Your 90-Day Snowbird Checklist: Everything to Do Before Leaving Canada

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You’ve made the decision. You’re spending this winter somewhere warm. Now comes the part that keeps people up at night: actually getting ready to go.

We’ve watched enough Canadians prepare for their first snowbird season to know how it usually plays out. The big decisions — where to go, how long to stay — get settled early. It’s the hundred smaller things that sneak up on you. The prescription that takes two weeks to fill. The home insurance clause you didn’t know about. The bank card that gets frozen on your first day in Mexico because nobody told Visa you were leaving the country.

This is the checklist that prevents all of that. Ninety days of tasks, broken into four phases, in the order they need to happen. Print it. Tape it to your fridge. Check things off as you go. By departure day, you’ll be the most prepared person at the airport.

If you haven’t figured out the big-picture strategy yet — where to go, how long, what it costs — start with our 6-month snowbird planning timeline. That’s the thinking piece. This is the doing piece.

All costs in CAD.

90-60 Days Before Departure: The Foundation

This is where you lock in the decisions that everything else depends on. Rushing this phase is how people end up with expired passports at the airport.

Confirm your destination and rental

If you’ve already chosen your city and have a rental lined up, you’re ahead of the game. If not, this is your last comfortable window to decide. Good long-term rentals in popular snowbird destinations — Lake Chapala, Puerto Vallarta, the Algarve — get snapped up 2-3 months before high season.

Not ready to commit to a full-season rental? Book an Airbnb or short-term rental for your first two weeks. That gives you time to scout neighbourhoods in person before signing a longer lease. It costs a bit more upfront, but it’s cheaper than locking into a place you don’t love for four months.

Check your passport

Your passport needs to be valid for at least six months beyond your planned return date. Not your departure date — your return date. Most countries enforce this, and airlines will deny boarding if you don’t meet it. If your passport expires within the window, renew it now. Processing times in Canada run 4-6 weeks by mail, sometimes longer in peak season.

Start the visa process (if needed)

Many Canadian snowbird destinations let you stay 90-180 days on a tourist entry, no visa required. But if you’re planning a longer stay or want the flexibility to extend, start the paperwork now. The Mexico Temporary Resident Visa requires a consulate appointment and proof of income — not something you want to rush. Portugal’s D7 visa has an even longer lead time. Check the requirements for your specific destination.

Notify your bank

Call your bank and every credit card company you use. Tell them you’ll be abroad, which country, and for how long. This sounds simple, and it is — until you skip it and your card gets locked for “suspicious activity” while you’re trying to pay for a taxi from the airport. Some banks let you set travel notifications online. Others require a phone call. Do it now while you’re thinking about it.

Research health insurance

This is the single most important task on this entire checklist. Your provincial health card covers almost nothing outside Canada. A hospital stay abroad without insurance can cost $20,000-60,000 CAD — one of the biggest financial risks snowbirds face, and one of the easiest to cover.

Start researching travel medical insurance plans now. You’re looking for emergency medical coverage, medical evacuation, 24/7 assistance, and direct hospital billing. Pay close attention to pre-existing condition clauses — most plans require your conditions to be stable for 90-180 days before departure. If your doctor changed a medication recently, that matters.

We break down exactly what to look for in our health insurance guide for Canadians abroad.

Book your flights

Midweek departures (Tuesday, Wednesday) are consistently cheaper than weekend flights. For a November departure to Mexico, booking 60-90 days out usually hits the sweet spot for pricing. Set a fare alert if you’re flexible on dates — a one-day shift can save $100-200 on a return ticket.

Phase 1 checklist:

  • Destination confirmed (or short-term Airbnb booked for scouting)
  • Passport checked — valid 6+ months beyond return date
  • Visa application started (if applicable)
  • Bank and credit card companies notified
  • Health insurance research started — shortlisted 2-3 providers
  • Flights booked (or fare alerts set)

60-30 Days Before Departure: Medical, Money, and Home

The research phase is over. Now you’re buying, booking, and arranging. This is the busiest stretch — most of the real logistics happen here.

Buy travel medical insurance

Don’t put this off any longer. Purchase your policy at least 30 days before departure so you have time to review the documents, understand the claims process, and save the emergency number in your phone. SafetyWing offers flexible month-to-month plans that work well for snowbirds who aren’t sure of their exact return date. Traditional providers like Manulife and Blue Cross offer fixed-term plans with strong pre-existing condition coverage for retirees.

Whatever you choose, read the pre-existing condition stability clause carefully. This is where most denied claims happen.

Get your prescriptions in order

Ask your doctor for a 3-6 month supply of every medication you take. Some pharmacies won’t fill more than 90 days at once, so you may need your doctor to write a specific note or call the pharmacy directly. Bring the medication in original pharmacy bottles with labels — customs officials in every country respond better to clearly labelled prescriptions than loose pills in a Ziploc.

Book a full physical

Schedule a physical with your GP. Ask for a medical summary letter that lists your conditions, medications, allergies, and blood type. This is for you, not for customs — if you end up in a foreign hospital, a one-page medical summary in English saves time and potentially saves your life. Family doctors are booked weeks out, so call early.

Handle CRA and government notifications

If you’re staying abroad for six months or longer, update your mailing address with CRA. This ensures you receive tax slips and correspondence on time. If you’re gone for a standard snowbird season (under six months), you typically remain a Canadian tax resident and don’t need to file a departure return — but confirm this with your accountant if your situation is complex.

Set up a Wise account

If you haven’t already, open a Wise account. It lets you convert CAD to pesos, euros, or baht at the real mid-market exchange rate — no markups, no mystery fees. Canadian banks charge $25-45 per international wire transfer and add 2-4% on the exchange rate. Over a five-month season, Wise saves most snowbirds $300-800 CAD. Set it up now, verify your identity, and do a small test transfer so you know it works before you need it.

Handle the mail

Set up Canada Post mail forwarding to a trusted family member or friend, or request a mail hold. Bills, government correspondence, and insurance documents don’t stop arriving because you’re in Mérida. A missed notice from CRA or your insurance provider can create problems that take months to untangle from abroad.

Arrange for your Canadian home

If you own your home:

  • Home insurance: Call your provider and tell them the house will be unoccupied. Many policies have vacancy clauses that void coverage after 30-60 days. You may need a rider or adjusted policy. This call could save you tens of thousands on a denied claim from a burst pipe.
  • House sitter or regular checks: Insurance often requires someone to check the property weekly. A family member, trusted neighbour, or paid house sitter.
  • Winter prep: Set the thermostat to at least 15°C, shut off the water supply to outdoor taps, and arrange for snow removal. Put lights on timers.
  • Car storage: If you’re leaving a vehicle, arrange covered storage or ask someone to start it and move it periodically. Check your auto insurance — you may be able to reduce coverage to comprehensive-only while it’s parked.

Phase 2 checklist:

  • Travel medical insurance purchased and policy documents saved
  • Prescriptions filled (3-6 month supply)
  • Physical booked (or completed) — medical summary letter in hand
  • CRA address updated (if staying 6+ months)
  • Wise account set up, verified, and test transfer completed
  • Mail forwarding or hold arranged
  • Home insurance updated for vacancy
  • House sitter or weekly check-in person confirmed
  • Car storage arranged

30-7 Days Before Departure: Final Setup

The big tasks are done. This phase is about tying up loose ends and making sure nothing falls through the cracks in the last stretch.

Final banking setup

Confirm that every credit card you’re bringing has been flagged for international use. Set up online and mobile banking on all accounts — you’ll be managing everything from your phone. Make sure you know how to do an e-transfer, check your balance, and pay bills remotely. If your bank has a daily ATM withdrawal limit, consider requesting a temporary increase for your first week abroad.

Download your essential apps

Get these on your phone before you leave Canada:

  • Wise — for money transfers and exchange rate checks
  • WhatsApp — the default messaging app in Mexico, Portugal, and Thailand. Your landlord, local contacts, and service providers will all use it
  • Google Translate — download the offline language pack for your destination’s language
  • Google Maps — download offline maps for your destination city and surrounding area
  • Uber or Didi — Uber works in Portugal and Thailand; Didi is the go-to in Mexico. Both are safer and cheaper than negotiating taxi fares in a new city
  • Your airline’s app — for boarding passes and flight updates

Print document copies

Phones break. Phones get stolen. Phones run out of battery at customs. Print paper copies of:

  • Travel medical insurance policy and emergency phone number
  • Visa or entry permit (if applicable)
  • Medical summary letter and prescription list
  • Emergency contacts — both in Canada and at your destination
  • Rental confirmation with landlord’s phone number and address
  • First two pages of your passport (as a backup)

Keep these in a separate bag from your passport. If one goes missing, you still have the other.

Pack

You’re living somewhere warm for months, not packing for every possible scenario. Pack light, pack practical, and leave room in your suitcase for things you’ll pick up locally. Our packing list for Canadians moving abroad covers this in detail — including the things most people forget and the things most people overpack.

Confirm rental details

Message your landlord or property manager. Confirm: the exact move-in date, key handoff process (where and when), what’s included in the rental, and whether there’s anything you need to bring. Ask for the nearest grocery store, pharmacy, and ATM. This five-minute conversation prevents a confusing first day.

Set up a VPN

Install a VPN on your phone, laptop, and tablet. You’ll need it for Canadian banking sites that block foreign IP addresses, streaming services with regional restrictions, and any time you’re using public Wi-Fi. Set it up and test it at home while you still have your Canadian internet connection.

Phase 3 checklist:

  • All credit cards flagged for international use
  • Online and mobile banking confirmed working
  • Essential apps downloaded (Wise, WhatsApp, Google Translate, Maps offline, Uber/Didi)
  • Paper copies of all key documents printed and packed separately
  • Packing done
  • Rental details confirmed with landlord
  • VPN installed and tested on all devices

The Week of Departure: You’re Ready

Almost everything is done. This week is about the small things — and about taking a breath.

Check in online

Most airlines open online check-in 24 hours before departure. Do it. Choose your seat, download your boarding pass, and avoid the check-in line at the airport. If you have checked bags, you’ll still need to drop them at the counter, but you’ll skip the queue.

Confirm your airport transport

Whether it’s a family member driving you, a pre-booked shuttle, or a parking spot at the airport — confirm it. Nothing adds stress to departure day like scrambling for a ride at 5 a.m.

Do a final walkthrough of your Canadian home

Walk through every room. Check:

  • Thermostat set to 15°C or higher
  • Water shutoff valves closed for outdoor taps and any fixtures prone to freezing
  • All windows and doors locked
  • Lights on timers
  • Fridge cleaned out (or stocked minimally for your house sitter)
  • Garbage and recycling taken out
  • Spare key left with your house sitter or emergency contact

Breathe

You’ve spent three months getting ready. Your insurance is in place. Your prescriptions are packed. Your home is winterized. Your rental is confirmed. Your bank knows where you’re going.

You are more prepared than 90% of the people making this trip. The checklist is done. Now enjoy the part you’ve been planning for.

The Quick Reference: Full Checklist at a Glance

For the fridge door:

90-60 days: Destination + rental. Passport validity. Visa (if needed). Bank notification. Insurance research. Flights.

60-30 days: Buy insurance. Prescriptions (3-6 months). Physical + medical letter. CRA notification (if 6+ months). Wise account. Mail forwarding. Home insurance. House sitter. Car storage.

30-7 days: Final banking. Apps downloaded. Documents printed. Packing. Rental confirmed. VPN set up.

Week of: Online check-in. Airport transport. Home walkthrough. Go.

What to Read Next

This checklist gets you out the door. These guides help with the decisions behind it:

Your Next Step

Download the free Budget Worksheet for Retirees — plug in your CPP, OAS, and pension income and see exactly what a snowbird season costs against your real numbers.

Want the complete package? The Mexico Relocation Kit ($59 CAD) covers visas, banking, healthcare, neighbourhoods, and a 30-day action plan — everything behind the checklist items, in one place.

This post contains affiliate links to SafetyWing and Wise. We may earn a commission if you sign up through our links, at no extra cost to you. We only recommend services we’d use ourselves.

This guide is for informational purposes only. Visa requirements, insurance terms, tax rules, and healthcare policies change — always confirm details with official sources and qualified professionals before making decisions. All costs in CAD unless noted.

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