good hard look at what you’ve packed–and take out that thing you know you’ll never wear!
- Charge your devices and don’t forget to pack the chargers! (Or just keep an all-in-one travel charger in your bag so you are never without the right cord.)
- Lay out your travel clothes if you are leaving early in the morning, sleepy you will thank you.
If you follow this planning calendar, you’ll never be ill-prepared again. Planning can be stressful for some humans, but for me, it takes the stress out of traveling. I can let loose and have fun on my trips because I know I’ve thought of everything.

Are you a planner or do you prefer to figure it out when you get there?
Let me know in the comments.
Go confidently travelers!
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