Hitting midlife often brings a longing for adventure and the freedom to explore the world. Whether it’s a month-long escape to Europe, a trek through Southeast Asia, or a quiet retreat in the Caribbean, preparing for an extended journey requires thoughtful planning. From making sure your home is secure and insurance-compliant, to managing health considerations and understanding customs regulations – there’s a lot to think about when planning a long trip.
Here is a mini-guide with tips to consider before embarking upon on a long journey.
Table of Contents
1. Travel Documents & Border Entry
Passport: It needs to be valid for at least six months beyond your planned return. Many countries are strict about this, and the last thing you want is to be turned away at the border. For more details, you can always check Travel.gc.ca.
Visas and eTAs: Check the requirements. I remember visiting Singapore years ago when it was visa-on-arrival, but by 2023, it had transitioned to an eTA process. It’s crucial to check each country on your route. Some require transit visas too. Check what type of visa you will need if you plan to stay for longer than the duration allowed under the visa-on-arrival or ETA. Can you exit and re-enter to extend the visa? Check the formalities.

International Driving Permit: If you plan to drive abroad, make sure to grab an International Driving Permit. It’s recognized in most countries and makes renting a car so much easier.
Documents: When it comes to important documents, don’t just keep them tucked in a folder. Digital & Paper Copies are lifesavers. Store the digital copies in an encrypted cloud folder and share one with a trusted friend. I also save boarding passes and tickets in a secure folder on my phone for quick offline access.

2. Health, Age-Related Needs & Insurance
Insurance: Traveling outside Canada? Your provincial health plan likely covers very little. Before you go, verify your travel medical insurance covered by the province/territory. Get expanded one if necessary. Ensure it includes emergency evacuation and covers pre-existing conditions.
Medications: Pack enough medications in their original pharmacy containers, along with prescriptions in case you need replacements. If you carry syringes or CPAP batteries, a doctor’s note is a good idea.

Vaccinations: Vaccinations matter too; check with a travel clinic six weeks before you leave to see if you need malaria pills or a yellow fever shot.
Fitness/Mobility: And don’t forget fitness & mobility concerns. If you plan to do long walking tours or explore high altitudes, have a chat with your physician to make sure you’re set.
3. Money & Finances
Bank/Credit Cards: Make sure you notify your bank and credit card companies about your travel dates. You don’t want your card blocked because of “suspicious activity.”
Transaction Fees: Also, consider using a card that doesn’t charge the usual 2.5% foreign transaction fee.

Local currency: Carry a small amount of local currency for immediate expenses and some USD bill as a backup. It’s universally accepted in a pinch.
Automated Bill Payments: Set up automated bill payments so nothing is missed while you’re away.
Online Access to Accounts: Lastly, ensure you have online access to your accounts, cloud account where your documents are saved etc.
4. Home, Property & Security – Planning a Long Trip
Now, let’s talk about what you’re leaving behind – your home.
Mail Hold/Redirect: If you’ll be away for a while, consider setting up a mail hold or redirect with Canada Post. Or, ask a neighbor to collect it for you.
Smart Timers: A few smart timers and lights can make your home look lived-in. If you have grocery deliveries, pause them while you’re away to avoid boxes piling up at the door.
Heating/Water: In winter months, be sure to keep your furnace running at a safe minimum and shut off the main water valve or install a leak detector.

Home Insurance Clause: Many insurance policies require someone to inspect the property at regular intervals if it’s vacant. Ask a friend or hire a service to check in, and make sure their visits are logged.
Vehicle Care: If you’re leaving a vehicle behind, top up the fuel, disconnect the battery, or secure it in a safe parking spot if you live in an area prone to floods or heavy snow.
5. Work & Digital Life – Planning a Long Trip
For work, it’s all about planning ahead.
Out of Office: Set up an out-of-office plan: delegate key tasks, update shared calendars, and make sure the team knows who’s in charge of what.
Syncing: Before you jet off, sync your laptop and phone with your cloud account.
Find My Device: Activate Find My Device or similar tracking features for extra security.
Roaming Data: Canadian service providers tend to be expensive when it comes to roaming. Check for cheaper packages from other providers.

eSims: Alternatively, look into eSIM options. eSIMs are amazing – you can keep your main SIM and use a temporary one for travel without physically swapping cards. They come in various options: one-week, one-month, region-specific, or even global plans. Just remember: apps like Maps and Facebook can gobble up 1GB of data in just a few days.
Power Banks & Universal Plug Adapters: Don’t forget your portable power bank and universal plug adapter. These days, our devices are practically our lifelines. Just be mindful that some airlines and countries have restrictions on power bank wattage; check for them.
6. Government Level Precautions
Travel Advisories: Before you fly off, always check the Travel Advice & Advisories on Travel.gc.ca for up-to-date security or health alerts.

Register with Global Affairs: Also, don’t forget to register with the Registration of Canadians Abroad. This allows Global Affairs Canada to reach you in case of a crisis. Here’s the link to get that done: Registration of Canadians Abroad.
Taxes: If your travel plans overlap with the April 30 tax filing deadline, make sure to file early or have someone you trust handle it for you.
7. Emergency Kit & Contacts

Emergency Kit: An emergency kit isn’t just for road trips. Pack a physical list of key phone numbers – your insurer, credit card loss hotline, and the Canadian diplomatic mission in the country you’re traveling to. A small first aid kit, spare glasses, and a USB with medical files and travel documents can be lifesavers in a pinch.
8. Packing Strategy for 30 Days
Packing: Packing for a long trip? Think in terms of at least one week of essentials. Consider that in some countries/restaurants, formal dining might require specific attire – like closed-toe shoes or no shorts. It’s always good to pack accordingly. When you’re settled in, look for local laundry services, if the place you stay doesn’t offer cost-efficient laundry services; they can be a lifesaver.

Layering: Pack multipurpose layers; Canadians often underestimate the impact of heat and humidity abroad or the chill of air-conditioned spaces. Also, throw in a compact rain jacket, sun hat, and comfortable walking shoes.
9. Pets, Parents & Other Dependents
Dependents: If you have pets, parents, or other dependents, make sure you’ve planned for their care. Confirm vet records, medication instructions, and any respite care schedules. When planning a long trip, it’s also smart to provide a notarized letter authorizing emergency treatment decisions if needed.
10. Re-entry to Canada
Customs Allowances: After 30+ days abroad, you’re entitled to an $800 CAD duty-free limit. Be mindful of alcohol and cigarette restrictions. Also, ensure that any food or agricultural items you bring back comply with CFIA regulations (CFIA Food Inspection).
Safe travels!