Best Travel Insurance for Frequent Travelers

Best Travel Insurance for Frequent Travelers

First things first: travel insurance is essential if you are a frequent traveler.

This is especially true, if you’re a digital nomad who changes places a lot. You want to make sure that you and your belongings are always covered, wherever and whenever you may decide to go. But how does travel insurance work? What are the important aspects to pay attention to? 

Travel insurance come in packages. These insurance packages differ depending on:

  • Coverage limits
  • Insurance options/types
  • Your date of departure and trip duration
  • Cost of your trip
  • Your age

In this article, I’m going to walk you through some tips and tricks to maximize the efficiency of your insurance. These will include: 

  • What do different policies cover? 
  • How does COVID-19 play into travel insurance plans? 
  • The best travel insurance companies to look at, and much more.

What Should I Insure?

I often get asked when working with digital nomads or frequent travelers, “What should I insure? Should I put down that $3,000-4,000 a year and just get the comprehensive coverage? Do I really need that baggage delay clause? Or should I go with something a bit cheaper and be more careful?”

First and foremost, let me tell you how travel insurance companies work. Their complete business model is based on collecting more insurance premiums than their actual expenses. So, they need to collect enough money to cover claims, marketing costs, personnel costs, expenses, profit margins, and so on. 

This means that they’ll probably try to get as much from you as they can.

What’s the Alternative to Comprehensive Coverage?

I really hate to be the bearer of bad news, but you’re probably paying too much for your insurance services. Now don’t get me wrong, I get that sometimes you just want that peace of mind, thinking, “I have a rock-solid travel insurance plan. Everything I own is insured, so let’s dive in! Headfirst, eyes closed, can’t lose.”

Let’s look at this in a different light, though. Let’s say you go to that trusty travel insurance office in your town, and they draw you up a travel insurance plan with zero deductibles. Now that plan looks impressive! It covers petty theft, lost luggage, your phone, laptop, that old camera that you promise yourself to use every time, the whole nine yards. You look at that annual plan for the premiums, and it’s $3,500. Not too bad, right?

Now take a second, step back, and really look at the annual plan. What really would break your back financially on that list? Your $300 phone getting stolen? Not really. Most probably, it would be the emergency medical services.

Now look at those annual plans and choose the highest deductible that works for you. Let’s say a couple of hundred dollars yearly. It is important to keep in mind that “insurance” is something you hope to never use! So, rather than paying a lot for your annual plans, pay less. Save the difference to pay up in case of the unfortunate event.

You can very realistically, as you’ll see later, end up with a $500 premium! That might seem too little, but stay with me here. Let’s say you take the rest of that money  – $3,000 in our example – and put it in a high-interest savings account. Then you have a net to fall back on in case something happens.

Finding the Right Travel Insurance Policy

Now that I’ve set up what to insure and how to approach insurance services, time to move on. Let’s take a look at the different types of insurance plans available that you should consider for your trip.

Travel Insurance

Travel insurance is usually an umbrella term that covers all types of travel insurance policies. We’ll go through these types in this section. Think of things like car rental insurance, missed flight connection, delayed baggage, and so on.

Some credit card providers include travel insurance for free. You may also benefit from rental car insurance with your credit card, but you must read the fine print.

A lot of travel medical insurance might have some coverage for these things. So if you’re getting travel medical coverage, might as well look for bundles. I’ll mention some of the best travel insurance companies later on.

However, going for travel insurance plans out of your own pocket is often a bad idea. There are many things that you most likely will never use, like a missed connection, for example. I’ve taken over 600 flights in my life, and I think I only had a problem with a missed connection once or twice.

Why Going for Travel Insurance Plans Isn’t Exactly Profitable

Firstly, the chances of something happening are very slim. Even if something happens, it’ll take so much of your time tracking down insurers to pay you what you deserve. You’ll need to file a claim and then wait for reimbursement, which could take weeks.

Secondly, in the case that something happens, it would be much easier to deal with it yourself. If you set up your own “self-insurance” account, as I suggested earlier, you’ll have a safety net.

Lastly, more often than not, you can get compensation from airlines without having a travel insurance plan. So my recommendation is, skip those pesky little insurance details and set up your own fund.

You might be asking, so what sort of travel insurance should I consider?

Travel Health Insurance

Health or medical insurance is probably the most common form of travel insurance. It’s essential to make sure that you have emergency medical coverage abroad.

You don’t want to find yourself over in India or the United States and get into an accident that has to be treated locally. Without emergency medical insurance, that’s just asking for trouble. The medical expenses might run into tens or even hundreds of thousands of dollars.

A decent emergency medical travel insurance should take care of any medical expenses you need locally. Be careful, though, as most travel health insurance is not “primary.” This means that they depend on you being entitled to treatment in a specific location. They’ll often ship you there if you need long-term medical care.

So pay attention to make sure that you have long-term medical coverage treatment in your home country. So if you’re away from home and have to get shipped there, you should be good and covered. This is called “Emergency Evacuation and Repatriation.”

Emergency Evacuation and Repatriation

Sometimes, you might get in an accident and be taken to a medical facility that’s not suited to provide the proper care. In that case, you might need emergency medical evacuation coverage.

So What Are Emergency Evacuation Policies, and Do You Really Need One?

Most travel health insurance policies come with a built-in emergency medical evacuation policy. The local doctor might make the professional decision that the facility you’re currently in isn’t adequate to treat you. In this case, your insurance company’s medical advisor has to transport you to another hospital.

Keep in mind, though, that if you have a stand-alone evacuation policy, you’ll be covered until you get to the new hospital. Once you’re there, however, you’re on your own. That’s why you should pay attention to your medical coverage.

Whether emergency medical evacuation plans are beneficial or not is really up to your travel needs. If you enjoy hiking miles and miles to remote villages, then I would say go for comprehensive emergency medical coverage. On the other hand, if you spend most of your time in large cities in developed countries, it’s not that important.

In any case, if you plan to go somewhere remote, make sure that you have adequate medical coverage one trip. Better safe than sorry.

There’s a wide range of coverage limits on this policy. They start at $25,000 and can go up to millions. Evacuation can get really expensive in extreme cases. This is why I recommend you look at a policy with about $100,000 if you’re traveling to a really remote or undeveloped area.

What You Should Know When You Purchase Travel Insurance Coverage

Picking a travel insurance policy is sometimes tedious work. There are so many plans available, and they all offer different types of coverage. I’ve prepared a list for you to make sure to pay attention to a few points. That way, you can get the best bang for your buck when you purchase travel insurance:

Pre-Existing Conditions

You must be very careful about pre-existing conditions. When taking out a new travel insurance policy, pay attention to the pre-existing conditions clause. This also counts when extending your current policy. Anything that happened before the extension will be treated as a pre-existing condition. This means that it’ll often no longer be covered by most travel insurance companies.

When Will You Actually Be Covered

A traditional travel insurance policy will often only cover you in your home country if you’re a legal resident there. This means that if you’re traveling long-term, that might not be the case.

Moreover, many travel insurance policies will only cover trips of a certain length. This length differs from 30 days and can go up to 90. There are many policies that even require you to have round-trip flight tickets for your insurance to be active.

Finally, if your travel insurance policy is with your credit card, you might need to pay at least 50% of the total trip cost with your credit card. In some cases, you’ll need to pay 100% of the cost of your trip for the insurance to be active.

Home Country Visits

This is an essential one if you’re often away from home. There are quite a large number of policies that limit the number of visits you may make to your home country through the duration of the policy. Pay very close attention to this. Sometimes you can purchase a one-year policy and have to pay a few visits to your home country for some reason. In that case, the rest of the policy will be canceled without any refunds.


There are two types of deductibles you can have with your policy, “per incident” or “per period.” You want to try and go for “per period” deductibles. This means that if you pay the deductible once, you don’t have to pay it for the rest of the period.

Types of Coverage

The different types of coverage in your travel insurance plan are basically endless. I’ll list some different types of coverage in this section and explain some of them. Some of those tend to be self-explanatory, such as “trip cancellation coverage,” for example. The various types of coverage are:

  • Medical coverage
  • Trip Delay coverage
  • Evacuation coverage
  • Trip Interruption coverage
  • Adventure sports coverage
  • Trip cancellation coverage

Trip Delay Coverage

Delay coverage works in various ways. For example, delay coverage would reimburse you if you had to stay in a hotel because of a trip delay by the airline. Many people have some misconceptions about delay coverage. You won’t be reimbursed if you decide to delay your trip on your own. There has to be an unforeseen cause.

Adventure Sports Coverage

This type of coverage takes care of Adventure Sports mishaps. What does adventure sports mean? Well, think about scuba diving or kite surfing, for example. Sometimes doing such activities is in your trip plan. In this case, it’s smart to have adventure sports coverage, just in case.

Trip Interruption Coverage

Sometimes people mix trip cancellation and trip interruption coverage. Trip interruption means that you go on your trip, but it gets cut short due to illness, for example. Trip cancellation, however, means that you can’t even go on your trip due to an unforeseen issue.

Which Travel Insurance Providers Works Best For You?

In this section, I want to recommend the top travel insurance providers for you. However, I would advise you to go and do a bit of research yourself. First, I’ll present you with a few sites so you can compare travel insurance plans and insurance services.

Travel Insurance Comparison Sites

Looking for the right travel insurance provider can take hours of research. To make your life easier, here are a few sites where you can compare the travel insurance coverage plans available.

This website has about 15 different travel insurance providers from which you can compare. You can also see customer reviews for each insurer, ask for quotes, and have access to a big number of articles and tips.

This website has about 60,000 customer reviews. They also have a service called “Anytime advocates.” This service provides global assistance. They can help you with the insurance claim process and how to appeal denied claims.

You can compare about 30 different travel insurance plans on this website. There’s also a section called “Travel Insurance 101,” which is really helpful in explaining the policies and benefits of specific plans.

This website has a unique policy called “Zero Complain Guarantee.” They will remove any provider if a customer complaint isn’t resolved satisfactorily.

Best Travel Insurance Providers

IMG Travel Health Insurance

This company focuses on health insurance and doesn’t include any non-health-related benefits. They’re popular because they’re quite economical. You might have some problems with slow claim handling as they tend to take their time.

What IMG can offer is flexible deductibles and cheap cost for renewing or extending your policy. On the other hand, the deductibles are only payable once every 12 months.

Keep in mind that this is a Health only policy, which means things like travel delays are not covered. Additionally, they don’t always support direct billing. Direct billing means the hospital or doctor billing them directly. This means that sometimes you might have to pay the doctor directly and then wait for your claim to be processed to be reimbursed.

Below you’ll find the average pricing for a single traveler who is 35 years of age. This is for travel health insurance only, $500,000 limit with a $250 deductible:

Travel DurationWorldwide CoverageWorldwide coverage excluding the US
One Week$19$10
Four Weeks$76$39
52 weeks$504$972

True Traveller

True Traveller is climbing it’s way up the list of top travel insurance providers, especially in the UK. Their insurance is valid for residents of the UK and countries in the EEA (European Economic Area)

They have fairly cheap plans. Though these plans include basic coverage, you can choose to add extras. But, that can increase your premiums by quite a bit.

One of the benefits of True Traveller is that they don’t have any limitations on home visits. Keep in mind though, that you’re not covered by their plan when you’re in your home country. Additionally, they’ll often arrange direct billing for medical treatment that costs more than £500. Below that, you’ll usually have to pay the doctor directly and then get reimbursed later.

The downside is they are only available for EEA residents. Having an extension is also pretty costly with True Traveller. Moreover, the extras can really make or break the plan. A seven days policy, for example, can start at £34 and go all the way to £361 depending on the extras. Below is a table with their average prices for a mid-range package, with zero extras and a £75 deductible per claim.

IMPORTANT NOTE: The prices below were converted from GBP on 21 October 2020 and may vary:

Travel DurationWorldwide CoverageWorldwide coverage excluding the US and Canada
One Week$62$55
Four Weeks$126$111
52 weeks$462$551


Saving the best for last, I want to tell you about SafetyWing. This is a relatively new player on the scene, but they’re coming in strong. In my opinion, they take first place on the top travel insurance companies list. Their ultimate goal is to create insurance that is independent of any country. Designed especially for freelancers and digital nomads.

They have a lot of various plans for insurance, even primary healthcare services in some countries. The package that I’ll be talking about is called the “Digital Nomad Travel Insurance.”

What’s excellent about this package is that it supports recurring billing. Basically, you become insured in the form of a subscription, which you can stop at any time you wish. They also shine in being the cheapest on this list. For worldwide coverage, excluding the US, you’ll pay around $42 monthly. 

Moreover, they support direct billing to most hospitals. They have excellent medical evacuation coverage and cover most private emergency medical care. Additionally, their global assistance is excellent.

The downside of SafetyWing is that their policy covering the US is a bit expensive in comparison to other policies. However, as it’s a subscription, you can switch between policies with ease. Below you’ll find the average pricing for a traveler who’s 35 years of age:

Travel DurationWorldwide CoverageWorldwide coverage excluding the US
One Week$19.18$10.49
Four Weeks$76.72$42
52 weeks$983$538

Some Other Providers Worth Looking Into

Allianz Travel Insurance

Allianz Travel Insurance is a decent insurance company, though their premiums tend to be a little high. They’re also not available in every country, so you might want to check their website first. They do, however, require you to purchase insurance before departing on your trip. This might be a plus for some and a minus for others. You can check the Allianz Travel Insurance website for more information.

AIG Travel Guard

AIG Travel Guard is one of the largest insurance companies in the world. They’re based in the United States and usually offer insurance with credit cards. AIG Travel guard can offer various plans depending on your needs, though they tend to be a bit on the pricey side.

The prices really change depending on your home state, age, and how much you paid for the trip. For example, a 40-year-old man who is traveling to Europe and spending $5,000 will get the “Essential Package” for about $255 and the “Deluxe Package” for $337. Their website is easy to use, and you can get your quotes fairly quickly.

Seven Corners

Seven corners mostly focus on travel insurance plans in the Schengen area. If you’re a non-EU citizen and have a plan to travel to the Schengen area, you might want to look at Seven Corners.

Travelex Insurance Services

Travelex Insurance Services is a company that has been providing coverage for 55 years. They offer the ability to request a plan change during your insurance period, which might come in handy.

Berkshire Hathaway Travel Protection

Berkshire Hathaway Travel Protection is a company specializing in travel insurance in North America. If you’re traveling to Canada or the US, they have unusually fast claims payments. However, they’re currently experiencing some delay on those.

Travel Insurance Amid the COVID-19 Pandemic

The coronavirus has altered the whole infrastructure globally, especially travel. In this section, I’ll briefly share with you some information on travel insurance during the pandemic. How to stay safe and, hopefully, avoid changes in your travel plans.

Is COVID-19 Covered by Insurance?

Unfortunately, most insurance policies exclude epidemics or pandemics. This means that any expenses on your travel caused by the novel coronavirus aren’t going to be covered. You need to check with your current provider to be certain before you hit the road.

The good news here is that SafetyWing introduced coverage for COVID-19. They also often cover the PCR test if a doctor deemed it necessary.


Which Insurance Options Should I Choose On My Plan?

This really depends on what kind of coverage you need, want, or expect. Below are a few examples of wants and needs and what plan covers those:

Travel Medical Coverage


This will cover payments of medical and dental expenses if you get sick or injured on a trip. This is, of course, provided that your emergency treatment is not covered by your regular medical and dental health insurance plan.

Emergency Evacuation and Repatriation

Emergency evacuation and repatriation include coverage of the expenses of transportation to the nearest hospital. They might even cover the flight home in case you get sick or injured on your trip.

“Cancel for Any Reason” Coverage

Cancel for any reason coverage plans include reimbursement of nonrefundable reservations for any reason you choose to cancel a trip.

The difference between cancel for any reason and trip cancellation is simple. Under trip cancellation, you’ll only be covered if your trip gets canceled because of some unforeseen event, such as illness or an accident. This is why trip cancellation usually tends to be cheaper.

Trip Delay Coverage, Trip Cancellation Coverage, and Trip Interruption Coverage

This will provide coverage in the cases where you have to cancel or end a trip early. Additionally, it’ll also provide coverage of extra expenses in case your trip is delayed by the airline, for example, lodging in a hotel.

Baggage and Personal Belongings

This insurance coverage will take care of payment for lost, stolen, or damaged luggage. It may also cover baggage delays in some cases.

Travel Assistance

This type of travel insurance provides various travel assistance services. These include finding a lawyer abroad, for example.

What Does “Travel Select Plan” Mean?

A travel select plan is usually a basic travel insurance plan. With travel select plan, you can expect some decent coverage at a low cost.

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