A Snowbird Couple Plans a 5-Month Florida Winter

This is an illustrative scenario based on situations we commonly see. The names and details are fictional and are not based on any actual client. We’ve built it to show how a snowbird couple with a few medical conditions works through the questionnaire, the options and the price for a long US winter.

The short version: Diane (68) and Robert (71) from Orléans wanted five months in Fort Myers. Robert takes medication for type 2 diabetes and blood pressure. Because those conditions had to be stable for a set period before departure, the insurer’s stability rules decided which policy they could use. A single-trip policy for 151 days with a $1,000 deductible came to an indicative $2,900–$5,200 for both of them.

If you’re retired, heading south for the winter and taking a prescription or two, this is for you.

The couple and the trip

Diane and Robert retired three years ago and sold their cottage to fund winters somewhere warm. This year they’ve rented a condo in Fort Myers from November 1 to March 31, which is 151 days door to door.

Their health, as they described it to us:

• Robert (71): type 2 diabetes managed with one oral medication, and high blood pressure on one medication. No changes to either prescription in over three years, no hospital visits, regular check-ups with his family doctor.
• Diane (68): a knee replacement 14 months ago, fully recovered. No prescriptions.
• Both non-smokers.

Neither has retiree benefits from a former employer. Robert has a premium credit card that “includes travel insurance,” which he assumed would cover them. They came to us in early October after a neighbour’s story about a US hospital bill made them nervous.

The risk: what OHIP does and doesn’t do outside Canada

OHIP is an Ontario plan. It covers medically necessary physician and hospital care inside the province and pays little or nothing toward emergency treatment outside Canada. In the United States, an ambulance, an overnight stay and a few tests can run into tens of thousands of dollars; a cardiac event or surgery can be far more. Our article on whether OHIP covers travel explains the details.

There were two other rules Diane and Robert needed to know:

The OHIP residency rule. Ontario generally allows you to be outside the province for up to 212 days in any 12-month period and keep your OHIP coverage. At 151 days, they were well inside the limit, but a spring trip to Europe would eat into the remainder, so they started keeping a day count.

US entry and tax rules. Canadian visitors are generally admitted to the US for up to six months at a time, and spending a large number of days there over several years can have US tax implications. We told them to confirm the details with a cross-border accountant, which is outside what we do.

The medical piece was the part we could fix.

The medical questionnaire came first

For travellers over 60, most snowbird policies price and underwrite from a medical questionnaire. The single most important concept in that questionnaire is the stability period: a condition must have had no new symptoms, no new tests or treatment, no hospital visits and no change in medication or dosage for a set number of days before departure. Claims related to a condition that isn’t stable are generally excluded.

Two things caught our attention:

1. Stability periods differ by insurer and by age. Some insurers require 180 days of stability for applicants over a certain age, others offer 90 days, sometimes for a higher premium. For Robert’s age band, the insurers we compared split roughly down the middle.
2. Robert’s July dosage change. When we went through his file line by line, he mentioned that his doctor had increased his blood pressure medication in mid-July. A dosage change counts as a change in treatment under most policies. By November 1, that was about 108 days, so his blood pressure condition would satisfy a 90-day stability requirement but not a 180-day one.

That single detail eliminated roughly half the market for him. It’s exactly the kind of thing people forget, and it’s why we walk through the questionnaire together rather than sending a link. Our guide to travel insurance with pre-existing conditions covers how these questionnaires work.

Diane’s knee replacement was a non-issue: it was complete, the follow-up was done, and she was on no medication.

The options compared

We laid out five ways to cover the winter.

Option	Covers 151 days?	Robert’s conditions	Verdict
Credit card travel medical	Typically the first 15–31 days of a trip only; many cards reduce or end coverage at 65	Usually subject to stability rules with limited detail	Not an option for this trip
Annual multi-trip plan plus a top-up	Annual plan covers trips up to a set length (often 30 or 60 days); a top-up from the same insurer extends it	Same questionnaire; the top-up must be with the same insurer to avoid a coverage gap	Workable, but only cheaper if they take several other trips
Single-trip policy, $0 deductible	Yes, 151 days	Needs an insurer with a 90-day stability period for his age	Simplest, highest premium
Single-trip policy, $1,000 deductible	Yes, 151 days	Same	Simplest, lower premium
Self-insure	Yes	N/A	Not realistic against US hospital costs

The credit card was the first surprise. Robert’s card did include emergency medical, but for a limited number of days per trip and with different terms after 65. Our article on credit card travel insurance explains why that’s typical.

The annual plan was a real contender, since they also visit their daughter in Vancouver twice a year. In the end, the single-trip policy was cheaper for this year, and travel within Canada is a smaller risk because OHIP still covers physician and hospital care in other provinces. The annual vs. single-trip comparison goes deeper on that math.

The recommendation and indicative cost

We recommended a single-trip travel insurance policy for November 1 to March 31 with a $1,000 deductible, placed with an insurer offering a 90-day stability period at Robert’s age. Diane went with the same insurer for simplicity, although she’d have qualified anywhere.

All figures are indicative premiums for this illustrative scenario. Actual rates depend on age, the medical questionnaire, trip length, deductible and insurer, and these are not quotes.

Traveller	Coverage	$0 deductible	$1,000 deductible
Diane (68), no conditions	151 days emergency medical, $5M limit	~$1,200–$2,100	~$1,000–$1,800
Robert (71), stable diabetes and blood pressure	151 days emergency medical, $5M limit	~$2,300–$3,900	~$1,900–$3,400
Combined		~$3,500–$6,000	~$2,900–$5,200

The $1,000 deductible saved them several hundred dollars combined. They could comfortably absorb a $1,000 bill for a rare claim, so it was an easy call.

We also added trip interruption coverage, since the condo rent was prepaid and non-refundable. They passed on trip cancellation because the flight was booked on points. For a broader look at pricing, see how much travel insurance costs in Canada.

What happened

They left on November 1 as planned. Before leaving, we gave them two instructions: keep the insurer’s 24-hour assistance number in both phones and on the fridge, and call us if any doctor changed any medication before departure. Nothing changed, so the policy was issued exactly as quoted.

In February, Diane slipped on a wet pool deck and hurt her wrist. She called the assistance line first, as most policies require, and was directed to a nearby urgent care clinic. The X-ray showed a sprain, not a fracture. The insurer arranged direct billing with the clinic; Diane paid the $1,000 deductible and nothing else. The bill for the visit, imaging and a brace was several times that amount.

Robert had no claims. His blood pressure medication stayed the same all winter, and because it had been stable for the required 90 days at departure, any related claim would have been covered.

They’re back in Orléans now, at 151 days of absence, planning the Vancouver trips around the 212-day limit. Next year we’ll re-run the questionnaire from scratch, because stability is measured from the new departure date and a year is a long time at 71.

Lessons you can apply

Fill out the questionnaire with your prescription list in hand. Robert’s July dosage change wasn’t something he thought of as “a change in health.” Under most policies it is. Any adjustment to a medication, even a lower dose, can restart the stability clock.

The stability period is a shopping criterion, not fine print. Insurers use different periods, and some vary them by age. If one of you has a condition that changed recently, the insurer with the shorter period may be the only one that fully covers you, even if it isn’t the cheapest.

Don’t rely on a credit card for a long trip. Card coverage is usually built for short vacations. For a winter away, it isn’t enough.

Choose a deductible you can live with. It’s one of the few levers that lower the price without lowering the coverage.

Call the assistance line before treatment when you can. It’s the single most common claims problem we see: someone goes straight to a hospital, doesn’t call, and finds the insurer disputes part of the bill.

Count your days. Both OHIP and the US have limits. A calendar on the fridge is enough.

For more on the general rules for long-stay winters, read our guide to travel insurance for Ontario snowbirds and travel insurance for the USA.

How Hayes can help

If Diane and Robert sound like you, the process takes about half an hour: we go through the medical questionnaire together, compare the snowbird policies available to your age and health across the insurers we work with, and show you the price at two or three deductible levels. Hayes Family Insurance has helped Ottawa snowbirds since 1996, and our advice costs you nothing because the insurers pay us.

Compare travel insurance quotes from Canadian insurers in a couple of minutes, free and with no obligation. Or contact us and we’ll run through your questionnaire before you book.