Types of travel insurance · Travel at My Pace

After my stroke in 2016, planning a trip means planning for heat, stairs and rest stops. It also means asking a less fun question: what happens if one of us needs a doctor on the road, or if we have to cancel a trip we've already paid for?

Joanna and I did carry travel insurance on our trip to Japan that ran from December 2019 into 2020. We found our plan through Squaremouth, a site that compares plans from different insurers side by side.

Between Christmas and New Year's, Joanna got sick with what we believe was COVID. It was before testing was widespread. We didn't have to go to the hospital, but knowing we were covered made a stressful event a little less stressful.

This guide covers the main types of travel insurance, when each one tends to make sense, Cancel For Any Reason (CFAR), and pre-existing condition waivers. It's general information, not advice about your own trip or any specific policy. Read the policy itself before you buy.

Disclosure: the Squaremouth link on this page is an affiliate link. If you buy a policy through it, I may earn a commission at no extra cost to you. I'm not a licensed insurance agent, and I can't tell you which policy is right for you.

Start with three questions

Before you compare plans, it helps to know what you're actually trying to cover:

What prepaid costs are non-refundable? Flights, cruises, tours and lodging deposits add up fast if you have to cancel.
What medical and evacuation coverage already applies at the destination? Your health plan at home may not travel with you. Medicare usually doesn't cover health care outside the U.S.
Is there a special risk? Frequent travel, a remote itinerary, or rental-car damage can change what you look for.

Not every traveler needs a policy. A fully refundable, low-risk trip close to home may need little extra coverage. A trip with a large non-refundable deposit, or one that takes you far from your usual doctors, is a different story.

Four kinds of coverage

Most plans you'll compare fall into one of these groups.

Comprehensive (medical plus cancellation)

This is the bundled plan. It typically pairs trip cancellation and interruption with benefits that may include emergency medical care, evacuation, delays and baggage. If you have meaningful non-refundable deposits — a cruise, a tour, flights or lodging — this is usually the type worth comparing. It's also the type that can offer a Cancel For Any Reason add-on, though not every comprehensive plan does.

Travel medical insurance

This type focuses on unexpected medical treatment during the trip, and often emergency evacuation. It generally does not insure the full cost of cancelling the trip the way a comprehensive plan can. It can be a better fit for an international trip with little prepaid money at risk, or for a longer stay with flexible lodging, after you've checked what your existing health insurance would actually pay abroad. Students and extended-stay travelers may need a specialized version that lasts the whole stay.

Medical evacuation membership

This is a separate transport service or membership. It may arrange eligible medical transport under its own rules, but it does not replace coverage for hospital or physician bills. If you're worried about reaching advanced care, or about getting to a preferred hospital, this can be worth looking at as an addition, not as a substitute for medical insurance.

Annual or multi-trip plans

An annual plan can cover multiple eligible trips during a policy year. Trip-length, medical and cancellation caps differ a lot from plan to plan, and cancellation coverage is often limited. Squaremouth notes that Cancel For Any Reason is not offered with annual plans. If you travel often, an annual plan can be convenient, but compare it against single-trip policies, and look hard at the limits on your most expensive trip. That one trip may still need its own comprehensive policy.

Cancel For Any Reason

Cancel For Any Reason, or CFAR, is an optional benefit on some eligible plans, not a type of insurance by itself.

Standard trip cancellation only pays for reasons listed in the policy, such as a covered illness or severe weather. CFAR may reimburse a portion of your insured, non-refundable costs if you cancel for a reason the standard benefit does not cover. The reimbursement is typically partial: Squaremouth's CFAR guide says plans generally pay 50 to 75 percent of those costs, not the full amount.

The rules are stricter than they sound:

You usually have to buy an eligible policy within 14 to 21 days of your first trip deposit.
You typically have to insure the full prepaid, non-refundable cost of the trip.
You usually have to cancel the whole trip, often at least two or three days before departure, not the day you were meant to leave.
Eligibility, notice rules and reimbursement percentages vary by plan and by where you live. Squaremouth's guide says CFAR is generally unavailable for New York and Washington residents, with only limited workarounds in those states.

If your bookings are mostly refundable, or the trip itself is inexpensive, CFAR may not add much. If a large non-refundable payment is on the line and you want more flexibility than the standard covered reasons, it's worth comparing, as long as you can meet the deadlines.

Pre-existing condition waivers

Most travel insurance excludes pre-existing conditions by default. Some comprehensive plans will waive that exclusion if you meet the plan's rules. Those often include buying within a set number of days of your first trip deposit (commonly 14 to 21), insuring the required trip costs, and meeting the plan's medical eligibility rules, such as being medically able to travel when you buy.

What counts as pre-existing depends on the policy. Insurers typically look back at your medical history for a set window before you bought the policy, often 60 to 180 days. A condition that was stable on the same medication may not count, but a change in medication or dose during that window can change the answer.

When we bought our plan, we weren't asked about my stroke. Don't take that as a promise that you'll be covered. Not being asked isn't the same as being covered, and this is where policies differ most. Read each plan's look-back period, whether it offers a waiver, and whether that waiver has a deadline. If you're not sure, ask the insurer before you buy.

If Japan is the trip, or a health condition is already part of your planning, I wrote a longer guide on Japan at My Pace: Travel insurance for Japan when your health is part of the plan.

When each type tends to make sense

These are starting points, not a recommendation for your trip:

A cruise, tour, or flights and hotels with strict cancellation penalties. Compare a comprehensive plan that covers both the money you've already spent and medical care on the trip.
A month abroad with flexible, refundable lodging. After you check what your health insurance covers overseas, travel medical coverage may be the more important question.
Several trips this year, including one expensive vacation. Compare an annual plan against buying trip by trip, and look at the trip-length and cancellation limits on the costly one.
A remote hike or a place far from a major hospital. Review emergency medical and evacuation benefits. A transport membership might fill a specific gap, but it doesn't replace medical coverage.
A refundable weekend close to home, traveling by car. Cancellation insurance may add little if you can recover the full trip cost and your existing coverage already addresses the other risks.
A semester studying abroad. Look for a travel medical plan that lasts the whole stay, fits the location, and meets any school requirements.
A relative visiting the United States. Consider visitor medical coverage, after checking what their current plan would actually pay here. Medical care in the U.S. can be expensive.

When to compare, and where I looked

The best time to compare coverage is when you book, or when you make the first trip deposit. Some optional benefits and waivers have deadlines that start on that day.

We found our plan through Squaremouth. It lets you compare plans from different insurers side by side, including filters for things like a pre-existing condition waiver. Whatever you choose, compare the policy wording, not just the price. I'm not a licensed insurance agent, and I can't tell you which policy is right for you.

Sources

Official and Squaremouth pages read November 10, 2026.

Opening hours, routes and rules change; check the official pages before you go. Planning links for every guide are on the Plan page.