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The Planning Thing

Updated: Sep 9, 2023

All photos taken by lotzacurls unless otherwise stated.

Selecting a destination for travel is difficult
Photo by wix.com

You’ve thought of a spot, your dream spot, the coolest place on Planet Earth. Congrats! Now you’re ready to start planning! But how??!?


Everyone’s got a different way to go about it, from meticulous planning to reckless spontaneity. Solo travelling gives you the flexibility to change your schedule as often as you’d like, but you might want to consider the following elements to ensure a stress-free (or close!) trip.


The original St. James' Gate Brewery in Dublin, Ireland
The original St. James' Gate Brewery in Dublin, Ireland

Choosing your destination

Basically, cost tends to be the primary deciding factor in choosing a travel destination. Keep in mind that countries that are far from yours might necessitate a more expensive flight, but be much cheaper than other countries once you’re there.


Lonely Planet divides most countries into three cost grades:

  • Top grade (where mostly everything is expensive) UK and Western Europe, Scandinavia, US, Canada, Japan, Australia and New Zealand

  • Middle grade (where some things might be less costly than others) Eastern Europe, Russia, most African countries, Singapore, Costa Rica, China and South Korea, and the Southern countries of South America like Chile, Argentina and Brazil

  • Lower grade (where everything is generally inexpensive) Southeast Asia, India and its subcontinent, Indonesia, most of Central America and northern South America

Camino de Santiago Spain
Wanna go on a long, soul-searching hike? Spain's Camino de Santiago might be your thing.

Here’s a breakdown of things you should consider as your departure date approaches:


Ten months before

Think and dream. Where have I always wanted to go, and why? What do I want out of this trip? Relaxing on a beach with a drink and a book? A wild animal safari? A booze-fueled party on a cruise ship? Do I want to zip like a whirlwind through 4 countries, or get to know one country really well? Can I afford to stay in hotels or BnBs, or would I rather rent a cabin on a beach or stay in a funky hostel? Are my travel documents even up to date?

What to do: Read guidebooks and magazines, and consult travel blogs. Consider whether you want to go on a cruise, join a tour group or explore a destination on your own. Lastly, make sure your passport won’t expire (and will be good for at least six months) by the time you intend on flying back home. Check your driver’s licence and bank card. Renew any relevant documents or cards.

Flying a trike (powered hang-gliding) with Paradise Air in O'ahu, Hawai'i.
Powered hang-gliding (trike) course with Paradise Air in O'ahu, Hawai'i. This is a once-in-a-lifetime experience! Photo provided by Paradise Air.

Eight months before

Travel is largely dictated by both time and money. Think honestly about your monetary budget and your time budget. Take a look at your work calendar. Also, consider the season in which you’ll be travelling (it’s generally good to avoid typhoon season in SouthEast Asia). How much time off could I possibly get? Can I have a satisfying visit in that amount of time? Can I realistically afford any of it?

What to do: See how feasible your dream vacation is with the amount of money and time you can allow yourself. Draw up pro/cons lists or make Venn diagrams - anything to figure it out.

Kayaking on a calm bay in Thailand
Kayaking in Thailand would have been a lot less fun during typhoon season.

Six months before

Time to start organising some logistics. Who do I need to consult at work in order to book time off? What vaccines or shots do I need? Can I stay in my current home, or do I need to pack up and book some storage space? Do I need a Visa or a travel permit? Are there any entry requirements? Will I need any immunisations? Will I be travelling in a loop and landing in/departing the same city? Or am I travelling from point to point and landing in/departing different cities?

What to do: Book time off work. Buy your return plane tickets. Consult your own country’s and your destination country’s government websites for any necessary Visas, travel permits or travel warning and make arrangements. (Every country requires a VISA to enter it; your country of origin - the one that has issued your passport - will determine whether or not you need one for that specific country. Visit VisaHQ.com to find out). You may need to prove that you’ve got sufficient funds in your account (a printout of your chequing account usually suffices) or show proof of your return flight (to guarantee that you’ll eventually leave the country). Pay bills in advance or arrange automatic payments. Book all appointments for immunisations (some vaccines have to be taken weeks/months before your trip, or need multiple shots with days/weeks between them). Make arrangements for bill payments, rent or storage. Start organising or delegating your commitments to work, family and pets.

Children playing in muddy water in Cambodia
Malaria pills are mandatory for a trip to Cambodia -- this stunning country should be on every adventure traveller's list.

Two months before

Now for some fun stuff. Where will I sleep when I arrive? Where will I sleep the night before I fly back home? What happens if I get sick and injured over there? Does my employer or my credit card offer health and travel benefits? How will I pay once I arrive at my destination? Will my bank cards work over there? Should I pay with my Visa or my bank card, or should I withdraw local currency? What happens if I lose my passport or cards while I’m travelling? What other places do I want to visit between landing and departing? And how many days do I want to spend at each place?

What to do: Book your first and your last nights’ accommodation. Purchase travel and health insurance and get to know your employer’s travel benefits. Learn how to access and exchange money and change any banking information (for instance, I had to get a travel VISA and change my PIN to four numbers instead of my usual six). Upload xe.com app. Make paper and digital copies of your passport, travel visas, Visa card and bank cards (if they get lost/stolen, the replacement process will be accelerated if you have copies on hand or in your inbox; entrust at least one person with digital copies). Make a rough itinerary of your trip using a calendar (ex: Places you want to visit and how many nights to spend at each place).

Camping on Iceland's famous Laugavegur hike
Sleeping in a tent in Iceland during our 3-day Laugavegur hike required more planning than a hotel, but it was oh so worth it!

One month before

Now for some really, really fun stuff. Where should I stay when I’m there? Do I want to spice it up and vary my types of accommodations? Are there any fun festivals, sporting events or public holiday celebrations? What mode of transportation should I use? Do I want to drive, and do I need an International Driver’s Licence?

What to do: Refine your itinerary so that you know where you’ll be sleeping every night (or keep things spontaneous!) Book your accommodations if you know your destination will be busy (ex: Florence in July or August). Search for upcoming events, as well as fun places to eat, drink and meet people. Book any train, boat or bus tickets if you can. Obtain an International Driver’s Licence if you think you’ll need it.

A HUMBLE SUGGESTION I like to read up on one country or one region, then choose a few central locations for my accommodations. Instead of moving from place to place every day or two, I stay in one area for several nights and make day trips over the next few days. That way, I can leave my heavy bag in my room (and my passport!) and travel light.
Kayaking Clayoquot Sound in Ucluelet/Tofino, BC Canada
Kayaking Clayoquot Sound in Ucluelet/Tofino, BC Canada

The week before

The countdown is on! What items should I pack? What type of baggage should I bring? What kind of weather will I run into over there? Do I need to bring medication? How will I use my phone? How will I charge my devices? How am I getting to the airport?


What to do: Make a list of the items you’ll need: passports and travel documents, clothing and footwear, technology, memory cards and chargers, toiletries, medications, traveller’s First Aid (painkillers, antihistamines, bandages, anti-diarrhea, and something for sunburns), etc. Get any prescription medicines filled out. Print (or screenshot) all airline tickets, bookings, train/bus tickets, special events tickets, etc. Check your phone company’s fees or look into getting a cheap Sim card abroad. Find out if you’ll need an adapter and what voltage to use; buy a universal travel adapter if needed. Plan your transportation to/from your home and airport.

This will help: Read The Packing Thing

Dead Horse Point State Park Moab Utah USA
Thankful for my wool tuque and puffy jacket. Overlooking Dead Horse Point State Park, Moab (Utah)

The night before

I’m so excited, I can’t think straight!

What to do: Charge your devices then pack chargers. Delete old photos to make space for new ones. Print (or screenshot) tomorrow’s airline ticket. Unplug electronics, turn off the AC/turn down heating, turn off water. Clean out your fridge of anything that might rot during your absence. Take out the trash/compost. Water your plants.

Hiking the Alpe di Siusi, Italian Dolomites Italy
Hiking the Alpe di Siusi in the Italian Dolomites

So there you have it! Enjoy your trip, you've earned this time off and you've done just about all you can to make it as smooth and hiccup-free as possible.


See you out there!


Other articles you might enjoy:

The Arrival Thing


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