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Yearly travel insurance vs single trip: which one is better?

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Annual vs single trip travel insurance: which one is better?

Annual travel insurance or take it out every time? There are few who could beat the bum for number of trips [...].

Yearly travel insurance vs single trip: which one is better?
by Nick V.
May 10, 2025

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Annual travel insurance or take it out every time? There are few who could beat the bum for number of trips during the year.

In this article:

    However, there is still a large number of people who make several trips throughout the year, whether for business or purely for fun. We all know beyond the number of trips taken during the year, How important travel insurance is when you find yourself outside your home country's borders. Whether it's an unforeseen medical emergency thousands of miles from home, a canceled flight, or lost luggage, having the right coverage can mean the difference between a manageable inconvenience and a real disaster.

    Today, companions offer products highly customizable with annual travel insurance gaining increasing market share. But are these kinds of policies really cost-effective compared to single-trip insurance policies that have to be taken out each time for the next trip? I would like to try to make a comparison between the two solutions. To do this I will use the following as a reference company Heymondo, including the 10% discount of which TFC readers.  can take advantage of on all products of this insurance company.

    Annual travel insurance

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    Annual travel insurance is the "all inclusive" solution for those who are always packing a suitcase. Once taken out, the policy Covers all trips made within one year, with some limits on the duration of each trip. In the case of the Heymondo multi-trip. each covered stay abroad is at the maximum of 60 days. After this period has expired you are out of coverage but you only need to return home even for a handful of hours and leave again to be insured again. Obviously, the annual multi-trip policy was not created for the purpose of being insured for a period longer than 60 days. In this case the Heymondo policy to consider would be the Long Stay policy to which I will devote an article soon.

    In terms of price, Heymondo offers. A rate that does not consider the age of the contractor and therefore the price is the same for everyone. The Heymondo multi-trip policy is underwritten up to the age of 74 years. It is offered in two versions that differ in the maximum limits for each of the events covered.

    The annual policy Multiviaggi Top, with a ceiling of 5 million in case of medical expenses, is offered at 151.98 with the TFC discount already applied.

    As for the other version, called Premium multi-trip, which has a ceiling of 10 million, the price is 171.77 with discount already included.

    Other differences between the two versions of the policy are in the ceilings disbursed in case of an event. For the Premium version, almost every limit is double that of the Top. Both policies are customizable by selecting items of interest such as the coverage for electronic and adventure sports equipment. Heymondo provides a deductible of 75 euros by default but that can be removed by adding the modest sum of 7 euros to the cost of the policy.

    The main advantage of annual travel insurance is first and foremost the convenience: once activated, there is no need to think about taking out new policies every time you leave. In addition, as the number of trips in the year increases, the cost per single tripor decreases, making this a potentially very inexpensive solution. Coverages are comprehensive, including medical care, medical repatriation, baggage protection and liability.

    Single trip policies

    The classic alternative is the single trip insurance, designed to cover a single trip with predetermined start and end dates. The cost varies greatly depending on factors such as destination, duration and required coverages. Typically, they range from as little as 15-30 euros for short trips in Europe to much larger amounts for long stays in countries outside Europe.

    In the specific case of Heymondo the single trip policy is offered in three variants which differ, as in the previous case, in the maximum amounts with regard to each event. The policies are respectively called Single Trip Tranquilityà, Top and Premium. The ceiling for medical expenses of these three products is 1, 2 and 4 million respectively.

    Let's try some examples By linking to the company's official website. Making a quick quote request for a week-long trip to Europe, the cost for one person ranges from a minimum of 17.91 euros to a maximum of 26.93 euros with the TFC discount already applied.

    For a journey of Two weeks in other parts of the world Selecting "World excluding U.S. and Canada" from the quote request form produces results that range 37 to 58 euros. If, on the other hand, we also include North America then we go to the range between 42 and 66 euros. Prices are doubled by selecting a 4-week stay, and you can already see that the economic difference with the annual policy tapers off.

    Again, the single travel policy is underwritten up to age 74 of age if the trip is up to 60 days otherwise it drops to 54 for longer trips.

    The main advantage of single trip policies is the customization: it is possible to tailor coverages to the specific needs of each trip. For example, for a weekend in a European capital a basic policy might suffice, whereas for a mesand trekking in Nepal it will be appropriate to add specific coverages for high-risk activities and higher ceilings for medical care.

    In addition, single-trip policies have no preset duration limits: you can insure trips of any length, paying proportionately, of course. This makes them ideal for those who alternate between settled periods and occasional but extended trips.

    We take the calculator

    To figure out which option is more cost-effective, it is useful to do an analysis based on the number and type of trips planned in the year. In general, the tie point lies between 3 and 5 trips per year. However, it varies significantly depending on the destination and duration of the trips.

    Let's consider a concrete example: for a traveler who makes mainly short-term trips, a  Heymondo annual policy  151 euros becomes cheaper than single 30-euro policies as early as the fifth trip. If, on the other hand, trips include destinations outside Europe, where a single policy can easily cost 40, 50 or more euros, the break-even point is reached as early as 4 or 5 trips.

    La average travel time greatly affects this assessment. Those who make frequent business trips of only a few days will benefit most from an annual policy, while those who travel infrequently but for extended periods will probably save with single trips.

    Factors to consider in annual travel insurance

    In fact, it is a question of whether it is possible planning trips in advance that will be made during the following calendar year. Probably a mix of short trips to Europe and one or two longer trips to non-European destinations is already enough to be at break-even point or already in profit, preferring annual travel insurance.

    A business traveler who visits clients in Europe every two weeks will have different needs than someone who takes a couple of vacations a year but of long duration. It is not just a matter of frequency, but also of predictability: If your travel plans are subject to frequent change, the flexibility of multi-trip insurance can be invaluable.

    La type of trip greatly influences the choice. Business travel tends to be more standardized in terms of risks and needs, making annual travel insurance particularly suitable. Leisure travel, especially if it includes special activities such as winter sports, diving, or hiking in extreme environments, may require specific additions that are more easily customized in single trip policies.

    The composition of the travel group is also relevant. The annual family policies can be extremely convenient for nuclei that frequently travel together. They become less advantageous if only some members participate in certain trips.

    Essential coverages for frequent flyers

    Regardless of the type of policy chosen, there are certain coverages that no frequent traveler should overlook. Emergency medical care and medical repatriation are probably the most important, with limits ideally no lower than aqualche million, especially for intercontinental travel.

    La protection for cancellations and delays becomes crucial for frequent travelers, especially during periods of climatic or geopolitical instability. A good policy should cover not only the direct costs of canceled travel but also incidental expenses such as hotels and local transportation that have already been booked.

    For those traveling with professional equipment or expensive devices, theluggage insurance with appropriate limits is critical. Frequent flyers should pay particular attention to per-item limits and reporting procedures, which are often stringent in terms of timing and required documentation.

    La third party liability is often underestimated but can prove lifesaving in the event of unintentional damage to people or property during travel. Maximum limits should be especially generous for travel to countries with legal systems that favor high claims, such as the United States.

    The final advice

    The choice between annual and single trip travel insurance has no universally valid answer, but depends on the individual traveler profile. In general, the annual policy is cost-effective for those who carry out at least 4-5 trips per year, especially if of short duration and with standard coverage requirements.

    Single trips remain the preferred solution for those who travels occasionally, for those who need very specific coverages related to particular activities or destinations, and for those who take long-term stays that would exceed the time limits of annual policies.

    The most valuable advice is to Re-evaluate their insurance needs periodically. Ideally at each annual policy renewal or before a significant trip. Travel habits may change making it necessary to update your coverage strategy. Investing time in finding the right solution for your needs is never time wasted. The peace of mind of traveling with the right protection has value far beyond pure financial savings.

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