Annual Multi-Trip Travel Insurance: Why We Switched to a Yearly or Long Stay Plan
If you travel more than twice a year, buying a new policy every time is costing you more than it should — here's how the annual and long-stay options work, and how to choose between them.
We never forget our mascot Mac… and our yearly travel insurance! Here in Ålesund, Norway
For years we bought travel insurance the way most people do: per trip, every time, slightly begrudgingly and always wondering if it was worth it. A policy for Iceland. A policy for Norway. Another one for Portugal. By the time we were taking five or six trips a year — which added up faster than we expected once travel became our job — without even considering the time factor.
The switch to an annual plan travel insurance felt obvious. One policy, one payment, covered for every trip we take that year — including the spontaneous ones, the long weekends, and the press trips we sometimes get a short notice for.
But an annual multi-trip travel insurance isn't the right answer for everyone. If you're planning one long continuous trip — a three-month slow travel stint through Southeast Asia, a working season abroad, a sabbatical — a long-stay policy is a completely different product and usually a better fit. Here's how both work, and how to figure out which one applies to you.
At a glance
| Per-trip | Annual multi-trip | Long-stay | |
|---|---|---|---|
| Best for | 1–2 trips/year | 3+ trips/year | One long continuous trip |
| How it works | One policy per trip | Covers all trips in 12 months | Covers one trip up to 90 days |
| Renewable | No | Annually | Yes — extends continuously |
| Cost per day | Highest | Lower the more you travel | Competitive for long periods |
| Returns home between trips | N/A | Yes | No |
🛡️ Already know which insurance plan you need? We use and recommend Heymondo for both annual and long-stay policies — it covers adventure activities, the claims app actually works, and you get a 5–15% discount* through our link. → Get the Heymondo annual multi-trip plan · Get the Heymondo long-stay plan
Annual Multi-trip Travel Insurance
If you like to hike on glaciers like us (and Mac), travel insurance is always a good idea (here in Iceland).
An annual multi-trip policy — also called yearly travel insurance — covers every trip you take within a 12-month period under a single policy. You pay once, and whether you're going to Iceland for a week in February or taking a long weekend in the Algarve in September, you're already covered before you even start packing.
The maths tips in favour of annual pretty quickly. If you're taking three or more trips a year, the per-trip cost of individual policies usually exceeds what you'd pay for a yearly plan — and that's before you factor in the time spent buying them. We've calculated our own numbers multiple times and the annual plan wins every year, but you can get a quick quote on Heymondo website to see if the maths work for you.
The key thing to understand: annual multi-trip is designed for people who travel regularly but return home between trips. Each individual trip is covered (usually up to 60 days per trip, depending on the policy), but the policy assumes you have a home base you come back to.
This is the plan we use. We're based in Spain, we travel constantly for work and pleasure — Norway for the northern lights, Greenland, Portugal up and down, Swedish Lapland, Svalbard, the US (where a simple medical visit can be very, very expensive) — and having continuous coverage means we never have a gap and never have to think about it.
Long-Stay Travel Insurance
When we stayed in the Lofoten for an extended period of time, the travel insurance for long stay was perfect
Long-stay is a different product for a different situation. If you're leaving home for an extended period without coming back — a three-month trip through South America, a working season somewhere, a longer slow travel stint — an annual multi-trip policy isn't designed for that. Long-stay is.
The Heymondo long-stay plan covers one continuous trip of up to 90 days, and crucially it's renewable — so if you're going for longer, you can extend it without starting a new policy from scratch. It's designed for people who are abroad for months at a time, not weeks.
This is also the more natural fit for people doing a working season or testing out life in a new country before committing. You get proper coverage without the assumption that you're going home in a few weeks.
Penguin Trampoline tip:
The easiest way to choose between the two: ask yourself whether you're going away and coming back, or going away and staying away. If you're leaving home for three months straight, that's long-stay. If you're taking a week here, two weeks there, and sleeping in your own bed in between, that's annual multi-trip.
Why we use Heymondo for both
We had a snowmobile accident in Svalbard — Heymondo to the rescue!
We've written a full breakdown of what Heymondo covers, how the claims process works, and how it compares to SafetyWing and World Nomads in our Heymondo review. The short version: it covers the activities we actually do (hiking, snowshoeing, snowmobiling, kayaking, or just running like a crazy person when the northern lights appear), the app works, and when something went wrong in Svalbard — a snowmobile accident on a guided tour — the coverage was there.
We've been using Heymondo for the better part of two decades — long before we had a travel blog, long before affiliate links were a thing in our world. When we launched Penguin Trampoline and started thinking about partnerships, it was a short conversation. Yes, we earn a commission when you buy through our link. But we would never recommend something we don’t actually use and enjoy. And you get a discount too! (5% year-round, 15% during special campaigns).
If you want to understand the discount structure and exactly how much you can save, we also have a guide to saving on your travel insurance with the full breakdown.
Did you know?
The Heymondo app lets you start a medical consultation directly from your phone — wherever you are. This option is especially practical if you like to explore remote destinations and follow Penguin Trampoline’s off-the-beaten-path travel guides. It's one of the most practically useful features of the policy and one most people don't know about until they need it.
Pic: Between hot springs and slippery paths (and volcanoes, the works), Jake was happy he had travel insurance in Iceland.
FAQ: Annual and multi-trip travel insurance
What is annual multi-trip travel insurance?
A single policy that covers every trip you take within a 12-month period, instead of buying a new policy for each trip. It's typically cheaper than buying individual policies if you travel three or more times a year, and it removes the hassle of purchasing coverage every time you book a flight.
What is long-stay travel insurance?
Coverage designed for one continuous trip lasting weeks or months — typically up to 90 days, with the option to renew. It's suited to slow travellers, people doing working seasons abroad, or anyone who won't be returning home between trips.
How do I know if annual or long-stay is better for me?
Annual multi-trip if you travel regularly but always come home between trips. Long-stay if you're leaving for an extended period without returning. If you're a digital nomad who moves continuously without a home base, long-stay (renewable) is almost always the better fit.
Does annual travel insurance cover adventure activities?
Depends on the policy. The Heymondo annual plan covers a wide range of outdoor and adventure activities including hiking, cycling, surfing, skiing, and more. High-altitude trekking and extreme sports may require an add-on.
How much does annual travel insurance cost?
It varies by age, nationality, and plan. The consistent finding: if you're taking three or more trips a year, the annual plan almost always works out cheaper per day than buying individual policies. You can get an instant quote through our link with an automatic 5–15% discount applied.
The per-trip model made sense when we were taking one or two holidays a year. Once travel became a bigger part of our lives, the annual plan was simply the rational choice — financially and logistically. If you're at that tipping point, run the numbers. They almost always point the same way. And it’s even better when you get a 5%-15% on top of it!
Want to be the first to know about Heymondo special campaigns — including the ones where you can get up to 15% off? Sign up to our newsletter below.
Do you love travel savings? Check out our guides:
🧭 Save on Your Travel Insurance — How we do it
🌍 Heymondo Review — Our personal experience
💸 How to Travel Cheaper — Stretch your budget, not your comfort zone.
🛫 How to Find Cheap Flights — Real tools, real tricks, no shady “hacks.”
🏨 How to Find Cheap Accommodation — Smart planning, local finds, and better value everywhere.
💰 Travel Discounts & Deals — Our favorite platforms and exclusive travel partner offers.
*Discount applicable to penguins from all countries except the US, due to legal restrictions.
