I used to be that person who clicked “No, I’ll take the risk” on the checkout page. I thought travel insurance was just a clever way for Carnival or Royal Caribbean to squeeze another $150 out of me so their shareholders could buy a third vacation home. Then 2017 happened. I was on the Carnival Splendor, and my dad’s blood pressure spiked to a level that made the ship’s doctor look like he’d seen a ghost. Long story short: we had to bail, I lost $2,400 in non-refundable bookings, and I spent three hours crying in a humid parking lot in San Juan. Never again.
The $20,000 mistake you’re probably making
Most people think the “best” insurance is whatever the cruise line sells you during checkout. It’s convenient. It’s right there. It’s also a total scam. I might be wrong about this—maybe some people love the simplicity—but in my experience, the coverage limits on those “in-house” plans are pathetic. They usually cap medical at like $10,000 or $25,000. That sounds like a lot until you realize a helicopter ride from a ship to a hospital in Miami starts at $20,000. If you have a heart attack in the middle of the Caribbean, that $25,000 policy is about as useful as a paper napkin in a knife fight.
I spent about 4 hours last month digging through 12 different policies on Squaremouth, and I found that the average “cruise-specific” rider adds a 14.2% markup to the premium for almost zero extra benefit. You’re paying for the convenience of not having to open a second tab in your browser. Don’t be that person.
My completely irrational hatred for Allianz

I know everyone recommends Allianz. They’re the big dog. But I refuse to use them. I don’t care if they have 5-star reviews or if your travel agent swears by them. A few years ago, I tried to file a claim for a delayed flight that caused me to miss the embarkation in Fort Lauderdale. Their claims portal looked like it was designed in 1998 by someone who actively hates human beings. I spent three weeks uploading PDFs only for them to tell me my “proof of delay” wasn’t on the right letterhead. It was petty, it was bureaucratic, and I’m a grudge-holder. I’ve bought the same AIG Travel Guard policy four times now just because their website doesn’t make me want to throw my laptop out a window. I don’t care if something better exists. I’m staying put.
What I actually buy now (The blunt truth)
If you want the actual best cruise vacation insurance, you stop looking at the cruise lines and you look at third-party aggregators. I usually end up with AIG Travel Guard or Nationwide. Why Nationwide? Because their “Luxury” plan (which isn’t even that expensive) has a $250,000 medical evacuation limit. That’s the “I don’t want to go bankrupt because I tripped on a lido deck chair” insurance.
- AIG Travel Guard: Best for when you have weird pre-existing conditions you need to cover.
- Nationwide (Cruise Luxury): Best for high medical limits.
- Trawick International: Usually the cheapest if you just want the bare minimum to satisfy a requirement.
The policy limits are—actually, let me put it differently. It’s not the dollar limit that kills you, it’s the definitions. I used to think the “Cancel for Any Reason” (CFAR) add-on was a waste of money. I was completely wrong. If you don’t have CFAR, and you decide not to go because your cat died or your boss is being a jerk, you get zero dollars back. Standard insurance only cares if you’re dying or the ship is sinking. CFAR is the only thing that actually protects your sanity.
Pro tip: You usually have to buy the insurance within 14 to 21 days of making your first deposit to get the pre-existing condition waiver. If you miss that window, you’re basically hosed.
The part nobody talks about
Every blog post tells you to buy insurance. Nobody tells you how much it sucks to actually use it. Even the “best” companies will make you jump through hoops. You need to keep every single receipt. I’m talking about the $4 bottled water you bought because you were dehydrated from the flu. I’m talking about the Uber receipt from the port to the hotel. If you don’t have a paper trail, they will find a way to deny you. It’s their job. It’s a cynical business.
Anyway, I’m rambling. The point is that you should buy a third-party policy with at least $100,000 in medical evacuation coverage. Anything less is just gambling with your retirement fund. I’ve seen people get stuck in foreign ports because they couldn’t pay the hospital bill upfront. It’s ugly. It’s not like the commercials.
I still wonder if I’m overpaying for the CFAR stuff, though. Is it worth an extra $200 just for the peace of mind? I honestly don’t know. But after that day in San Juan, I’d rather lose the $200 than the $2,000. Buy the damn insurance.