Behind the Scenes: Planning a 5-Month Solo Trip Step by Step

When people hear I’m planning five months of solo travel across the South Pacific and Southeast Asia, I often get the same reaction:

“Wow, that’s amazing! I could never do that.”

But this trip isn’t a vacation. It’s a lifeline.

My husband passed away suddenly this year. As I face the first winter without him, Christmas, New Year’s (his birthday), and the first anniversary of his death, I know the grief will come in waves…

🌊Tsunami-sized ones

So I made a conscious choice. 

I decided to escape winter and return to familiar places like my birth country, New Zealand…

Seek out some 😎 summer sun and beaches in Australia🦘…

And then head to Southeast Asia 🇹🇭 🇻🇳 for a combo of some soul-soothing and a blast of something new and exciting.

Right there is PRO TRAVEL TIP #1 👇

👁️ Making The Decision To Travel - Know Your Travel Vision

For me, this trip is part escape, part healing. 

It’s about reconnecting with people I love. 

Creating new memories... 

And giving myself space to reflect and grieve. Who knows what will come from that and that is the wonderful thing about traveling.

Not just discovering places but discovering yourself.

🌏 Planning 101 - Plan in Chunks of Time

The worst thing you can do is start to plan from the day your flight departs.

I plan in chunks…

How much time do I want to spend in 4 countries over 5 months?

Everyone has their own travel style.

When I travel for weeks or in this case months I don’t want to be bopping from place to place every couple of days…

Call it a form of slow travel a term that is rapidly becoming part of travel lingo.

So I started with time blocks, thinking in 4- to 6-week per location. 

That let me breathe room into the calendar and prioritize travel experience  over speed. 

My first chunk is visiting friends and family in New Zealand and Australia. It’s been five years, and it’s time. 

And honestly? I want to make the most of those golden summer days and stunning beaches given I’m escaping the Canadian winter.

Then I added in the two countries I had to cancel earlier this year: Thailand and Vietnam. 

Thailand has stolen my heart and this will be my third time returning and I want time there not just to explore, but to mourn and restore. 

Vietnam is new. A stretch. A challenge I’m ready for.

I always start with the why, then I plot it out on my calendar, like puzzle pieces.

It gives me a bird’s-eye view before diving into the logistics.

So bottom line start with the big picture.

📍 How I Actually Plan It All

Once I’ve blocked the destinations, I take into account two big things:

• Weather and seasonality
  
  

• Travel flow (i.e., is it actually doable?)
  

From there, I research flights and start mapping them on the calendar so I can figure out how long I need to move between places and what that means for my time and budget.

Flights are a big part of my budget.

I travel business class for long-haul flights, and for good reason: comfort, safety, and sleep matter when you're traveling this far, especially solo.

I also love the research process…

Google, YouTube, Facebook travel groups, talking to friends, they all help me shape what I might want to see and do in each location. 

But I don’t just fill the calendar with activities. I build in “downtime” and flex days. 

Because some of the best memories come from having space to wander.

I give thought to the energy of each place too.

🧘‍♀️Is this stop about rest (like a wellness retreat)?

🍱Is it about immersion in a culture, food, and city life?

🤓 My Not So Secret Weapon - Google Sheet or Excel

I have a custom-made Google Sheet that tracks everything:

• Calendar by destination
  
  

• Itinerary flow
  
  

• Budget
  
  

• Flight info
  
  

• Reservation links
  
  

It’s colour-coded, organized, and absolutely essential. 

I’ve tried other templates, but after two million frequent flyer miles, I’ve earned the right to say…

Mine’s the best. 😄

💰 Budgeting Like A Pro (With Room for Splurges)

I start with a ballpark figure, either what I want to spend or what I estimate based on past trips. 

Then I map out the “ideal” version… and start editing from there.

Do I really need that extra flight?

Can I downgrade the hotel to upgrade the flight?

What feels like value for me?

It’s a conversation in my head but it’s a fun one. 

FLIGHTS:

And… a reminder that I’m in charge of this experience.

📆 For business class flights, I scout prices early.

⏰ If it’s high season or a flight I really want, I book early. 

⏳ If it’s flexible, I wait and watch.

Reality check… you don’t often see Seat Sales for Business Class flights...

Or if you do they have multiple connections, long layovers, different airlines and sometimes even a mix of business and economy flights...

Which kind of defeats the purpose of arriving rested and relaxed at your destination.

This is more about managing expectations around your budget.

Short-haul flights? I’m savvy. 

I compare baggage fees, seat sales, and route times to make sure I’m not just saving dollars but making smart choices for solo travel comfort.

ACCOMMODATION:

Same with accommodations. If I’m booking a dream stay that doesn’t require full payment up front, I’ll secure it early.

If it’s a pay-now option, I may hold off and monitor availability. That helps me spread the budget spend across the months.

Even trains get added to the spreadsheet early. I note when bookings open (often 90 days out) and make a calendar reminder to grab tickets when the time is right.

ACTIVITIES:

PRO TRAVEL TIP! Likewise there are some activities that only open up bookings two or 3 months in advance i.e., Visiting the Anne Frank House in Amsterdam.

I get crunchy in my research to know what the ballpark costs of activities are going to be.

The over and above that I have a daily budget for food and other incidental expenses like getting an uber etc.

Another PRO TRAVEL TIP!

You will have sticker shock no matter what your initial travel plan looks like.

We’re human, we’re like kids in a candy store and we start out wanting to do and see everything because we think we may never back again.

Try to fight the”do it all urge” unless your budget and time allow for this option.

My best advice is “less is more”. If your one big thing visiting Spain is to get to the Alhambra then make it memorable.

Give yourself time to not only visit it but immerse yourself in it, maybe that includes a flex day so that you can go back a second time, or allow for getting up at the crack of dawn to have the place to yourself. 

🏔️ 🇳🇿I remember only too well visiting Mt Cook in New Zealand for a weekend with my husband.

I over heard a conversation from a tour group that had just arrived for THE NIGHT.

One lady said out loud… where are we and what’s this place about?

Clearly she was zoned out from hustling from one place to the next every day.

Even if you only have a week or two to travel you can still build in “slow travel” to create those lasting experiences.

Be Intentional About Your Travel Plans

This isn’t just about seeing new places. It’s about reclaiming something for myself in the midst of grief and change.

Yes, I’m planning a five-month trip. But what I’m really planning… is a gateway to a whole new world and life.

And if you’re reading this and wondering if you could ever do the same I hope you hear this loud and clear:

You don’t have to plan five months. You just have to take one brave step.

One destination. One calendar block. One choice that says yes to yourself!

I’ll be sharing more behind-the-scenes as I finalize accommodations, activities, and rituals I carry with me as a solo traveler. 

But for now this is how the dreaming begins.

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So cheers to wheels up to winging your way on your next travel building lasting memories.