You don’t have to be a hypochondriac to worry about getting sick during foreign travel. Though it’s possible to receive e-mails, phone calls and text messages almost anywhere in the world, one thing that won’t follow you overseas is your U.S. health insurance. Except in an emergency, most plans (including Medicare) do not pay for medical care abroad. So I generally buy insurance that will cover such expenses and evacuation, if necessary.

Most recently I’ve focused on coverage designed for those who take multiple trips each year, or divide their time between the U.S. and a foreign country. They include the so-called “new nomads,” who work remotely, are raising children outside of the U.S. or enjoy slow travel during the years leading up to and including retirement. Now that we are empty nesters, my husband, Ken, and I, too, lead a more nomadic life, using rental income from our Brooklyn, New York home to finance our adventures.

This year, as we mapped out our itinerary, the question was whether we would be better off with an annual multi-trip plan or a single-trip policy. We are scheduled to spend 83 days in France this fall, return to New York for the holidays, and then escape to Southeast Asia during the dead of winter.

Depending on how many trips a year you take, and the length of those journeys, annual policies can be a cost-effective option. Their most important feature is emergency medical care and evacuation. Trip cancellation coverage, which compensates you for nonrefundable out-of-pocket costs if you call off the voyage for reasons specified in the policy, is not usually included.

This helps make annual policies more affordable: The cancellation component adds substantially to the price of travel insurance. Therefore, it’s a good idea to consider whether you really need that kind of coverage. We don’t, since for the most part we purchase airline tickets using frequent-flyer miles, and book long-term rentals with liberal cancellation policies.

My latest quest, just for medical and evacuation coverage, began on Squaremouth.com, a consumer-friendly website that I have used to buy travel insurance in the past. Prices are the same as if you bought directly from an insurer. (Squaremouth gets a commission from them but doesn’t impose an up-charge.) This site makes it easy to compare policies of 21 different travel insurers, though it doesn’t include all of their offerings. For each provider, there are customer reviews – something that I take with a grain of salt. But I do like the fact that, in the event of a complaint, Squaremouth will mediate with the insurance provider on your behalf.

Another handy feature is that, once you have bought a policy through Squaremouth.com, it generates an emergency information card that you can add to the Apple Wallet on your iPhone.

Like all online platforms, the performance of this one depends on the search criteria that you enter. And this time, when I looked for an annual plan like one we bought last year through Squaremouth.com, the site came up empty. With further probing, I understood why: The company that previously insured us had shortened the maximum trip length. And another major player in this market is not currently offering insurance to New York residents. As happens every time I revisit the subject of travel insurance, the landscape had changed.

I dug deeper, surfing the websites of six insurers, reading the fine print in their policies and talking to a couple of sales representatives. Ultimately I unearthed suitable coverage at a reasonable price. Here are strategies to follow, and the best of what I found on this year’s hunt.

Cover preexisting conditions. Travel insurance generally excludes coverage for preexisting conditions – an illness or medical issue that you had before buying the policy. With single-trip coverage, most insurers will waive the exclusion if you buy the insurance soon after you make the first payment for the trip (whether it’s a deposit or an installment on what you owe). This avoids arguments down the line about whether medical treatment is due to a preexisting condition and therefore not covered by your insurance.

If you don’t buy the policy within the specified time, or are dealing with a multi-trip plan, you will need to pay careful attention to how a particular policy defines “preexisting condition.” This varies enormously. For example, the Atlas MultiTrip plan does not cover most conditions that existed within two years of the policy’s effective date, while GeoBlue’s Trekker Essential plan – another multi-trip policy – looks back to only six months before your purchase date. For the Wander Frequent Traveler plan from Seven Corners, the look-back period is three years, but there’s an important exception: No matter what, the policy covers $20,000 worth of expenses outside the U.S. ($2,500 for those 65 or older).

Multi-Trip Health Insurance Policies Compared

In contrast, under the ExtraCare policy from Berkshire Hathaway Travel Protection – a single-trip plan – you can avoid these limitations if you haven’t been treated (or should have been) within 180 days of the day you buy the policy. You can even be taking medication for the condition, so long as it was controlled without any change in your prescription during that time frame.

Keep an eye on trip-length limits. Annual policies allow you to take as many trips per year as you want, but most now limit the maximum trip length to 30 or 45 days. (Premiums depend on your age and which trip length you choose.) The Trekker Essential and Trekker Choice policies from GeoBlue are far more generous, allowing you to stay away for up to 70 days.

This was 13 days short of what we needed for our French sojourn. Looking for a workaround, I inquired by e-mail as to whether I could get a rider to extend the length of the coverage for this particular trip.

That prompted a phone call from a sales representative. She explained that it’s possible to purchase up to 20 days of extra coverage as a single-trip policy. In our case the extra coverage, with GeoBlue’s Voyager Choice plan, would cost $154.31. When added to the premium of $200 for the annual policy (which would cover our other travels during the coming year without the need for an extension), our total insurance cost would be $354.31. In contrast, buying Voyager Choice just for the France trip would have run us $703.92.

Maintain a home base. Even if you are living home-free, you need a state of residence to buy insurance, says Megan Moncrief, director of sales and marketing at Squaremouth.com. Since states regulate insurance, where you live will determine which policies you are eligible to buy. Still, the fact that a particular policy isn’t available in your state – as was my experience when I shopped for travel insurance this year – may simply mean that state regulators haven’t yet approved changes in a particular policy, Moncrief says.

With travel insurance, your state of residence is significant for another reason, she adds: “If we can’t see where your home is, we can’t see that you’re traveling.” This could be an issue when you submit a claim, since coverage generally ends when you get home. For this purpose, a post office box is enough to show residency, says Moncrief. Just be sure that important mail, such as bills and bank statements, reflect that address, even if you conduct your financial life online.

Buy domestic health insurance. Travel insurance is not typically meant to be your primary source of coverage. Some applications for multi-trip policies, like those of Atlas and GeoBlue, specifically ask whether you have medical insurance in your home country. So even if you are overseas a lot, plan to carry a policy that will cover you in your home state.

Don’t buy more than you need. If you travel often and touch home base between jaunts, a multi-trip policy like GeoBlue’s Trekker Essential can be a great deal. It would cost a 30-year-old only $100 in premiums (an additional $65 to cover a traveling companion that age on the same policy). Likewise, such a plan might be cost-effective for older folks who take multiple trips a year. No matter your age, compare the two types of offerings in light of your upcoming travel plans.

Much as I would have appreciated the convenience of one policy to cover 12 months’ worth of travel, this year a multi-trip plan didn’t make sense for us. Instead, at Moncrief’s suggestion, we purchased Berkshire Hathaway’s ExactCare plan though Squaremouth.com to cover our France trip, and decided to separately insure our winter journey.

At $56 per trip for the two of us, this policy was a better value than others we considered. As is typical, the premium is based partly on age. But unlike other insurers, Berkshire Hathaway cuts the per diem price structure at 30 days, so the cost remains the same if (as in our case) you are away longer than that. The maximum trip length is 180 days. The policy covers $25,000 of medical expenses and $500,000 of evacuation per person. For an extra $12, we could have upgraded to $50,000 per person in medical coverage. That seemed unnecessary since we will be in Europe, where healthcare costs are much lower than they are back home.

If we wanted to add cancellation coverage, we could have tacked that on to the same plan. Our non-refundable trip costs total $3,000, including cancellation penalties on our rental car, deposits on certain home rentals and fees to redeposit airline points in our frequent-flyer accounts. Insuring against these losses would raise the premium by $116. That cost is still reasonable relative to other providers.

In the course of fact-checking this post, I noticed that when one requests a quote for the ExactCare policy on the Berkshire Hathaway site, it calls for information about trip cost. Unless you enter a zero in that box, you’ll get a quote for the more expensive version of the policy, which includes cancellation. It was another reminder that online sites should just be a starting point. If you don’t see what you’re looking for, call the company and ask.

Deborah L. Jacobs is the author most recently of the five-time award winning book, Four Seasons in a Day: Travel, Transitions and Letting Go of the Place We Call Home, about her adventures — and misadventures — living in France. Follow her on Twitter at @djworking and join her on Facebook here. You can subscribe to future blog posts by using the sign-up box on her website’s homepage.

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