The Trip Insurance Roadmap I send to friends and family
Enter your email and I’ll send you the Roadmap, the Cruise Coverage Guide, and the other downloads I mention in my videos.
- The Trip Insurance Roadmap: what to buy, when to buy it, and what to skip (37 pages, 2026 edition)
- Two plans worth a look right now: the ones I have noticed for pricing and value
- The Cruise Coverage Guide: what cruisers miss most
- Plus the bonus downloads I mention in my videos
Damian Tysdal, licensed travel insurance agent since 2006. I built CoverTrip so travelers can compare plans without a sales call.
Where should I send it?
Enter your email and it lands in your inbox in about a minute.
Check your inbox
The Roadmap is on the way. If you don’t see it in a couple of minutes, check spam or promotions.
Download it nowWhat is inside the 2026 edition
Thirty-seven pages, written in plain English. Every number in it was checked against the policy documents of the 54 plans CoverTrip compares, in September 2026.
A PDF that reads on a phone or a laptop
The basics, fast
What can go wrong on a trip, the myths you have been told, and which type of plan fits your trip.
The small print that matters
Six checks that decide whether a plan pays. One page you can hold next to any policy.
Two common mistakes
Waiting to buy, and buying at checkout. Both are easy to fix once you know why.
Who pays if you get sick abroad
Medicare, Medigap, Advantage plans, employer plans and credit cards, side by side.
Pre-existing conditions, in plain words
How the look-back works, and the waiver that makes it go away on 53 of 54 plans.
The buying roadmap
The just-tell-me-what-to-buy option, with two plans I have noticed for pricing and value, and the do-it-yourself way to compare.
Three bonuses
Hurricane season, cruises, and how to make a successful claim, including the Zero Complaint Guarantee.
Also in your inbox
The Cruise Coverage Guide, and the bonus downloads I mention in my videos.
A taste: the Small Print Scorecard
Six lines. Check them against any plan you are looking at. The Roadmap explains each one and shows where to find it.
| Check | What passes | Why it matters |
|---|---|---|
| Travel delay trigger | 6 hours or less | Decides whether a normal delay ever pays. Runs from 3 to 24 hours across the 54 plans. |
| Emergency medical | $100,000 per person or more, primary | The hospital gets paid first, by the plan. |
| Medical evacuation | $250,000 per person or more | The one bill nobody has in the bank. |
| Hurricane warning | Named as a reason to cancel | Lets you cancel before the storm hits. 17 of 54 plans have it. |
| Pre-existing look-back | 60 days | Shorter is better for you. 22 of 54 plans use 60 days; 21 use 180. |
| Weather cancellation trigger | Low, around 6 hours | A 48-hour trigger almost never pays. Six hours often does. |
Source: the policy documents of the 54 plans CoverTrip compares, September 2026. Plans change. Where the Roadmap and your policy disagree, your policy wins.
Who this is for
It was written for the people who ask me about trip insurance at dinner.
You just booked a big trip
A cruise, a tour, a trip abroad with the family. Real money is on the line and you want it protected without overpaying.
You are on Medicare
Medicare does not travel with you. The Roadmap shows who pays if you get sick abroad, and what a good medical plan costs.
You were offered a plan at checkout
The cruise line, the airline and the booking site all want to sell you one. The Roadmap shows what those plans leave out.
Why would you trust me about trip insurance?
My name is Damian Tysdal. I have sold, compared and written about travel insurance since 2006, and I am a licensed travel insurance agent. I started CoverTrip because every site on the subject existed to sell a policy, and none of them explained one.
Today more than 270,000 people follow CoverTrip on YouTube and Facebook. The site shows every top plan side by side, priced for your trip, at the same price as buying direct.
I have also been the customer. When my son got the flu a few days before a family Christmas trip, the policy we had bought paid back every dollar. The coverage works, but only if you understand what you are buying. That is what the Roadmap is for.
Questions people ask before they sign up
Is it really free?
Yes. No card, no trial, no catch. Enter your email and the Roadmap lands in your inbox in about a minute.
What happens after I sign up?
You get the Roadmap right away. Over the next two weeks you get a few short emails that walk through when to buy, where to buy, and what to do if you ever have to claim. Unsubscribe any time, with one click.
Do you sell insurance?
CoverTrip is a comparison site. You compare the plans yourself and buy the one you want, at the same price as buying from the insurance company. The insurance company pays CoverTrip a commission. You pay nothing extra.
Is there a deadline to buy trip insurance?
No. You can buy a good plan right up to the day you leave. Two optional extras, the pre-existing condition waiver and Cancel For Any Reason, are only offered in the first 14 days after your first trip payment. The Roadmap explains both.
Get the Roadmap
Free, 37 pages, checked against the 54 plans CoverTrip compares. Your email, and it is on the way.
Send Me The RoadmapReady to compare plans now? See every plan priced for your trip →
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