About CoverTrip
By Damian Tysdal, licensed insurance producer, Massachusetts NPN 8615978 · Updated 25 September 2026
CoverTrip is a travel insurance comparison site, run by a licensed agent, that shows travelers every top plan side by side, priced for their trip, at the same price as buying direct.
It has been doing that job since 2006. Every review, guide and answer on the site is written in plain words and checked against the policy itself.
What CoverTrip does
Compares travel insurance plans
Enter your trip once. Plans from the top insurers come back priced for your dates, your ages and your trip cost. You can filter for what matters to you, like cancel for any reason or a pre-existing condition waiver, and compare your favorites side by side.
Reviews every company on the comparison
We review each insurer from its actual policy wording, not its marketing page. Each review says who the company is good for, who should skip it, and what the fine print says about the things people get caught by. Read the reviews.
Explains the parts that trip people up
Guides and short answer pages cover the real questions: cruises, pre-existing conditions, what trip cost to enter, Medicare abroad, how claims work. Each one is checked against the policies and carries the date it was last checked. Start with the guides.
Sends one useful email a week
Safe Travels goes out every Friday. One real claim or reader question, and what to do about it. No sales pitch. Sign up at the bottom of any page.
What makes CoverTrip different
A licensed agent since 2006, not a checkout box
The box on an airline or cruise site sells one plan and explains nothing. CoverTrip is run by a licensed insurance producer who has compared and written about these policies for 20 years. The reviews are signed, and the license number is at the top of this page.
The same price as buying direct
Travel insurance prices are filed with state regulators, so a plan costs the same here as it does from the insurer. The insurer pays us a commission when you buy. There is no fee, and no plan is shown or hidden because of what it pays us.
Help if a claim is denied
Every policy bought through CoverTrip comes with the Zero Complaint Guarantee from our partner Squaremouth. If a claim is denied and you think that is wrong, licensed claims adjusters look at it and take it up with the insurer for you, free. You do not get that buying the same plan from the insurer’s own site.
Checked against the policy, not the brochure
We keep the full policy wording for every plan on the comparison, 54 plans in all. Every specific claim on the site is checked against those documents, and re-checked when the wording changes. Where we give a number, it is a count from the policies, not a guess.
No fake deadlines
Many sites push you to buy today. We do not. A policy can be bought any time before you leave. Only two upgrades, the pre-existing condition waiver and cancel for any reason, have a window, and we say so plainly instead of using it to rush you.
Who uses CoverTrip
- Travelers over 60, especially cruisers, who need real medical and evacuation coverage outside the US.
- People taking a big international trip who want to know what a plan covers before they pay for it.
- Anyone with a pre-existing condition who needs to know how the waiver works and when to buy.
- Families and groups booking months ahead who want cancellation coverage that actually pays.
- People who just put down a deposit and want a straight answer on what to do next.
The person behind CoverTrip
My name is Damian Tysdal. I have sold, compared and written about travel insurance since 2006. I am a licensed insurance producer in Massachusetts (NPN 8615978), with the life, casualty, accident and health, property and travel lines, and I run CoverTrip from Hingham, on the South Shore of Massachusetts.
I started the first travel insurance blog in 2006 because every site on the subject existed to sell a policy and none of them explained one. That blog, travelinsurancereview.net, grew to more than 100,000 visitors a month. In 2021 it became CoverTrip, a name people can remember and spell, rebuilt around the side-by-side comparison.
I have been the customer too. When my son came down with the flu a few days before a family Christmas trip, the policy we had bought paid back every dollar, flights and lodging included. The coverage works, but only if you understood what you were buying. That is the whole reason this site exists.
How CoverTrip works
- Compare. Enter your trip on the comparison and every top plan comes back priced for it. Free, no account.
- Buy. Click Buy Now and you finish on our partner Squaremouth’s secure checkout. Your policy arrives by email. Most plans give you 10 to 15 days to read it and cancel for a full refund.
- Get help. Squaremouth’s licensed agents answer questions about choosing or buying a plan at 1-800-240-0369, 8am to 10pm ET, every day. Claims go to your insurer. Questions about the site go through our contact page, answered within two business days.
- If a claim goes wrong. The Zero Complaint Guarantee is there for every policy bought here.
The full explanation of how CoverTrip works, including how we get paid.
Key facts
| Company | Travel Insurance Review Inc., doing business as CoverTrip |
|---|---|
| What it is | A travel insurance comparison site, plus reviews, guides and a weekly newsletter |
| Founded | 2006 as travelinsurancereview.net; renamed CoverTrip in 2021 |
| Founder | Damian Tysdal, licensed insurance producer in Massachusetts (NPN 8615978), licensed since 2006 |
| Based in | Hingham, Massachusetts |
| Website | covertrip.com; the comparison runs at quotes.covertrip.com |
| Plans compared | 54 plans from the top US travel insurers, with a review of every company |
| Cost to you | Free. The insurer pays a commission when you buy. Prices are the same as buying direct |
| Contracts | None. Buy a plan or do not |
| Checkout and support | Squaremouth, a licensed agency; agents at 1-800-240-0369, 8am to 10pm ET, every day |
| Claims help | Zero Complaint Guarantee on every policy bought through CoverTrip, from Squaremouth |
| Newsletter | Safe Travels, every Friday |
| Where else | YouTube, Facebook, Instagram and TikTok, all under CoverTrip |
| Contact | covertrip.com/get-in-touch; replies within two business days |
Questions people ask
Is CoverTrip an insurance company?
No. CoverTrip compares plans from the insurers and explains them. The policy is with the insurer, and the purchase is completed by our partner Squaremouth, a licensed agency.
Does it cost more to buy through CoverTrip?
No. Travel insurance prices are filed with state regulators, so a plan costs the same here as from the insurer. The insurer pays us a commission.
Is CoverTrip the same as Squaremouth?
No. CoverTrip is an independent site run by a licensed agent. Squaremouth powers the comparison and completes the purchase, and its Zero Complaint Guarantee covers every policy bought here.
Who writes the reviews?
Damian Tysdal, a licensed insurance producer in Massachusetts since 2006. Each review is checked against the policy wording and carries the date it was last checked.
Can I call CoverTrip?
Questions about choosing or buying a plan go to Squaremouth’s licensed agents at 1-800-240-0369. Questions about the site go through the contact page and are answered within two business days.
Do you take the insurer’s side?
No. No plan is shown or hidden because of what it pays us, and the reviews say who should skip a plan as plainly as who should buy it.