Should You Buy Travel Insurance?

You’ve saved for months or years for that fantastic cruise or resort stay.  You’re packed and ready to go – and then disaster strikes.  A close relative becomes ill.  You fall and injure yourself.  Or you’re already on the road and the plane has a mechanical problem, causing you to miss a day or two of your trip.  Your luggage winds up in Toledo, Ohio and you’re in Toledo, Spain.  Or – worst of all – you need medical attention while on your trip and your own health insurance won’t cover you.

Should You Buy Travel Insurance? is a good question. But how you buy it is also important.

Many travel agencies and web site will offer you a travel insurance package as an add-on to your vacation. You book your cruise and then you’re pressured to purchase an insurance package.  Out of fear, you go ahead and agree. But should you purchase one of these plans without being able to truly compare the benefits and costs?

NO!

While many of these packages are probably fine, they are almost certainly requiring you to pay for things you don’t need.  These one-size-fits-all packages cover a lot, but they are also relatively pricey, and unless you do your homework, you may not really be covered for the things that most apply to you.

At Cowboy Concierge, we recommend you purchase your own travel coverage, apart from your booking.  This gives you time to research the offerings from various vendors, crafting a package that works best for you.

Ten Reasons Why You Need Trip Protection Insurance.

1. Airline travel is unpredictable. You can easily find yourself dealing with a mechanical issue or a weather delay. Quality trip protection plans provide reimbursement for covered expenses in the event your travel is delayed due to a defined hazard.
2. Luggage. Trip protection plans cannot guarantee that your luggage will arrive undamaged, but they can help give you the peace of mind knowing that you have coverage that may help cover certain expenses if the airline or common carrier does not return your luggage in the same condition.
3. Medical expense coverage.  We’re all human, and we can all make silly mistakes.  A little slip by the pool and suddenly you’ve sprained an ankle, or you eat from the wrong food stall and wind up in the hospital dehydrated and in trouble. Though your medical plan may still cover these expenses, often hospitals require an up-front payment before they will proceed with services. Some insurance plans can fund these up-front costs quickly and efficiently. 
4. Emergency Evacuation services. Then there’s the truly life-threatening situations where you need to get more intensive care than your beach resort can provide. A good trip protection plan provides emergency medical evacuation coverage that pays for transportation costs to help get you to a hospital where you can receive the care you need.
5. Home life still goes on.  While you’re out sunning or sailing, things can happen back home that require you to return immediately.  Having a trip protection plan can provide reimbursement for your return flight home in the event of a covered incident that forces you to interrupt your trip.
6. Without medical coverage, receiving medical care in certain countries may be a challenge and payment may be required upfront! When traveling to countries such as Egypt or Turkey, it is a good idea to have a travel protection plan in the event you require medical treatment. You can check the U.S. Department of State website to see if they suggest purchasing supplemental coverage for travel to a country on your itinerary.
7. Cancellation. You have to have a last minute surgery, a relative unfortunately passed away, the airline you are scheduled to travel on is on strike; you are not exempt from having unforeseen events arise that can cause you to have to cancel your trip. Purchasing a trip protection plan in advance can help ensure that you have coverage if you have to cancel your trip due to a covered event.
8. Automobile Rentals. Dwaine and I drove from Amsterdam to Ansbach, Germany, and while the drive was lovely, maneuvering the autobahn was a bit nerve-wracking.  Every day driving in the States is hard enough – imagine driving in a foreign country, with different rules, streets and even a different steering wheel! Trip protection coverage often has an optional benefit of car collision damage provides coverage in case you are involved in a car accident while driving in a foreign country.
9. Whether you are travelling with children or on your own, you never know when you may need medical assistance. According to the European Centre for Disease Prevention and Control, in most European countries, you must first visit a doctor’s office before you can purchase an antibiotic. Quality trip protection plans include non-insurance assistance services which will help refer you to local medical providers and pharmacies.
10. Peace of Mind.  The best trip protection plans have a non-insurance concierge service, which can provide assistance when you need to clarify doubts or help you in a dilemma that you may have during your trip – including any last minute recommendations while traveling.

Should You Buy Travel Insurance? Here are the 2026 Top Five Companies:

Based on current 2026 data across coverage breadth, financial strength (AM Best ratings), company longevity, and customer reviews (Trustpilot/BBB), here’s the top five travel insurance providers today:

1. Allianz Travel Insurance (Allianz Global Assistance) — Backed by Allianz SE, one of the world’s largest insurers (founded 1890, operating in 70+ countries). Its US brand traces to Access America (1983). Comprehensive plans covering cancellation, medical, evacuation, and CFAR add-ons; rated “Great” at 4.1/5 on Trustpilot. Financial backing is arguably the strongest of any provider in the category.

Allianz Travel Insurance: https://www.allianztravelinsurance.com

2. Travelex Insurance Services — Founded 1996, underwritten by Berkshire Hathaway Specialty Insurance (A++ AM Best) with newer policies moving to Zurich American (A+). U.S. News ranked it the #1 travel insurance company of 2026 out of 45 evaluated, and it holds a 4.4/5 on Trustpilot. Offers tiered comprehensive plans from budget to premium.

Travelex Insurance Services: https://www.travelexinsurance.com

3. AIG Travel Guard — One of the oldest dedicated travel insurers in the US, founded 1982. Acquired by Zurich Insurance Group in December 2024, giving it strong financial backing. Broad comprehensive coverage across trip cancellation, medical, and baggage, though claims-process complaints show up more often in reviews than with peers.

AIG Travel Guard: https://www.travelguard.com

4. Seven Corners — Founded 1993, underwritten by carriers rated A+ (Superior) by AM Best. Particularly strong on medical and international/expat coverage. Consistently earns some of the best customer ratings in the industry — 4.5/5 on Trustpilot.

Seven Corners: https://www.sevencorners.com

5. WorldTrips — Underwritten by Tokio Marine HCC subsidiaries carrying an A++ (Superior) AM Best rating — the single highest financial-strength rating of any major travel insurer reviewed in 2026. Its Atlas plans are comprehensive and well-regarded, making it the strongest pick if financial security is your top priority.

WorldTrips: https://www.worldtrips.com

(A note on trade-offs: no single company wins on all four criteria simultaneously. Allianz and Travelex balance all four best overall; WorldTrips and Seven Corners lead on financial strength and customer satisfaction respectively but are less known brands; Travel Guard’s longevity is offset by more mixed claims-service reviews.)

Our COVID Experience

During COVID, we were on a river cruise through France with Viking Cruise Lines. We had a wonderful time, even though we were routinely tested for COVID on the ship. We tested all clear every time . . . until the very last day before we were to return home.

I was the guilty one. Somehow I’d managed to pick up the bug and there we were – stuck in France missing our flight home and looking at five days of isolation in Paris!

Not to worry. I simply produced my trip insurance information and we were good to go. They paid for everything . . . our room, our food, our re-booking fees. It was all taken care of! We were so happy we’d invested in a quality travel insurance plan!

Should You Buy Travel Insurance? Questions and Answers

Is travel insurance worth the extra cost?
For most trips involving flights, cruises, or international travel, yes. The cost is small compared to what you’d pay out of pocket for a missed connection, a medical evacuation, or a canceled trip due to illness or a family emergency.

Should I buy the insurance offered when I book my cruise or resort?
Not automatically. These bundled packages are convenient but often overpriced and packed with coverage you don’t need. Cowboy Concierge recommends buying a separate policy so you can compare providers and tailor coverage to your actual trip.

Does travel insurance cover medical expenses abroad?
Many plans do, and some can fund upfront hospital payments quickly—important since many countries, including Egypt and Turkey, require payment before treatment. Check the U.S. Department of State website for country-specific guidance.

What’s the difference between travel insurance and a non-insurance concierge service?
Insurance reimburses covered losses (cancellations, medical bills, delays). A concierge/assistance service, included with many quality plans, helps you find local doctors, pharmacies, or resources in real time while traveling.

Which travel insurance company is best in 2026?
It depends on your priority. Allianz and Travelex rank highest overall for balancing coverage, financial strength, and reviews. WorldTrips leads on financial backing (A++ AM Best), and Seven Corners leads on customer satisfaction.

Should You Buy Travel Insurance?

We at Cowboy Concierge highly recommend travel insurance. But if you’re booking a trip to a resort or a cruise, don’t be pressured into purchasing the first package they throw at you.  Check out the websites above and find the one that works best for you.

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