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Travel insurance for sabbaticals and longer trips

Travel insurance is one of those trip essentials I recommend to other travellers. I’ve written about it several times before, most notably on why I always buy travel insurance and whether travel insurance is worth it, and it was definitely a consideration when planning for my own career break. If you are looking to buy travel insurance for sabbaticals and longer trips that cover many different countries, you do have to pay attention to the fine print to make sure you are properly covered – I only realised halfway through my travels that my annual travel insurance plan wasn’t sufficient cover so I had to scramble for some last-minute options.

In this post I’ll tell you a little more about my experience and expenses, and look for some other travel insurance options for sabbaticals that you can consider as well for your own needs – namely SafetyWing and World Nomads.

This post is sponsored by SafetyWing. Some of the links in this article are affiliate links, which means I may get a small % of any sales made through that link, but it has no impact on your own costs.

Travel insurance for sabbaticals – my experience

The one thing I’ve found about travel insurance that you can’t get around is that there really isn’t a one best solution in terms of price and coverage for everyone. I wish there was because I’m quite lazy and by golly reading fine print is not my idea of fun, but the right travel insurance plan is pretty dependent on your individual circumstances so if you want to save money, put in the research. I thought I’d help you out a little and break down my own career break travel insurance considerations for you.

Bucharest Chimopar Me Walking Grass
Just a random shot of me in Bucharest during my career break taken by friend Annemarie from Travel On The Brain

I took my career break from late March 2016 to early June 2017 over a total period of about 15 months – you can read more about my career break experience here where I detail how I planned and executed the trip. I had an overview about my travel insurance costs in that article, but here’s a more detailed breakdown for you, and I’ll go into more details about why I did what I did below:

GE Annual travel insurance plan (365 days: March 2016 – March 2017)S$468
GE Annual plan renewal (365 days: March 2017 – March 2018)S$398
Additional World Nomads plan [affiliate link] (69 days: late March to early June 2017)S$392
AVERAGE COST PER DAY (Over 2 years) S$1.73

Annual travel insurance plans

S$468 + S$398 = S$866

I buy annual travel insurance plans for my travels on a normal basis because I think I do travel enough to make up the cost, and also I got tired of remembering to buy a plan last-minute because I forgot or it’s a last minute trip that tends to happen because blog trips can be quite short-notice. I usually buy my travel insurance through my agent from GE because he’s a friend and also sorts out all my insurance paperwork for me.

I didn’t think it would be an issue for my sabbatical until I had to make claims for my stolen phone in Budapest and my doctors’ visits and medicine was covered when I lost my voice in Poland. When checking in with my insurance agent on whether the loss would be covered, we realised that there actually a 90-day trip limit for my annual plan – i.e. while I was covered for the entire year, each trip that I took could only be 90 days maximum before I had to return to Singapore in 90 days to ‘reset’ my insurance coverage. Luckily the incident took place within that 90-day period so I did get my payout.

A note here that while my career break technically lasted 166 days over about 15 months, my two annual plans did cover a longer period of 24 months (two years) and 10 other trips that I took from July 2017 to March 2018.

Budapest Parliament House River Grey Day
One of the first pix I took with my newly bought phone in Budapest. I can’t show you any pix of the baths obviously because they were lost with the stolen phone!

Additional nomadic insurance


Now that I knew I needed additional coverage beyond the 90-day limit, I decided to purchase additional weeks coverage from World Nomads [affiliate link] when my South America leg stretched beyond 3 months. I ended up buying 69 additional days (about 10 weeks worth) of insurance cover till I returned to Singapore in June 2017. Luckily during this period I did not need to make any claims, but having the cover was reassuring and I needed to have coverage for more extreme activities like cycling the Death Road.

I found the World Nomads sign up pretty easy to do on the road because I could do everything online while on the road. Also, it was easy to extend on the go as my return day was pushed back, but you can also see that the cost of this add-on plan was pretty pricey – my 69-day plan was equivalent to my annual 365-day plan, and while it’s not exactly comparing apples to apples since the plans are different, it’s a concern cost-wise nonetheless.

Bolivia Death Road Cliff Me
Yeah you need travel insurance to cycle the Death Road

Thoughts on hindsight

In total I spent S$1,258 on travel insurance coverage over 2 years – that works out to about S$629 for 1 year or about S$1.73 per day over 2 years. It’s not a lot in the grand scheme of things if you consider on a per-day basis, but it’s not a small sum to for someone to spend either. I think I might have been able to save more if I had planned better – let’s put that to the test.

Sabbatical travel insurance options

Insurance comparison tools

Travel insurance is pretty easy to buy these days – you can find many providers and get quotes online. If you don’t go through an agent like I do and prefer to DIY, you can also use comparison sites to do a quick comparison of benefits and features, but always take the time to look at the fine print before you purchase.

A caveat: I’ve not used all these sites much myself because my agent does most of the work for me, but I did use them a little in researching this article and I thought they were pretty good. If you have your favourites, tell me about them.

Single trip vs Annual trip cover

One option I could have considered instead of getting an annual plan was to go for a single-trip plan instead. Most annual plans tend to have a 90-day/trip travel limit, but there are single-trip plans that can cover for up to 180 days/trip, which could have worked for me because my longest stretch ended up being 166 days (about 5.5 months).

Some people I know will actually fly back to Singapore at the end of 90 days to ‘reset’ the insurance. That would have worked if I had been in a nearer region where I could get a cheap/short flight, but in my case I was in Europe or South America at the 90-day mark of my travels, so having to take all that time and money just to fly back didn’t seem to make sense to me.

Peru Machu Picchu Sungate View Me
In Machu Picchu somewhere around Month 4 of my travels – I definitely wasn’t going to be flying back home just yet. I even had to sell my Coldplay concert tix because I realised I wasn’t headed home just yet

That said, while single-trip travel insurance can cover for up to 180 days, it starts to get quite expensive once you extend your trip over a month. I did a check on prices for just my South American leg that lasted 166 days/5.5 months on the comparison sites and found quotes ranging anywhere from $550-$1,200+. Some companies were running promotions that dropped prices to $300-$700, but you have to hope that promotions are being run when you need them.

Ultimately it does depend on how long you plan to travel for – I wouldn’t have had any issues if my travel legs had been within the 90-day limit. But if you are looking to be on the road at a go for longer periods without returning home beyond 180 days, single-trip plans might not be the answer either. I knew how long my Europe leg was but I had no idea how long when I would finish my South America journey, so it would have put a bit of a damper on spontaneity.

Nomadic insurance option: SafetyWing

Most insurers usually require you to start and end the trip from your home country (in my case Singapore), but nomadic travel insurance providers don’t require you to have a specific start point, so it was ideal for me to use as an extension of my existing plan. Back in 2017 I used World Nomads [affiliate link] but there wasn’t really any other option then.

The whole reason I decided to look into this more was because the SafetyWing [affiliate link] folks got in touch to introduce their travel medical insurance at a rate of US$37/4 weeks. SafetyWing is underwritten by Tokio Marine, a pretty well-known MNC insurance company headquartered in Japan, but they have a bright and cheery website that stands out from your more typical staid insurance companies and they position themselves as insurance by digital nomads for digital nomads – i.e. those who work on the go and don’t have a fixed homebase or go home all the time.

You don’t need to know your end date, ideal when you don’t have a return flight booked, and if you’re forgetful like I am, the auto-renewal feature means you won’t end up forgetting to buy a plan and be left uncovered because your previous plan expired.

Most travel insurance only covers you when you are away from home, but SafetyWing includes home country coverage, meaning that you are insured for up to 30 days for every 90 days of coverage in your home country – ideal for the digital nomad who doesn’t already have their own insurance plan in the event you swing home for a visit, emergency or visa run.

For those with families, you can also include your young children in the plan without extra cost – that’s 1 young child (14 days to 10 years old) per adult, and up to 2 per family, age between 14 days and 10 years old.


SafetyWing only started in 2018, but if this had been around in 2017, I would have saved quite a lot more because for the same extension of 69 days, it would only have cost me US$92.40/S$126 – that’s less than half of what I paid for my WorldNomads extension (US$288.58/S$392).

Check out SafetyWing insurance [affiliate link] insurance here

A note of course that while price is one major factor to consider, what you’re actually covered for is another big consideration. There’s no point paying for the cheapest option only to realise that you can’t make any claims when you actually get in trouble. We’ll talk a little more about that below.

Comparing sabbatical insurance in 2020

Price comparison

I thought I’d do a side by side comparison of all these other options available now to see whether it could have saved me money if I had done my due diligence for my own sabbatical. What you’re seeing here are rough estimates based on how I travelled back in 2016-2017.

My trip can be broken down into a few portions as I wasn’t travelling continuously through the 15 months. I guess my travels might not be the most conventional because beyond my long stretches travelling, I also had smaller trips in between for the travel blog.

Career Break 2016-2017 Flight Map
Tracing my flight paths in 2016 and 2017
  • Part 1: Japan-Taiwan (57 days)
  • Part 2: San Francisco (4 days)
  • Part 3: Europe-Kenya (113 days)
  • Part 4: Indonesia-Philippines-Laos-Thailand (4 trips, 9+8+6+5 days = 28 days)
  • Part 5: South Korea-Canada-South America-Europe (166 days)

I’m going to pre-emptively apologise if I make any errors in the calculations because I tried my best but too many numbers boggle me, but I used the various calculators and the prevailing google exchange rate as of Dec 2019 to make these estimates. You are welcome to point out any errors that I will happily fix but please do it nicely.

GE Single Trip Plans

Part 1: 56 days – S$299

Part 2: 4 days (USA) – S$42

Part 3: 113 days – S$596

Part 4: 28 days (4 trips) – S$338

Part 5: 166 days – S$827

Grand total: S$2,102

Prices quoted here are for GE TravelSmart Premier Elite tier which is what I was using for my own career break. There are prices for 1-28 days and $33/week for additional weeks after based on the brochure

World Nomads

Part 1: 56 days – S$357 (US$264.50)

Part 2: 4 days (USA) – S$60 (US$44.50)

Part 3: 113 days – S$701 (US$519.50)

Part 4: 28 days (4 trips) – S$321 (US$241)

Part 5: 166 days – S$935 (US$692.50)

Grand total: S$2,378 (US$1,762)

Prices quoted here are from the higher tier Explorer plan via the WorldNomads calculator on the website


Part 1: 56 days – S$99.77 (US$73.92)

Part 2: 4 days (USA) – S$16.33 (US$12.10)

Part 3: 113 days – S$181.72 (US$134.64)

Part 4: 28 days (4 trips) – S$49.88 (US$36.96)

Part 5: 166 days – S$ 296.80(US$219.92)

Grand total: S$744.31 (US$551.46)

Prices quoted here are via the SafetyWing calculator on the website

Holy cow, SafetyWing definitely is a lot cheaper than any of the other two options. The GE and WorldNomads plans are about on par – an annual plan really makes more sense if you are planning to take anything more than 3-4 weeks worth of travel in total.

Coverage comparison

So here’s the other important thing – let’s take a closer look at the type of coverage you will be getting. I’m not going to compare every single detail because that’s just way too much work, but I thought I’d look at some of what I think are important things to be covered for because they tend to happen to travellers (more accurately, me).

Again, this is just an overall summary, please don’t take this as the holy grail. Take the time to read the most updated policy wording and schedule of benefits to ensure that whatever you need to be covered is covered sufficiently.

GE TravelSmart (Elite Plan)World Nomads (Explorer Tier)SafetyWing
Overall Max LimitS$1,000,000UnlimitedUS$250,000 (S$336,473)
Travel DelayS$100 every 6 hours (max S$1,200)US$1,000 (S$1,346) over 12 hours Up to US$100(S$135)/day after 12-hour delay req. overnight stay (max 2 days)
Lost PropertyS$500/item, S$1,000 for laptop, S$5,000 maxUS$500 (S$673)/item, US$725 (S$976)/electronic item, US$3,500 (S$4,711) max Checked luggage only: US$500 (S$4,711)/item, US$3,000 (S$4,038) max
Maximum per Injury/IllnessS$500,000UnlimitedUS$250,000 (S$336,473)
Emergency Medical EvacuationS$1,000,000US$500,000Up to US$100,000 (S$134,589) lifetime max
Sports and ActivitiesScuba diving, bungee jumping, skydiving, skiing, paragliding, parasailing, mountaineering <3,000mMost major commercial sporting and extreme activities are covered, like scuba diving, bungee jumping, skydiving, skiing, mountain biking. Full list here.NOT COVERED: ATV, paragliding, parasailing, white water rafting, luge, racing, mountaineering >4,500m
Policy WordingTravelSmartWorld NomadsSafetyWing

You might save costs with SafetyWing, but looking at the coverage, it does seem like it covers less things and pays out lower amounts overall at a quick glance. This is when you seriously need to consider what your needs are and how important certain coverage is to you. There isn’t really a right answer to this, but it’s how much you are comfortable with paying for and being covered.

From what I can see, SafetyWing might not be great if you plan to do lots of activities as it doesn’t provide as much cover as World nomads – some of the things I did on my trip like going parasailing or white water rafting in Panama would not have been covered. But if you still want some cover without having to pay so much, it looks like a decent option for everyday cover, but I was also surprised to see that they only covered checked baggage loss and not for general stolen items (which unfortunately has happened to me several times).

In conclusion

If I had to do my career break / sabbatical trip all again, would I still go with the same travel insurance options as I did before? Based on how I travelled, I think I still would opt for an annual plan but I might consider using either World Nomads or SafetyWing to extend beyond the 90-day limit, depending on what I think I would be doing in that additional period. I’m not currently using GE anymore because after the claims, they raised my premiums so I switched to a different provider.

I do like that SafetyWing is so much more affordable and flexible, but I’m also concerned that the cover may not be as comprehensive as what my current travel insurance provides based on my needs, which is why it’s important to read the policy wording carefully to know exactly what you’re covered for.

This post is sponsored by SafetyWing. The SafetyWing links in this article are affiliate links, which means I may get a small % of any sales made through that link, but it has no impact on your own costs.


Monday 27th of January 2020

this is so great, cause u give some information about travel insurance for sabbatical.. i think this posting can have some education and about money to travel