Travel-n-Trips

Family Gap Year Post #10: Departure To Do List

Family Gap Year Departure To Do List

I started writing posts about planning a Family Gap Year back in September of 2019. And then everything came to a grinding halt in March 2020.

And here we are in March 2022 and it looks like things are on track for a June departure!?!?

Everything is all set for me to work remotely for the year. We are moving our current CFO/COO into the Executive Director of Magnolia Montessori For All (the school), and I will stay as the CEO of Montessori For All (the national non-profit organization) without also focusing on the school like I have been doing. This transition is not connected to my trip, but it definitely makes working remotely much, much easier.

The first part of the trip (June and July) is very planned out with all of the AirBnbs booked:

June

Epic Road Trip: Austin to Bloomington to Madison to Livingston (Montana) to Baring (Washington) to Vancouver to Eugene (Oregon) to Arcata (California) to Stinson Beach to San Francisco to Los Angeles to Pasadena. We finish that portion of the trip in early July. Then it’s off to Hawai’i.

July

Hawai’i:

  • 10 days in Oahu
  • 7 days in Kaua’i with dear friends
  • 7 days in Maui with a different set of friends (glamping on the beach)

August through October

We will settle into Hilo on the Big Island.

November

We will travel to Malaysia for a wedding and then spend two or so weeks in Bali.

December

We will fly into Melbourne, Australia, and drive up the coast to Sydney and then Byron Bay.

January

We will hopefully fly into New Zealand and do a road trip around the South Island for a month or so.

February through June

We will settle outside of Wellington.

It’s impossible to have a 100% settled plan at this point. I’m honestly shifting my thinking away from the trip planning and more toward planning our departure. There’s so much to do!

Family Gap Year Departure To Do List

  1. Get physicals for everyone
  2. Look into the vaccination situation
  3. Go to the dentist
  4. Sell one of our cars
  5. Get professional photos of our house
  6. List our house for rent
  7. Finalize our packing lists
  8. Make a plan for homeschooling our boys
  9. Write birthday cards in advance for the whole year we are gone
  10. Make our budget
  11. Purchase travel insurance
  12. Check on our passport situation
  13. Figure out a plan for our medications
  14. Withdraw our boys from school with an official intent to homeschool

What am I missing from my Family Gap Year Departure To Do List? That list doesn’t actually sound as scary as I thought it would be. I must be missing something?

6 Comments

  • Stacy

    I’m so excited to continue to follow your adventure. have 2 things you may have already thought about, but figured I’d mention them in case! First, a plan for cell phones and service while outside of the US. Second, will you or Matt be earning any money in Australia or New Zealand (eg, photography gigs)? If so, looking into the logistics of taxes, contributing to US retirement accounts, etc.

  • Jennifer

    As a fellow traveler, I would recommend checking out Google Fi for cell service at a reasonable price that has international coverage. For trip insurance, I would recommend checking out World Nomads.

  • Nanci

    Wow, that is fine funny – I used to live in both Hilo & Wellington. What made you choose those places?

    Weee you at the AMS Conference in Nashville? I didn’t realize the Monarch Readers listed in the exhibits was from your school – I would have stopped by to meet you….

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