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A Vancouver Island Snowbird Resource

Snowbird Pre-Departure Checklist

What to review before leaving Vancouver Island and heading to the United States for the winter.

12 StepsOne practical departure plan
HomeInsurance and property checks
HealthCoverage and medications
BorderDocuments and U.S. day counts

Prepare Before You Travel

Have a Plan Before You Land

Heading south for the winter should be enjoyable, not stressful. Before leaving Vancouver Island, take time to organize the details that protect your home, health, finances and family communications while you are away.

This checklist was contributed by Gerry Scott of Snowbirds Cross-Border Wealth Management and edited for clarity and online use. Open each section below and work through the items that apply to your trip.

The Complete Checklist

What to Review Before Heading South

Requirements vary by policy and personal circumstances. Treat this as an organizing guide, then confirm the details with the appropriate insurer or professional.

01Protect Your Vancouver Island Home
  • Arrange for a trusted neighbour, friend, family member or property manager to check your home regularly.
  • Ask your home insurer exactly how often inspections are required. Do not assume a weekly visit is sufficient.
  • Give your home checker a key, alarm instructions, your contact information and appropriate emergency contacts.
  • Consider keeping a written or electronic record of every visit.
  • Confirm how your policy addresses the main water supply, leaks, heating and an unoccupied home.
  • Check the heating system, smoke alarms and carbon-monoxide detectors before leaving.
  • Secure outdoor furniture and barbecues against Vancouver Island winter storms.
  • Arrange for mail, packages, garbage and recycling, and confirm that alarms, cameras and smart-home devices can be monitored remotely.

Important: Vacancy and unoccupied-home conditions differ between policies. Get the requirements directly from your insurer and follow them precisely.

02Understand Your Travel Medical Insurance
  • Review coverage limits, deductibles, exclusions and requirements involving pre-existing medical conditions.
  • Understand the stability period and whether a recent change in medication, treatment or medical condition may affect coverage.
  • Confirm the maximum number of days covered for each trip.
  • Save the insurer's 24-hour emergency assistance number in both travellers' phones.
  • Carry policy information in your wallet and keep a digital copy on your phone.
  • Make sure a family member at home knows where the information is stored.
  • Know the policy procedure for contacting the insurer during a medical emergency.

Do this before departure: An insurance card in a drawer is not enough. Know whom to call and what the policy requires before you need help.

03Organize Prescriptions and Medications
  • Speak with your doctor and pharmacist well before departure about an extended supply where permitted.
  • Keep medications in their original labelled containers.
  • Carry a current list of medications and dosages.
  • Keep essential medication with you while travelling rather than in checked luggage.
  • Know how a lost or damaged prescription could be replaced while you are in the United States.
04Know Your U.S. Day Count
  • Record every day spent in the United States. Do not rely only on memory or airline itineraries.
  • Recognize that U.S. immigration limits and U.S. tax-residency calculations are separate rules.
  • Learn how the IRS Substantial Presence Test uses days across three calendar years.
  • Ask an appropriate cross-border tax professional whether IRS Form 8840 may apply to you.
  • Review your U.S. entry and exit records periodically for accuracy.
  • Consider using the Snowbirds U.S. Day Tracker to maintain your records.
05Review Passport, Border and Immigration Details
  • Check your passport expiry date well before departure.
  • Confirm how long you are permitted to remain in the United States based on your circumstances.
  • Do not assume that owning U.S. property gives you additional immigration rights.
  • Keep records supporting your ties to Canada where appropriate.
  • Know your expected return date and be prepared to explain the purpose and duration of your visit.
  • Get professional advice before arriving at the border if your immigration circumstances are unusual.
06Stay Connected With Family
  • Set a regular check-in routine before leaving.
  • Make sure family members have your U.S. address, phone number and itinerary.
  • Give a trusted person your emergency contacts, insurance information and important medical details where appropriate.
  • Let family know when you are travelling between destinations.
07Prepare Your Banking and Finances
  • Notify your financial institution about your travel plans if required.
  • Confirm that your credit and debit cards will work in the United States and carry more than one payment method.
  • Review foreign-exchange and transaction fees.
  • Confirm secure access to your Canadian accounts and review automatic bill payments.
  • Have a plan for major unexpected costs, particularly a medical emergency.
  • Make sure trusted-contact information, powers of attorney and estate documents are current and accessible where appropriate.
08Prepare Your Vehicle and Driving Plan
  • Have the vehicle serviced and check tires, brakes, fluids, battery and emergency equipment.
  • Confirm that your Canadian auto insurance provides appropriate U.S. coverage.
  • Keep registration and insurance documents accessible.
  • Make sure roadside assistance applies in the United States.
  • Plan safe overnight stops instead of trying to cover too much distance in one day.
09Ready Your U.S. Property or Accommodation
  • Confirm that utilities, internet and other services will be ready when you arrive.
  • Review U.S. property and liability insurance.
  • Confirm that smoke and carbon-monoxide detectors are working.
  • Keep local emergency and property-management contacts available.
  • If you own U.S. real estate, obtain advice about any cross-border tax and estate-planning considerations that apply to you.
10Build an Emergency Information Package

Create both a physical and digital folder containing:

  • Passport copies and Canadian and U.S. addresses
  • Travel medical insurance policy and emergency assistance number
  • Medication list, prescription details and doctors' contact information
  • Emergency family contacts
  • Vehicle insurance and roadside-assistance details
  • Financial advisor, accountant, power of attorney and estate-planning contacts
  • Home-insurance information and the contact for the person checking your Vancouver Island home

Make sure both spouses or partners know where the complete package is stored.

11Educate Yourself Before You Leave

Review the questions that may affect healthcare, insurance, taxation, immigration and U.S. day counting before arriving at your winter destination. Gerry has selected short videos and podcast episodes to help snowbirds recognize the issues that may require further advice.

12Have a Plan Before You Land

Gerry's book, Snowbirds Heading South for the Winter: What You Don't Know Will Hurt You, is a practical guide to U.S. day counting, immigration, taxation, healthcare, travel insurance and other cross-border considerations.

The point is not to make travelling south feel more complicated. It is to understand the rules, organize your documents, protect your home, confirm your healthcare coverage, track your days and stay connected with the people who matter.

View Gerry's Book

Continue Your Planning

Helpful Cross-Border Resources

These resources support the checklist and help identify questions to raise with the appropriate professionals.

Snowbirds Expat Radio Podcast

Hear Gerry's conversations with professionals who work with the financial, tax, immigration, healthcare and lifestyle realities of living across the Canada-U.S. border.

Explore the Podcast

Snowbirds U.S. Day Tracker

Keep a practical record of the days you spend in the United States and avoid relying on memory when reviewing immigration or tax-residency questions.

Explore the Day Tracker

Cross-Border Resource Hub

Explore Denise's resources for returning Canadians, snowbirds coming home permanently and U.S. residents considering a move to Vancouver Island.

Visit the Resource Hub

Making Vancouver Island Home Year-Round

If maintaining two homes no longer fits the life you want, review the real estate questions involved in making Vancouver Island your primary home.

Plan Your Homecoming

About the Contributor

Gerry Scott, CFP®, CIM®, CRPC®

Gerry Scott is a Portfolio Manager and the Founder of Snowbirds Cross-Border Wealth Management. He has more than 32 years of experience helping Canadians and Americans navigate the financial, tax, immigration, retirement and lifestyle considerations of living on both sides of the border.

He hosts the Snowbirds Expat Radio Podcast, is the author of two cross-border books and created the Snowbirds U.S. Day Tracker and Canada Physical Presence Tracker.

Thinking Beyond This Winter?

Is It Time to Make Vancouver Island Home Year-Round?

If the upkeep, travel and cost of maintaining two homes are beginning to outweigh the benefits, Denise can help you assess the Vancouver Island real estate side of simplifying.

Important information: This checklist is general educational information only. Insurance policies, immigration status, tax circumstances, healthcare coverage and financial needs vary by individual. Confirm requirements with your insurance providers and obtain advice from appropriately qualified professionals who can review your circumstances. Denise Hodgins provides real estate services and does not provide tax, legal, immigration, insurance or financial advice.

Gerry Scott is a Portfolio Manager with Raymond James Ltd. Raymond James Ltd. is regulated by the Canadian Investment Regulatory Organization and is a member of the Canadian Investor Protection Fund. Raymond James (USA) Ltd., member FINRA/SIPC.