MR2b: Mini-Retirement Prep - How we chose the right insurance for our travel year (spreadsheet provided)

TL;DR we chose SafetyWing’s Essential Plan and pay $112/mo for two people ($1,351 annually). Isn’t that crazy, my fellow Americans? I have successfully filed a claim thus far and you can skip to this section to read about it.

If you don’t know, I’m a little extra when it comes to research and documentation. I also take pride in how I organize information. My spreadsheets are probably way too complicated for the average person’s patience to put together, but they benefit my (and Kyle’s) life in many ways. I’ve also found that when doing something very overwhelming, it’s hard for people to know where to start without a visual guide. So, I hope the below structure and information may help you.

Research

I read quite a few articles on this and wrote down the common companies I saw. I ultimately researched six different companies and moved forward with SafetyWing’s Essential plan. This research was conducted in February 2025, and policies may have changed since.

The four companies that we didn’t qualify for:

• Luma Health - must be based in Southeast Asia

• TrueTraveller - can only insure residents in UK and Europe

• World Nomads and Hey Mondo - only works for defined “Trips”. Policies note a max number of days per trip meaning we would have to go back to our home country

The two companies that we did qualify for were SafetyWing and IMG. Within IMG, I was comparing two of their plans (Outreach and Patriot Life).

Snapshot of side-by-side comparison spreadsheet - click to make a copy

Criteria & Selection

Once I looked at enough policies, I could tell the overarching categories they did/did not cover. I wanted to make sure Kyle was comfortable with what I selected but I didn’t want to review every policy detail with him. So, I asked him to rank the following criteria (luckily, they aligned with my rank).

1. Post Medical Care

2. Dental

3. Action Sports Coverage (with respect to skiing, though it looks like downhill skiing is covered by most policies but things like skiing off-piste or ski jumping are not)

4. Trip Coverage

5. Preventative Care

Quick aside: I did have a dental emergency on week 2 of 4 during our trip to Italy in 2023. This is definitely in our memory when we ranked dental care as #2. 

We ultimately chose SafetyWing because they had higher emergency dental limits and a few more travel-related coverages. Other considerations:

• The difference in overall coverage limits ($250K vs $500K) was not important to us as we believe medical care outside of the U.S. is significantly cheaper

• Price was about the same across all policies, so that was not a factor

• None of these policies covered preventative care, but we weren’t looking for that

I was originally going to pay annually but SafetyWing was pushing us to pay per month. I ended up choosing monthly because we don’t know if our mini retirement will last a full 12 months.

Filing a Claim

It looks like there isn’t a lot of information online on actually filing a claim. I only found one article for good reference. My experience was great and I’ll detail the actual visit in a future blog post.

Day 0 - Doctor visit and prescription pickup

Day 1 - Submitted claim

Day 3 - Received full diagnosis summary (oops) and emailed additional attachment

Day 4 - Claim approved 100% of costs

Day 5 - Claim paid out 

I was emailed my prescription details pretty soon after my visit but the diagnosis documentation came 3 days later. I did submit the claim without the diagnosis on accident but was able to email it later. In total, I paid $253.13 (€100 for the visit, €80 for flu, COVID, and strep tests, and ~€36 for the medicine). 

The form was pretty straightforward with the exception of the “Tell Us What Happened” portion. I kept pretty good details of the dates and symptoms of my illness as I was journaling daily. I word-vomited it all to ChatGPT so it could give me a professional summary to improve the likelihood of getting reimbursed. My main emphasis was that I did not have this illness before the policy. 

My personal experience was fantastic with Safetywing, given the claim was fully approved. It was also very nice to not have to pay a deductible. By this point, we had paid $226 for coverage, thus making buying insurance worth it. I am not affiliated with Safetywing, just a happy customer so far into our trip. If you would like to try them out yourselves, use my referral link!