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Annual travel insurance for frequent travelers (multiple trips)

If you're traveling in 2021, check which travel insurance covers COVID-19 (test and treatment abroad).

Annual travel insurance is the most convenient option for frequent travelers who want to travel without any worries and save some money at the same time.

Of course, before you buy annual travel insurance, make sure that it’s your best option. In my case, for example, there is no doubt about it, since, due to my work, I have to travel to South America at least once a month, so I can save a ton by buying annual multi-trip travel insurance.

In addition to these business trips, every time I take vacation, I travel abroad, and if I have a few days off, I take a little getaway trip.

Annual travel insurance to travel protect 365 days

Annual travel insurance for frequent travelers

As you can see, I’m a frequent traveler, so eight months ago, I decided to buy multi-trip annual travel insurance and stop spending money on insurance for each individual trip.

I know that this is the best option for me, and later on, I’ll tell you about my experience, but now I want to help you figure out if annual travel insurance is the most suitable option for you.

Annual multi-trip travel insurance

In this comprehensive guide to annual travel insurance, you’ll find:

I have also created an annual travel insurance comparison among the best providers for multiple travel insurance. But before going there, you must first know that yearly travel insurance with 365-day coverage is not the same as long-term travel insurance.

The first one is insurance for frequent travelers, that is, it covers all the trips you take in a year with a limit on days per trip, while the second one covers you every day of a long-term trip that can last a year or even longer. For example, I have a Heymondo policy that covers trips of up to 120 days during a year. However, most annual multi-trip insurance providers cover trips of up to 60 or 90 days.

How to hire travel insurance yearly?

Annual multi-trip travel insurance

As you can imagine, each of these insurances focuses on a different type of traveler, and you have to know what kind you are to see if annual plan travel insurance is the best option for you.

What is annual travel insurance?

Annual travel insurance is an insurance that covers each and every one of the trips you take within one year.

This is frequent traveler insurance; therefore, it’s convenient for someone who, for example, takes several short trips a year and maybe a couple of long trips, whether for leisure, business, or other reasons.

Whatever your case, if you consider yourself a frequent traveler, you will save a lot of time and money by buying annual medical travel insurance instead of purchasing individual insurance policies for each trip.

Who is multi-trip annual travel insurance for?

The following types of travelers often discover great benefits from purchasing annual travel insurance:

  • Travel addicts who take every opportunity they have to travel.
  • Couples in long-distance relationships who travel often to see each other.
  • Sales team members that visit clients from time to time or attend fairs and shows in different countries.
  • Athletes participating in international events.
  • Members of associations that attend events periodically throughout the year.
  • Photographers, international journalists, travel bloggers, etc.
  • International students, who return home at least every four months; it can also be beneficial for them to buy travel insurance with 365-days-a-year coverage.
  • Expats or international workers who return home every four months or less.

If you’re an expat or international worker, annual travel insurance can also save you a lot of money. However, you should keep in mind that you will have to return home from time to time to extend your coverage.

In other words, don’t plan to use annual travel insurance to take a gap year and travel the world, away from home, nor to work abroad and not come back home for a long time.

How does annual travel insurance work?

When purchasing annual multi-trip insurance, you have to pay attention to three factors: the coverage it offers, the price, and the maximum days of coverage for each trip.

When you leave your home country for your next destination, the day counter is reset and the covered days start to run out. That doesn’t mean you can’t travel longer than what is stated in your policy; however, you will only be covered for the number of days specified in your policy.

Compare quotes for annual travel insurance

How does annual travel insurance work?

For example, my Heymondo annual multi-trip insurance covers trips of up to 120 days, but if I travel for 128 days, the last eight won’t be covered by the policy. I would have to come back home and leave again for the maximum days counter to reset to zero.

To control this, every time you use your annual travel insurance coverage, you need to show a supporting document that shows the start date of your last trip to check if you are covered. The plane ticket itself can serve as proof.

But don’t worry; you don’t have to notify your insurance provider every time you take a trip. You only have to show the proof of departure date when you need assistance from your insurance.

Advantages of Annual travel insurance (Multiple international trips within one year)

One of the biggest advantages of annual travel insurance is that you don’t need to remind yourself if you have insurance until the day you need to use it. You won’t have to go through the purchase process every time you leave the USA.

Another benefit of multiple travel insurance, if you are a frequent traveler, is that you will save a lot of money compared to buying individual insurance policies for each trip.

Also, most importantly, wherever you go you will always be covered and protected in case of any unforeseen event.

However, when considering purchasing annual travel insurance, it is important to know how it works to avoid misunderstandings and later problems. Above all, it is important to be clear about the maximum number of days per trip.

Compare Annual Travel Insurance Plans

In this section, you will find an annual travel insurance comparison so you can check the prices and coverage of the main multi-trip insurance providers and decide which insurance plan you want to get.

To carry out the comparison, I have run simulations on the websites of the different insurance companies and used the same data in all of them: US citizen taking multiple trips worldwide within a year.

Some companies have several annual travel insurance plans, so in those cases, I have chosen the one with the lowest price that covers at least USD 50,000 in medical expenses. This way, you can also get an idea of the cost of annual travel insurance.


Heymondo Annual Multitrip

Travel Guard Annual Travel Plan

Allianz AllTrips Prime


USD 173.14

USD 259.00

USD 500.00

Max. Days per Trip

120 days

90 days

90 days

Medical Assistance

USD 100,000

USD 50,000

USD 50,000


USD 500,000

USD 500,000

USD 250,000


USD 60,000

USD 50,000

USD 50,000


USD 60,000

USD 50,000

USD 50,000

Damaged luggage and theft

USD 2,500

USD 2,500

USD 1,000

Trip Interruption

USD 4,500

USD 2,500

USD 5,000


What is the best annual travel insurance for frequent travelers?

Once you have checked the comparison tab, I’m sure you’ll understand why I decided to buy Heymondo annual multi-trip insurance: it has the highest coverage and maximum number of days per trip, and the price is lower than all the other annual multi-trip insurance plans.

However, that is not the only reason why I chose Heymondo when I bought my multi-trip worldwide travel insurance.

Thanks to its app, you don’t have to worry about taking your multi-trip insurance policy with you on every trip you make during the year. You’ll have all the information on your phone and be able to chat with a doctor just by pressing a button.

Heymondo the best annual multi trip travel insurance

What is the best annual travel insurance for frequent travelers?

I personally have already had to use the app several times this year, and the assistance has always been excellent. Minor doubts can be resolved by chat, and if you need to see a doctor in person, you can call and find out where the nearest hospital is for free.

The best thing is that when you get to the hospital, Heymondo will have already taken care of arranging the payments, so you won’t have to pay anything. You will not have to advance a single dollar. There are no out-of-pocket expenses with Heymondo.

Do you want to get Heymondo’s annual travel insurance policy for frequent travelers? You can get 5% off your annual multi-trip insurance for being our reader.

How much is annual travel insurance?

With Heymondo you will be covered on all the trips you take in a year for only $173.14 or €155,23. If you want to get coverage for your electronics, it will cost $190.47 or €170,76. Are you doing any extreme sports? Then the annual multi-trip travel insurance will cost $225.09 or €201,80.

However, buy your travel insurance today and you will get 5% off! You can select when you want your coverage to start, and it doesn’t have to be today. Is your first trip of the year in two weeks? Then your coverage will cover you 365 days from then.

How much can you save with an annual travel insurance plan?

To check if it is worth buying an annual multi-trip travel insurance plan, input information for the different trips you have in mind for the upcoming 365 days and get the price from the Heymondo website. Let’s try some examples.

Imagine that you are going to take several trips during the next 365 days and buy individual travel insurance plans:

  • Indonesia (2 weeks) – $ 61.87
  • Iceland (4 days) – $ 22.78
  • Spain (1 week) – $ 33.37
  • Morocco (3 days) – $ 15.52
  • United Kingdom (5 days) – $ 22.78
  • Norway (4 days) – $ 22.78
  • Brazil (1 week) – $ 33.37
  • Mexico (1 week) – $ 33.37
  • Argentina (1 week) – $ 33.37

If you pay for these policies individually, it would total $279.21.

If you instead buy the annual travel insurance plan, you would pay $173.14. In other words, you would have all those trips covered, and you could take even more trips without paying any other fees as long as the trips don’t last more than 120 days in a row outside your home country.

How much does multi-trip annual insurance cost?

How much can you save with an annual travel insurance plan?

As you can see, if you are a frequent traveler, purchasing annual international travel insurance would be very convenient for you and allow you to save money without losing the benefits of the best travel insurance providers.

You can use examples to get the prices for individual travel insurance policies yourself on the Heymondo website to check if annual travel insurance suits you and if it is worth it based on your current travel frequency.

What does multi-trip travel insurance cover?

I have already mentioned the great coverage of the annual travel insurance that Heymondo provides, so it’s time to tell you exactly what it’s all about.

  • Medical expenses. It covers up to $100,000, including care provided by emergency medical teams and specialists, complementary medical examinations, hospitalizations, treatments, surgical interventions, and medicines.
  • Luggage theft and damage. It covers up to $2,500 in case of robbery with violence, the carrier losing all or part of your luggage, or damage caused as a result of a fire or aggression during the trip. It includes the search, location, and shipment of lost luggage.
  • Early return and repatriation. In the event of an accident, illness, or death, the insurance covers all the travel expenses to take you home for up to $500,000.
  • Transportation costs of a relative in the event of your hospitalization or death. In either of these two cases, the expenses of the round-trip ticket and the stay of your relative are covered, with no limit.
  • Additional compensation for accident. Up to $60,000 in case of permanent disability or death by accident.

In addition to these basic annual travel insurance coverages, there are other optional coverages that may be interesting to you: adventure sports coverage and electronics coverage.

What’s usually excluded from annual trip travel insurance?

Don’t forget that there are some exclusions for annual travel insurance.

The most important is the maximum days of coverage you have for each trip, since if you take a longer trip, you won’t be covered by your multi-trip insurance for the last few days. In other words, if you buy Heymondo multiple travel insurance and have an accident on the 121st day of your trip, you won’t be entitled to any assistance or compensation.

Remember to always carry supporting documents or receipts from the moment your trip begins so that you do not have problems when requesting insurance assistance (plane tickets, train tickets, etc.).

This leads me to point out something important: you won’t be covered during car trips. You will need a plane, train, or bus ticket, or a stamp on your passport, to prove the start of your trip. For example, if you travel from New York City to Niagara Falls by car, you would have no way to prove the exact day your trip started, and therefore. you would not be covered by your annual travel insurance for frequent travelers.

How to get a cheap annual travel insurance policy

If you want to purchase Heymondo annual travel insurance, it’s very simple. Go to its website, on “get a quote”, and select “Multiple trips in one year”.

annual multitrip travel insurance how to get a quote

Then, specify your country of residence. Your multi-trip travel insurance will have worldwide coverage.

Heymondo holiday insurance annual

In the next step, you will have to indicate when your first trip starts. From there, you will have 365 days of coverage. Leave your return day blank. Heymondo will automatically mark the last day you will have coverage.

multi trip insurance coverage

You will then have to select the number of travelers and provide emails for them.

One year travel insurance Heymondo

And, finally, the price of your insurance will appear. This price doesn’t include coverage of electronics or adventure sports.

Heymondo discount annual travel insurance

As you can see, the price of Heymondo insurance is $173.14, but as a Capture the Atlas reader, you will get a 5% discount.

In case you need it, before confirming the purchase, you can add additional coverage, such as electronics or extreme sports. In this case, a fee will be added.

Travel insurance for multiple trips review

As I told you at the beginning of this article, I bought this annual travel insurance eight months ago, and I have already had to use it a couple of times.

American Airlines canceled a flight, and I had to spend two days at the Chicago airport. Luckily Heymondo took care of all the hotel and food expenses during that time. I sent them the invoices for the expenses incurred, and after two weeks, they reimbursed me for the full amount.

On another occasion, during my trip to Costa Rica, I cut my leg on some coral. Heymondo took care of all the expenses at the medical center where they took care of me. I didn’t have to worry about anything, including the payments.

Before I had this annual multi-trip insurance policy, I used to buy the Heymondo travel insurance for individual trips, as there is no doubt, it’s the best travel insurance. I have also had to use it in some difficult situations.

Best multi trip travel insurance reviews

Travel insurance for multiple trips review

For example, when a monkey bit me in Bali. I bought my Indonesia travel insurance with Heymondo, and the chat assistance worked perfectly. They assisted me very quickly and let me know which hospital I had to go to, and when I arrived there, I received all the treatment with no out-of-pocket expenses. If you want peace of mind, there is no better or cheaper option.

Therefore, I cannot recommend them enough. If you are a frequent traveler, annual travel insurance is the best option for you, and Heymondo is the provider with the highest coverage, lowest price, great travel assistance thanks to its app, and no out-of-pocket expenses.

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Hi, I'm Ascen, a globetrotter based in Philadelphia, USA. I enjoy exploring new landscapes and creating in-depth travel guides for Capture the Atlas.

I have felt a special connection with nature and all the inhabitants of the planet since I was a kid. I am passionate about discovering new countries and especially their wildlife, but no matter how many places I visit, I will always belong to the remote beaches of Almería, in Southern Spain.

You can know a little more about me here.

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One thought on “Annual travel insurance for frequent travelers (multiple trips)

  1. BJ BOLTAUZER says:

    Hey there,
    we are interested to purchase annual multitrip medical emergency travel insurance with specific COVID-19 cover rider. We are seniors, my DOB is April 20, 1946 and my wife’s is October 23, 1950. We reside in Canada and woud like to travel to Costa Rica in October 2020 and to Europe in 2021, if COVID-19 pandemic situation will permit.
    Your advice would be much appreciated.

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