OMAAT reader James asked if I’ve ever written about my approach to travel insurance. As he asked, “not sure if you ever buy it sporadically or have an annual policy, but you’ve been to some pretty far flung places, and I’m curious how you protect yourself and your family when you travel.”
Well, I don’t think I’ve ever addressed this in a post before, but I have a confession to make… and I hope to learn something from the comments section of this post!
In this post:
I don’t typically buy any sort of travel insurance
I don’t think I’ve ever deliberately purchased travel insurance, believe it or not. Maybe I take too much of an “out of sight, out of mind” approach to this. I can’t say I’m familiar with travel insurance policies in great detail, though generally speaking, I tend to think they fall into one of several categories (with a huge amount of variability, of course):
- There’s the type of travel coverage you may get with credit cards, for things like rental car coverage, lost luggage, delayed flights, emergency evacuation, etc.
- There’s more health insurance focused coverage, for any sort of illness or hospitalization that may happen abroad
- There’s travel insurance that covers things like trip cancelation due to illness, or some policies even allow travelers to cancel their trip for any reason, and receive reimbursement
Typically, my approach has been that I try to strategically use credit cards that offer certain types of travel coverage, for rental cars, delayed bags, emergency evacuation, etc. Beyond that, though, I haven’t really purchased coverage. Why?
- Since I often use airline and hotel points for my travels, that gets complicated in terms of potential reimbursement with these policies, and it also gives me more flexibility, since these kinds of reservations can often be canceled until close to departure
- While the concept of a “cancel anytime” travel insurance policy sounds great, they’re typically astronomically priced for obvious reasons
- So my only concern would be for some sort of a health emergency outside the United States, though frankly healthcare is usually so much more reasonably priced abroad, so it’s not something I put much thought into
- I generally find insurance to be a hassle, given the terms, conditions, restrictions, etc.
I tend to think that insurance policies are important for things you couldn’t reasonably afford to fund or replace, like major damage to a home, treatment for a long term illness, etc. But when it comes to things that could reasonably come up when traveling abroad, I think that I’m lucky enough to have a safety net where it’s not worth spending extra money to be protected in that way.
Similarly, I can understand wanting travel insurance if you’re planning a once in a lifetime trip, or something, but for me, travel is a pretty consistent part of life.
How do other frequent travelers approach travel coverage?
The above is the approach I take, but that’s not to say that it’s the correct approach. If anything, perhaps my luck with traveling so far has made me not consider this, when it’s something I should put more thought into, especially with an increasing amount of family travel. Perhaps I’m just in the “ignorance is bliss” camp.
So I’d love to learn from others. What approach do you take with travel insurance policies? Is there some sort of annual policy that makes sense, especially for those of us who frequently redeem points, and as a supplement to the coverage we have on many credit cards? Or are there per-trip policies that it makes sense to purchase?
Bottom line
I love when I’m asked questions I simply don’t have answers to, because it gives me an opportunity to learn. While travel insurance is a massive industry, it’s one that I’ve not put much thought into. I hope that the limited coverage provided by my credit card will provide some value, but other than that, I’ve never really purchased a policy.
To fellow frequent travelers, where do you stand on the concept of travel insurance? And to those who use it, how do you do the math on it?
Mixed bag to be honest. I got severely hosed during COVID for our honeymoon/bucket list to the Maldives. We had travel insurance, but somewhere along the line, New York state prohibited CFAR policies. So when the foreign quarantines came into play, I contacted the Berkshire Hathaway policy reps and they pointed out that "government regulations" were an exclusion. So even though you couldn't travel (the resorts WERE open), no coverage. We had to pre-emptively cancel...
Mixed bag to be honest. I got severely hosed during COVID for our honeymoon/bucket list to the Maldives. We had travel insurance, but somewhere along the line, New York state prohibited CFAR policies. So when the foreign quarantines came into play, I contacted the Berkshire Hathaway policy reps and they pointed out that "government regulations" were an exclusion. So even though you couldn't travel (the resorts WERE open), no coverage. We had to pre-emptively cancel as the resorts had an escalation cancellation policy (ie: cancel 60 days out, lose 25%, cancel 45 days out, lose 50%, etc.) End result: Lost about $10,000. One resort did offer to "hold" our money and let us rebook for the next year, but COVID was "still a thing" a year later, and they did graciously refund the money.
Have had to use the other policies occasionally (health issues, etc.) Even when traveling to Hawaii, only one doctor was "in network' with my PPO and it was on another island. So rather than spend the money to fly, etc. went "local" and did get reimbursed by the travel insurance. (note that the PPO only covers EMERGENCY ROOM visits, not "urgent care" if out of network). If I'm just flying to visit relatives I may or may not. Credit cards dont' always cover you (a few are now requiring that you charge 100% to that card), or their coverages are long (ie: travel delay of 8 or 12 hours vs. 4 hours on some policies), etc.
Ultimately it comes down to risk tolerance and how much you can "afford" to be out at the end of the day. If you're OK having to take a flight 2 days later and pay for your own hotel/meals due to weather (out of airlines control, etc.) then no need for insurance.
I buy 30 day plans 12 times a year. About 25-50$ a month. Pays for delays, emergency medical and medical evacuation. It's relatively easy to use and especially for those on High Deductible health insurance policy can save thousands
I pay ~$120 for annual medical coverage. $250 deductible and $500k coverage. There's limits on how many days out abroad etc but it's not for routine stuff but in case I break my ankle, it's covered.
Health care may be cheaper abroad for the people who live there, but that's not necessarily the case for visiting foreigners. If a US citizen was to be hospitalised in Australia, for instance, they would rack up a substantial bill. One must also consider the cost of an international medical transfer if required - it's very expensive to transport you on a stretcher and accompanied by doctors and RNs to the other side of the...
Health care may be cheaper abroad for the people who live there, but that's not necessarily the case for visiting foreigners. If a US citizen was to be hospitalised in Australia, for instance, they would rack up a substantial bill. One must also consider the cost of an international medical transfer if required - it's very expensive to transport you on a stretcher and accompanied by doctors and RNs to the other side of the world. We never skip the insurance - there are too many horror stories of people being left with $1M+ bills for ICU care followed by an air ambulance home. Even if you're very wealthy, that's money you could better spend elsewhere. Buy the insurance.
“my oldest brother . . . died in an accident at a young age.”
So, that’s your plan to avoid serious illness in a faraway place? Die quickly? For someone closer to 40 than 29, who makes his living "on the road," it’s irresponsible parenthood to travel uninsured for catastrophic healthcare events.
My primary health insurance covers me internationally, out of network of course... so between that and CSR I feel pretty covered health wise.
I don't buy any sort of travel insurance ever, other than what is offered by CSR/AP. Insurance companies are there to make money, so statistically they make profit by over-insuring people. I only buy insurance for anything that I couldn't afford to just replace myself, so basically I only insure health, home...
My primary health insurance covers me internationally, out of network of course... so between that and CSR I feel pretty covered health wise.
I don't buy any sort of travel insurance ever, other than what is offered by CSR/AP. Insurance companies are there to make money, so statistically they make profit by over-insuring people. I only buy insurance for anything that I couldn't afford to just replace myself, so basically I only insure health, home and auto in my life. Even those with really big deductibles to keep the mandatory monthly premiums as low as possible. I'm on the risk side of the moral hazard equation.
Don't forget that quite a few countries stipulate travel insurance as a condition of entry. Not needing a visa to visit a country doesn't mean that you have an unfettered right to turn up and get in as you please and, much like the requirement for onward tickets, having been stamped in with a smile and no questions asked on multiple times is no guarantee that you won't be turned straight back on your next...
Don't forget that quite a few countries stipulate travel insurance as a condition of entry. Not needing a visa to visit a country doesn't mean that you have an unfettered right to turn up and get in as you please and, much like the requirement for onward tickets, having been stamped in with a smile and no questions asked on multiple times is no guarantee that you won't be turned straight back on your next visit.
I have an annual travel insurance policy which covers medical emergencies with a reasonable excess (which means that it's not worth claiming for basic doctor visits in most parts of the world) keeping the price quite low and has a few other benefits, including the marvellous feature (which many others don't provide) of covering missed flight connections on separate tickets/airlines!
I'm kind of a "belt and suspenders" guy when it comes to insurance. Now that I'm in my 60's its more likely that things will start to happen when I least expect them. I have a Blue Cross/Blue Shield international travel health insurance plan that includes high coverage for medical evacuations. It's like $485/year but it provides a lot of piece of mind when traveling overseas. And I also have a separate policy for trip...
I'm kind of a "belt and suspenders" guy when it comes to insurance. Now that I'm in my 60's its more likely that things will start to happen when I least expect them. I have a Blue Cross/Blue Shield international travel health insurance plan that includes high coverage for medical evacuations. It's like $485/year but it provides a lot of piece of mind when traveling overseas. And I also have a separate policy for trip cancellation/interruption, lost and damaged baggage, and accidental death. Both cover unlimited trips and destinations, so I'm well-protected.
Like a few others here, I also use Allianz annual travel insurance (family plan), mainly for emergency medical evacuation and treatment. The Basic option is quite affordable and has enough of a coverage for most of the trips one may take, so it's a good option for US-based travelers. Some trips require emergency medical insurance as a condition of sale, for example, antarctic cruises and safari camps. When I went to St. Helena a couple...
Like a few others here, I also use Allianz annual travel insurance (family plan), mainly for emergency medical evacuation and treatment. The Basic option is quite affordable and has enough of a coverage for most of the trips one may take, so it's a good option for US-based travelers. Some trips require emergency medical insurance as a condition of sale, for example, antarctic cruises and safari camps. When I went to St. Helena a couple of years ago, the government mandated medvac insurance (with a minimum coverage requirement) as condition to enter. Having annual plan takes care of all of that.
Considering that my partner and I are in our mid-70s and one of us has significant health challenges, our approach to travel insurance revolves almost exclusively around medical (and medical evacuation) coverage. For several years we've bought an annual Trekker Choice policy from Blue Cross Blue Shield Global Solutions that covers virtually all medical costs incurred outside the United States. No pre-existing conditions. Last annual premium was $483 for two people. The only requirement is...
Considering that my partner and I are in our mid-70s and one of us has significant health challenges, our approach to travel insurance revolves almost exclusively around medical (and medical evacuation) coverage. For several years we've bought an annual Trekker Choice policy from Blue Cross Blue Shield Global Solutions that covers virtually all medical costs incurred outside the United States. No pre-existing conditions. Last annual premium was $483 for two people. The only requirement is that you have a US-based primary care health insurance policy (Medicare included). Last used this summer during a Seabourn Alaska cruise while in a Canadian port. My partner fell and broke/lacerated his left arm. Initial care and follow up was provided onboard the ship, and the total cost of USD $600+ was charged to our cruise folio. Once home we were reimbursed the full amount minus a USD 100 deductible. So, for us this kind of medical insurance coverage provides a huge safety net.
I mean a normal travel insurance is probably not needed, because you can always financially sustain the loss of a trip you booked but were not able to take.
But everyone should In my opinion have a medical coverage for trips as these costs cannot be foreseen and are unpredictable and can go far beyond your trip cost.
Always get medical insurance. Annual policy. Have had to claim twice. Once getting covid whilst on a tour, had to leave the tour. Once when phone was pickpocketed in Bangkok. Travel regularly to the States. Would not wing it there without medical insurance cover with the off the charts cost of healthcare there.
Not travelling with travel insurance is trying to save money in the wrong place. Those credit card coverages have too many...
Always get medical insurance. Annual policy. Have had to claim twice. Once getting covid whilst on a tour, had to leave the tour. Once when phone was pickpocketed in Bangkok. Travel regularly to the States. Would not wing it there without medical insurance cover with the off the charts cost of healthcare there.
Not travelling with travel insurance is trying to save money in the wrong place. Those credit card coverages have too many ifs and buts to be of any use if you need it.
My understanding was Amex Platinum offers emergency evacuation with no limit whether or not you paid for the trip with Amex. CSR offers it with $100k limit with part of trip paid by Chase.
As for emergency medical, CSR offers $2500 if you pay for the common carrier with Chase, but I think it's really for if you get sick while you are on the common carrier itself.
Your medical insurance plan may also offer...
My understanding was Amex Platinum offers emergency evacuation with no limit whether or not you paid for the trip with Amex. CSR offers it with $100k limit with part of trip paid by Chase.
As for emergency medical, CSR offers $2500 if you pay for the common carrier with Chase, but I think it's really for if you get sick while you are on the common carrier itself.
Your medical insurance plan may also offer emergency coverage abroad (mine does and specifically excludes non-emergency coverage abroad).
As for trip cancellation, again, Amex Platinum and CSR offer coverage which may help if you, etc. are injured, yada yada yada.
I don't think coverage where you just change your mind and don't want to travel has too much value except if you are buying a tour package depending on what their refund policies are, deposits, etc. With US carriers you may (or may not) have some fees with the airfare (if you bought basic economy) but you'll get a travel credit. And unless you are buying non-refundable hotels, you'll usually be able to cancel hotel reservations without penalty (and if you are cancelling within a 24 hour window, it may be for a reason that is already covered by trip cancellation insurance).
Just my two cents.
@Lucky. Before our most recent trip, the only time I purchased travel insurance was during the pandemic when Oman required it to enter the country. A month ago I purchased travel insurance for our 2 week long trip to NZ and Fiji. I did that because we are almost at retirement age and felt that we just do not want to take chances should anything bad happen to us (health-wise). The $129 premium for a 2 week trip for two of us was worth the peace if mind for us.
Absurd question.
So many reasons why you should.
Americans believe if they are in the U.K. or EU they will get free healthcare in case of an incident. No. They are not residents and taxpayers. You pay and claim it via your insurance.
Americans buy no refundable tickets and expect the airline to bail them out.
I'm the first person to say that Britons overinsure themselves for everything, but some of the attitudes on show here really are shocking!
Ben, it's why they call you Lucky.
Since original Medicare doesn’t cover outside the US (with a few "nearby" exceptions), it is important to take that into account. My Medicare Advantage plan covers "emergency" treatments outside the US, but not "followups." So, I get an annual plan that covers all the travel medical (within policy limits) and offers evacuation.
Btw, the plan for a 65yo is only about $275/yr and has some non-medical coverage also. I'm willing and able to self insure a number of things, but I'll have house, car, medical, and this without question.
Medicare Advantage = Your screwed and you believe TV commercial
If you get a Medigap most of the plans cover emergency abroad.
You can get an annual policy for under $100. It’s a no brainer and your US Insurance will not work out of the country. I have used my plan for medical,delays and cancellations.
My US healthcare insurance covers me internationally
My insurance considers it out of network and the reimbursement is minimal. Moreover. The facility you are seeking care may demand full payment before treatment even though you may be covered. Was in Jamaica and I had to come up with over $40,000 to get my mother to the hospital and surgery. Yes it was covered when we got home but the facility in Jamaica wanted their money. My lesson on why I get travel insurance.
I have some medical concerns, but luckily haven't had anything too serious abroad. Nonetheless, I used to cover my health while traveling with the oddly named IMG insurance "Patriot" plan. Now that I have Kaiser health insurance they cover international urgent care on most plans. However, not on the Medicare Advantage plan apparently. I'm not on that plan yet, but was surprised to read that that plan excludes coverage.
We cruise once or twice a year and the insurance costs offered through the cruise lines are exorbitant. We find it's better to purchase an annual policy through Allianz that covers cancellation, medical, etc. given that our average cruise costs are $5-15k each. If it wasn't for the cruises we probably wouldn't carry the coverage, but even a minor medical event on board can easily run well over $1k. We also use CC's for things...
We cruise once or twice a year and the insurance costs offered through the cruise lines are exorbitant. We find it's better to purchase an annual policy through Allianz that covers cancellation, medical, etc. given that our average cruise costs are $5-15k each. If it wasn't for the cruises we probably wouldn't carry the coverage, but even a minor medical event on board can easily run well over $1k. We also use CC's for things like rental car coverage, trip delay, etc.
Keep in mind that medical evacuation insurance generally just pays for the patient to be transported to the nearest available qualified care facility.
So if you are an American on a Safari in Africa, you might get a plane ride to Germany, not back to America.
I travel for over 30 years a yearly average as you, even more and never ever I took any kind of insurance. For what regards healthcare insurance, the country where I live and pay covers that in any place of the world. And yes, unfortunately I have the experience.
I am based in Germany and have the following insurances:
- 9,99€/yr medical insurance
- 99,99€/yr travel comfort insurance
- 101,22€/yr rebooking for any reason insurance
The travel comfort insurance pays me a fixed sum 100€ per hour delay (reason doesn't matter, no receipts asked). This has already saved me thousands.
My rebooting insurance reimburses me fare difference and penalties should I decide to rebook a flight. If a flight is non refundable,...
I am based in Germany and have the following insurances:
- 9,99€/yr medical insurance
- 99,99€/yr travel comfort insurance
- 101,22€/yr rebooking for any reason insurance
The travel comfort insurance pays me a fixed sum 100€ per hour delay (reason doesn't matter, no receipts asked). This has already saved me thousands.
My rebooting insurance reimburses me fare difference and penalties should I decide to rebook a flight. If a flight is non refundable, they will pay the full cost of the new flight to the same destination country.
No deductibles for all these insurances.
€17 a month is great and hopefully you never need to claim, however it’s a safety net. My monthly is around the same however not so comprehensive. The main thing is medical cover
My health insurance is supposed to cover medical care overseas in an emergency, at least for the European countries and Japan when I asked.
If I were 50 and older is questionable health, 60 and older with frequent travel, or 65 and older, I would get medical evacuation coverage. If I flew to countries other than Singapore, Taiwan, Japan, Australia, NZ, UK, original 9 EEC countries, or Scandinavia, I would really think about evacuation.
I always buy medical insurance, including emergency evacuation, when traveling abroad. Although not as expensive as the USA, healthcare would still cost thousands of dollars if you end up being hospitalized most anywhere. The insurance cost depends on your age/country/length of trip and starts in the $20-$40 range.
I only buy insurance for perils that might bankrupt or severely pinch. Medical and evacuation coverage are not adequately covered by any credit card unless it’s a modest issue. An annual policy from GeoBlue fits this gap. The handle direct bill from many hospitals or out of pocke too.
Chase Visa for routine travel. Extra insurance for bucket trips like Antarctica. Nomads for Alps and such.
I start by charging everything on my CSR. Yes, I've read both good and bad stories about the coverage, but it's a start. For more exotic trips I buy Medjet evacuation, such as when we went on safari in Zambia and Botswana.
Ben, the cancel for any reason is less for when you get sick, but when your child does. We don't have children, but when my mother-in-law was in assisted living after a...
I start by charging everything on my CSR. Yes, I've read both good and bad stories about the coverage, but it's a start. For more exotic trips I buy Medjet evacuation, such as when we went on safari in Zambia and Botswana.
Ben, the cancel for any reason is less for when you get sick, but when your child does. We don't have children, but when my mother-in-law was in assisted living after a stroke, we bought cancel for any reason just in case something happened to her, and we had to cancel at the last minute or rush home in the middle of the trip.
I personally have never purchased travel insurance as in my experience with my parents their credit card insurance has worked extremely well. My mother lives in Latin America and had a medical emergency while in the US and since her airplane tickets had been purchased using one of her credit cards she had medical coverage for $150k. Her hospital bill was very high and fully covered by the credit card. I had some small medical...
I personally have never purchased travel insurance as in my experience with my parents their credit card insurance has worked extremely well. My mother lives in Latin America and had a medical emergency while in the US and since her airplane tickets had been purchased using one of her credit cards she had medical coverage for $150k. Her hospital bill was very high and fully covered by the credit card. I had some small medical needs when traveling abroad and paid cash and was fully reimbursed by my US health insurance plan.
My mother has been traveling a lot this year, mostly on cruises, and we bought a sub-$100 annual policy from Allianz chiefly to cover medical treatment and evacuation.
I find it fairly outlandish that you don't buy health/evacuation cover. The cost of medical transport with escort etc from Europe to the US could exceed $100,000 - are you content to pay that if the worse should happen?
My medical emergency was far more tame than some of these other commenters, but purchasing travel insurance still was able to reimburse me for thousands of dollars when I suddenly came down with appendicitis and needed emergency surgery the morning I was leaving for an overseas trip. It may be an 'ignorance is bliss' thing - until the first time you actually need it!
I have never bothered with anything but health and evacuation insurance. That costs me 13€ a year and has worked when I needed it. Everything else is just an inconvenience, not something to get insurance for.
But tbh I had not considered that of course exorbitant medical charges wouldnt be something out of the ordinary for Americans. Not a risk not encountered at home. Oh how glad I am to be from a civilized country.
I buy an annual plan from Allianz for about $500/year. I'm mostly concerned about medical evacuation, but out comes in handy in general. When my grandfather was dying, they reumbursed over $3000 for a cruise that was to late to cancel for any credit. And when I get stuck somewhere overnight, it's nice to get the reimbursement for the hotel. And little things, like recently Qatar Airways damaged my luggage cover and denied payment as...
I buy an annual plan from Allianz for about $500/year. I'm mostly concerned about medical evacuation, but out comes in handy in general. When my grandfather was dying, they reumbursed over $3000 for a cruise that was to late to cancel for any credit. And when I get stuck somewhere overnight, it's nice to get the reimbursement for the hotel. And little things, like recently Qatar Airways damaged my luggage cover and denied payment as it was the outer covering....Allianz then reimbursed the $60... easy and processed by their AI and I got the direct deposit the next day.
@Chris_ I just signed up for Allianz a couple months ago (went with their top-tier option which was also ~$500). Obviously hope to never need it but I'm also glad to hear they're reasonable with reimbursing when things happen.
After this first year I may consider dropping down to a lower level of coverage. What I got is probably overkill.
I get coverage for emergency helicopter/private jet transport home when I travel to Africa, far flung islands, or any trip including mountaineering or scuba. The cost can be hundreds of thousands of dollars, which would really suck to pay out of pocket.
They are basically a scam. They have so many exclusions and hoops for you to jump through that make it impossible to recover any funds. The health insurance ones are the worst. I read the terms and conditions of one offered through airline websites and it requires a live signature of all the physicians that treated you on your insurance claim form. So after your medical emergency abroad, you have to return to the country...
They are basically a scam. They have so many exclusions and hoops for you to jump through that make it impossible to recover any funds. The health insurance ones are the worst. I read the terms and conditions of one offered through airline websites and it requires a live signature of all the physicians that treated you on your insurance claim form. So after your medical emergency abroad, you have to return to the country you travelled to and track down all the individual physicians who treated you at the hospital to have them sign your claim form.
I never used to get travel insurance until the past few years, but then only on expensive trips or expensive stays, and that's due to getting older and having more possibly go wrong.
Example: Landed in Johannesburg on a Monday in 2023, one eye wasn't working well. Day two, go to the retinologist, find my retina is detached, he puts a stopgap in place. Day 3, fly out of Joburg for home.
I prepaid...
I never used to get travel insurance until the past few years, but then only on expensive trips or expensive stays, and that's due to getting older and having more possibly go wrong.
Example: Landed in Johannesburg on a Monday in 2023, one eye wasn't working well. Day two, go to the retinologist, find my retina is detached, he puts a stopgap in place. Day 3, fly out of Joburg for home.
I prepaid at Cape Grace in CPT, call and ask to defer the stay for a couple of months, am told no, should have purchased travel insurance. Lessons learned? 1) Eff Cape Grace, 2) Don't prepay whenever possible, 3) if prepayment is required somewhere/for some reason, get travel insurance.
7 years ago I needed an emergency helicopter in Nepal, the bring me to a clinic after I got severely sick. Costs where around $17k and I’m happy the insurance paid all. And that I’m still alive. I don’t care about delayed luggage or theft insurances, but a medical insurance can really help.
I fly/travel about once a week almost all personal. I might get stuck somewhere due to weather once, twice max a year. The price of a hotel for that night or two isn't worth the insurance. If I have an AC I can eat there.
It's not medical care you need to worry about it's medical evacuation or repatriation. That could cost in the tens of thousands at least. In my opinion, that's why you buy insurance, not for baggage delays. Annual policies are not very expensive.
You’re good.
I only insure against catastrophic loss.
The cost of a trip isn’t catastrophic.
I get an annual plan. I don't care about the trip cancellation coverage, my main focus is for the medical/evacuation if I have a medical emergency overseas, which could run in the tens of thousands of dollars. Luckily, I've never had to use it for that. Every other year on average I have a missed connection which requires me to stay overnight at a hub airport and I have consistently used the insurance to cover...
I get an annual plan. I don't care about the trip cancellation coverage, my main focus is for the medical/evacuation if I have a medical emergency overseas, which could run in the tens of thousands of dollars. Luckily, I've never had to use it for that. Every other year on average I have a missed connection which requires me to stay overnight at a hub airport and I have consistently used the insurance to cover the airport hotel/food. This saves me the hassle of trying to get a hotel voucher from the airline (if they even provide one) and also allows me to choose my own hotel, which usually means I get to stay at a nicer property directly connected to the terminal instead of taking a shuttle to a Doubletree or Four points.
I bought supplementary travel insurance once, through an airline during check out. It was the second leg of a separately ticketed itinerary.
Ended up being an amazing choice. I had to move the flight to a few days later due to extremely unusual circumstances, and thankfully the insurance covered it (and most other insurance policies likely would not have had a clause for my situation, so it worked perfectly).
Traveling without a medical insurance sounds risky... I use the one on my AMEX Platinum which does NOT require the ticket to be purchased with the card.
I make like an airplane and wing it. Im sure luck will run out sooner or later. Im looking at you, kidney stones.