The best annual travel insurance: Options & why to choose them

Whether you travel for business, leisure, or as a digital nomad, frequent travel gives you the freedom to explore new destinations and cultures. However, it also increases the chance of unexpected problems like lost luggage, flight cancellations, illness, accidents, or needing medical repatriation. That is why today we want to talk about the importance of annual travel insurance.

It’s definitely the best option for people who travel several times a year, instead of taking out a separate policy for each trip. In this guide, we explain what annual travel insurance is, what it covers, and which the five best companies are. We’ll help you choose the insurance that fits your needs, so you won’t have to keep looking for a new policy every time you pack your bags.

What is annual travel insurance?

Annual travel insurance, also known as multi-trip insurance, is a policy that covers all the trips you take within a single year, up to a set limit. Instead of buying a separate policy every time you travel, you pay one annual premium and stay covered for all your trips throughout that period.

How does it work? Once you get the policy, it’s valid for 12 months, so if you travel several times during that year, each trip is covered. It’s more convenient than buying separate insurance for every trip, usually cheaper, and involves less paperwork. Still, you should check details like how long each trip can last, where you’re covered, medical limits, and any illness exclusions. We’ve compared it with a standard policy in the table below.

Annual travel insurance coverage

Coverage for annual travel insurance can vary by company, but most of these policies are made for travelers with specific needs. Before you buy, check that it includes the protections that matter most for your type of trips. The most common ones are:

• Medical care: Doctor visits, emergency care, medication, diagnostic tests, and specialist treatment, usually with coverage limits of several hundred thousand dollars or euros.
• Hospitalization and surgery: Hospital expenses, admission fees, intensive care, surgeries, ambulance services, and follow-up treatments.
• Medical repatriation: Medical transportation, medical escort, logistical coordination, and early return for medical reasons.
• Civil liability: Damage to accommodations, accidents involving other people, and property damage during the trip.
• Luggage: Theft, loss, damage, or delays in delivery.
• Trip cancellation: Interruption or cancellation of the trip due to illness, accident, death of a family member, or work-related emergency.
• Adventure sports: Coverage for activities such as hiking, surfing, scuba diving, snowboarding, skiing, and rafting.
• 24/7 assistance: Telephone assistance in your language for medical care, translation, emergencies, or legal advice.
• Optional coverage: You can extend your coverage to include electronic devices, rental cars, legal expenses, or accompanying family members.

When should you purchase annual travel insurance?

Annual travel insurance isn’t for everyone, but it can be a good option if you travel several times a year and don’t want to buy a new policy for each trip. It’s especially useful if you travel more than three times a year, take regular weekend trips, or often travel for work. The more you travel, the more likely it is to be cheaper than buying separate insurance every time.

More and more people can work remotely and choose where they live and travel, which is why digital nomads often use annual travel insurance. If that’s your case, check the maximum length allowed per trip, since some policies only cover stays of 30, 60, or 90 days in a row. Annual insurance can also be worth it if you don’t travel often but go to countries where healthcare is very expensive, like the United States, Canada, Japan, or Australia.

Many people prefer not to deal with finding travel insurance every time they fly, so if you tend to travel spontaneously without much planning, this type of policy gives you more peace of mind and convenience.

The 5 best annual travel insurance plans in 2026

To choose between the different annual travel insurance options on the market, it’s important to look at the key details a policy includes. The main ones are medical coverage, maximum trip length, support in your language, luggage protection, and overall price and value. It’s also helpful to read reviews from other users on platforms like Trustpilot. Below, we look at some of the best travel insurance options for 2026.

1. IATI Annual Multi-Trip

IATI is one of the most popular travel insurance companies and offers several specific plans, including its Annual Multi-Trip policy, which has become one of the industry’s main reference points. This policy allows you to take multiple trips over the course of a year, with stays of up to 90 days, or 6 to 12 months with the higher-priced “Great Travelers” option. These are the main benefits it includes:

• Medical coverage: $349,245.
• Trip cancellation: Optional up to $2,300.
• Luggage: Up to $1,395 for damage, loss, or theft
• Repatriation: 100% covered.
• Adventure sports: Accidents covered, and up to $3,490 for search and rescue.
• Emergencies: Advance payment of up to $3,490.
• Accidents: Up to $17,460 for disability or death.
• Price: Starting at $250 per year for short trips and $1,250 for long stays.

2. Heymondo Annual Multi-Trip

Another digital insurer that offers annual travel insurance is Heymondo, with a policy that covers trips of up to 90 consecutive days, although it also has an option for longer stays. In addition to the standard coverage, you can add extra options to customize the policy to your needs.

• Medical coverage: $3,495.
• Trip cancellation: Optional, covering 42 reasons for cancellation.
• Luggage: Up to $2,910 per incident of damage, loss, or theft.
• Repatriation: 100% covered.
• Adventure sports: Included, with the option to add more sports.
• Emergencies: Included with advance payment.
• Accidents: Up to $29,100 for disability or death.
• Price: Starting at $350 per year for short trips and $320 for the first 90 days of long stays.

3. Allianz Annual Multi-Trip

If your trips are under 60 days, you can get Allianz annual multi-trip insurance with two options: Silver Assistance or Gold Assistance with Cancellation, which includes more coverage. You must buy it before your trip starts to be covered. Allianz is one of the most experienced insurance companies on the market, with over 60 years in the industry. These are the benefits it offers:

• Medical coverage: $349,240.
• Trip cancellation: Up to $2,330.
• Luggage: Up to $1,785 per incident of damage, loss, or theft.
• Repatriation: 100% covered.
• Adventure sports: Not included.
• Emergencies: Included, with search and rescue.
• Accidents: Up to $5,830 for disability or death.
• Price: Starting at $0.38 per day with the Silver plan and $0.52 with the Gold plan.

4. Chapka Cap Annual Multi-Trip

Chapka is another popular choice, especially among backpackers and frequent travelers. The policy covers trips of up to 90 days anywhere in the world. There’s also a family discount, and it includes the following coverage:

• Medical coverage: $582,955.
• Trip cancellation: Up to $1,750.
• Luggage: Up to $2,915 per incident of damage, loss, or theft.
• Repatriation: 100% covered.
• Adventure sports: Included at no additional cost.
• Emergencies: 100% of expenses.
• Accidents: Up to $34,980 for disability or death.
• Price: Starting at $380 per year for an individual or $965 for a family of three to five members.

5. AXA Multi-Trip

Finally, we wrap up this overview with AXA. If you travel more than twice a year and your trips are under 60 days, you can choose between two plans depending on whether you travel within Europe or elsewhere. You also get two days of free mobile data (up to 1 GB) in your destination with a free eSIM. Here are its main benefits:

• Medical coverage: $1,750.
• Trip cancellation: Optional.
• Luggage: Up to $1,750 per incident of damage, loss, or theft.
• Repatriation: 100% covered.
• Adventure sports: Not included.
• Emergencies: 100% of expenses.
• Accidents: Up to $58,295 for disability or death.
• Price: Starting at $100 for trips within Europe or $190 for worldwide travel.

How to stay connected to the internet while traveling

Another way to stay safe when traveling abroad, besides annual travel insurance, is to have a stable and secure internet connection. This lets you manage bookings, use GPS, make video calls, or work remotely without interruptions or relying on public Wi-Fi. It also helps you contact your insurer in an emergency, find hospitals, and stay connected throughout your trip for peace of mind.

If you need an eSIM that works anywhere, Holafly’s monthly plans are a good option, with unlimited data in over 160 destinations at one price. You can choose a 25 GB plan or unlimited data, and use it on multiple devices at the same time. If you’re only traveling short-term, you can also get Holafly’s international eSIM with unlimited data just for the days you need.

Frequently asked questions about the best annual travel insurance plans

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Paula Henderson

Spanish-English Translator

Hi! I'm a Spanish-English translator working with Holafly, helping bring travel content to life for curious travelers. As a digital nomad with a passion for exploring, I'm always adding new spots to my bucket list. If you love to travel like me, stick around because you're in the right place to find inspiration for your next trip! ✈️🌍

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