You’ve said yes to the safari. The deposit is in. The kids are already talking about lions. Now someone asks: did you get travel insurance?

It’s one of the questions I get most often, and honestly, one of the hardest to answer simply. Because the right answer depends on you — how much you’re booking, how much you’re willing to gamble, and how you layer your coverage. Let me walk you through how I think about it.

Quick note: I’m a travel planner, not an insurance agent, so I can’t walk you through specific policy terms the way a licensed agent would. What I can do is tell you how I think about it for my own family, walk through how I help my clients think about it, and I can set up policies with Travelguard, Allianz and Medjet.

Supplier insurance vs. shopping around

When you book a cruise or a package tour, insurance is usually offered right there at checkout. One extra click and you’re covered. Easy.

The tradeoff: supplier insurance often gives refunds as future credits rather than cash. For some people, getting 80% back as a cruise credit after a last-minute cancellation is a great deal. For others, being locked into a future booking within a set window is less appealing than a smaller cash refund. Neither is wrong — it just depends on how you travel and how much flexibility matters to you.

If you’d rather shop around, the rest of this post is for you.

What to look at when comparing plans

Cancellation coverage — and what counts as a “covered reason”

This is the most important thing to evaluate, full stop. Policies vary wildly on what qualifies. The better ones are generous: illness of any immediate family member in the traveling party, job loss, natural disaster displacing you from your home. Read this section carefully and think about the most likely reasons you would cancel a trip.

One thing that catches people off guard: political unrest at the destination is usually excluded. Keep that in mind if you’re booking somewhere with a complicated security situation.

Cancel for Work and Cancel for Any Reason (CFAR)

Some plans offer premium riders for additional flexibility. Cancel for Work covers you if you can document that your employer is requiring you to work during your trip. I’ve purchased this for my husband, who works in tech. His schedule is not his schedule, and when something comes up, he’s expected to show up — vacation or not.

Cancel for Any Reason (CFAR) goes one step further. Your cat got sick. You changed your mind. You miscalculated when cherry blossoms would bloom. No questions asked. Most CFAR policies refund 50–85% — not 100%, because that’s not a sustainable business model — but for a penalty as small as 15%, you can get most of your money back with zero explanation required. That’s a pretty good deal.

Two catches: CFAR plans are significantly more expensive than standard ones, and you usually have to purchase within two weeks of your initial deposit. This is exactly why I email clients immediately after they’ve confirmed and placed a deposit. I want you to have the option before the window closes. It’s the kind of thing that’s easy to miss when you’re booking on your own and just excited to have finally pulled the trigger.

Trip delay and trip interruption

This is meatier than people realize. How many hours does your flight have to be delayed before coverage kicks in? What does it cover — just a hotel, or also missed tours? What about trip interruption, where you’ve already arrived but something happens and you can’t finish the trip? Review this section carefully.

Lost or delayed luggage

Everyone has a story. Mine involves my husband, an overnight flight to Turkey, a lost bag, and the ugliest American flag shorts from a street vendor. He was being cheap. If he’d had coverage that gave him a real shopping budget, maybe he would have bought something he actually wanted to wear. All kidding aside — luggage gets delayed or lost more than it should, and a rocky start can derail the whole mood of a trip. It’s worth knowing you have a budget to recover quickly.

Medical coverage — and why this actually matters more than you’d think

Most standard travel insurance plans include around $500,000 in medical coverage, which sounds like a lot. And for most people, it is.

But as a physician — infectious disease is my specialty — I’d push you to not just skim past this section. A few things worth checking: How does the plan handle pre-existing conditions? What’s covered if you need emergency care in a country with limited medical infrastructure? If you’re traveling somewhere remote, what’s the protocol for getting you to a hospital?

If you have significant health considerations or are traveling to a destination with limited medical facilities, read this section of any plan carefully and don’t just assume the standard coverage is enough.

Evacuation insurance — this is the one most people skip and shouldn’t

This is separate from travel insurance and separate from medical insurance, and I think it’s the most underappreciated coverage out there.

Medjet is what I use. It does not cover your cancelled tours, your hotel, or your medical bills. What it covers is the cost of evacuating you back to a hospital of your choosing.

That last part matters to me. I don’t just want to be taken to the nearest hospital in Buenos Aires if I break a leg hiking in Patagonia. That’s not a judgment on the quality of care in Argentina — I just want to go home, to the Bay Area, to where my colleagues are. I want to be able to say: take me back to Stanford.

Medjet Assist covers medical evacuations. I upgraded our family this year to Medjet Horizon, which also covers political unrest, terrorism, kidnapping, and natural disasters. I hope I never have a story to tell you about using it. But I sleep better knowing I have it.

Medjet is sold in 1, 2, 3, and 5-year periods — not per trip. Anything that happens during that period is covered.

Annual plans vs. trip-specific plans

You don’t have to buy a new policy for every trip. Annual plans — I use Allianz — cover you for a full year without requiring you to specify dates or destinations in advance. They usually have a cap (around $15k), which keeps them affordable.

Here’s how I think about the math: if I book a Disney cruise for $10k and I have a $15k annual plan, I may not buy a separate policy for that trip — my annual coverage handles it. But if I book a $30k safari, that exceeds my annual cap. In that case, I might buy a $15k trip-specific policy to sit alongside my annual plan, so I’m fully covered.

Annual plans also cover the trips that fly under the radar — a ski weekend two states over, Christmas at the grandparents’ house. Most plans cover anything beyond a certain distance from home (150 miles is common). It adds up to meaningful coverage you didn’t have to think about.

The part where I tell you how to think like a gambler (responsibly)

When clients ask me “what would you do?” — this is what’s actually going through my head:

  1. What’s already cancellable? Refundable flights, hotels with flexible cancellation, tours you can cancel 24 hours out — none of that needs to be insured. Strip it from the calculation.

  2. What does your credit card cover? Premium travel cards like Chase Sapphire Reserve or Amex Platinum have real travel protections built in. I wouldn’t rely on them entirely, but they exist and they count.

  3. How much are you willing to lose? The odds of a full trip cancellation are low. If something truly catastrophic happened, losing some trip costs would probably be the least of your concerns. So ask yourself: what’s the number I could absorb without it stinging too badly? Maybe it’s $3k. Maybe it’s $5k. Whatever that number is, you can deduct it from the coverage you need — which makes the policy cheaper.

  4. Layer your annual plan on top of all of the above. Once you’ve subtracted what’s cancellable, what your credit card covers, and what you’re willing to absorb, what’s left is what you actually need to insure for.

That’s the math. It’s never a simple answer, which is why I can’t give you one in a single sentence — but now you have the framework.

Questions? Reach out. This is the kind of thing I love to think through with clients before a big trip, and it’s always easier to sort out before you’ve booked everything.