Squaremouth Travel Insurance Review: Costs, Coverage, and More
Squaremouth makes shopping for travel insurance less painful. It’s legitimate, easy to use, and gives you coverage options that fit your trip and budget.
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Written byAmy Beardsley
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3+ years writing about auto, home, and life insurance
7+ years in personal finance and technology
Amy specializes in insurance and technology writing and has a talent for transforming complex topics into easy-to-understand stories.
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Edited byBecky Helzer
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Becky Helzer is an editor at Insurify. She loves helping writers express their ideas clearly and authentically. With a diverse background in editing everything from curriculum and books to magazine articles and blog posts, she’s worked on topics ranging from home finance, insurance, and cloud computing to the best tools for home improvement.
A proud graduate of Colorado State University with a degree in technical journalism, Becky lives in Fort Collins, CO, with her husband and their two spoiled rescue dogs.
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Table of contents
Squaremouth is an online comparison platform that lets you shop for travel insurance from hundreds of companies.[1] Instead of visiting individual websites, you can compare coverage and prices in one spot.
Nearly one in four flights didn’t arrive on time during the first half of 2025, according to the U.S. Bureau of Transportation Statistics.[2] Add in medical emergencies and lost luggage, and you’ll see how Squaremouth travel insurance can help protect your dream vacation from becoming a financial nightmare.
Quick Facts
Squaremouth has transparent pricing and no extra fees.
Squaremouth’s Zero Complaint Guarantee promises honest claims handling.
You can choose from travel insurance that covers only medical emergencies to plans that cover trip delays or cancellations.
Our take on Squaremouth travel insurance
Squaremouth is a solid choice for comparing travel insurance companies without visiting a dozen websites. We’d recommend Squaremouth, especially if you’re not sure which company to choose. Since it’s a travel insurance marketplace and not an insurance company, you can shop multiple insurers in one place.
Depending on your travel plans, you can choose from single-trip travel insurance, annual coverage, or specialized options for cruises and flights. The site’s comparison tools make it easy to see what you’re getting.
Plus, Squaremouth’s Zero Complaint Guarantee means it’ll investigate if you run into problems with a claim.
Customer reviews are positive on Trustpilot and Google. Complaints are rare on the Better Business Bureau (BBB) and usually stem from confusion about what’s covered or the policy itself.
But these issues are common in the travel insurance industry and aren’t specific to Squaremouth. Overall, reviewers say they like the helpful comparison process and customer service.
Pros and cons of Squaremouth travel insurance
Pros
Can compare dozens of insurers in one place
Zero Complaint Guarantee promises to investigate claims you believe were unfairly denied
Fast, user-friendly online quoting and purchase process
Cons
Third-party insurance companies issue and service policies
Claims process varies depending on insurer
Number of travel insurance options can be overwhelming
Squaremouth coverage for single trips
Squaremouth has several single-trip travel insurance options, which you can compare in the table below.
 | Comprehensive | Group | Travel Medical | Flight | Cruise |
|---|---|---|---|---|---|
| Emergency medical care | Yes | Yes | Yes | Yes | Yes |
| Medical evacuation | Yes | Yes | Yes | Yes | Yes |
| Sports and adventure | Yes | No | No | No | Limited |
| 24/7 travel assistance | Yes | Yes | Yes | Yes | Yes |
| Travel delay | Yes | Yes | Limited | Limited | Yes |
| Baggage delay | Yes | Yes | No | Limited | Yes |
Squaremouth single-trip travel insurance policies can include medical coverage and trip cancellation protection. For the most robust protection, policies can also include adventure activities and sports coverage to protect against injuries, lost or damaged equipment, and lost tee times.
Group travel insurance can save you money by covering multiple people under one policy. With it, you get core travel accident insurance protection, including medical care, emergency assistance, and travel and baggage delay coverage.
Ideal for large families, it’s available only to groups of 10 or more traveling to the same place.
Travel medical insurance is spare, covering only medical emergencies. You get emergency medical care and evacuation if needed, along with Squaremouth’s promised 24/7 support. Trip cancellation coverage applies only for medical reasons, and there’s no baggage protection.
If your flight gets delayed or canceled, flight insurance pays for your hotel, meals, and other costs you didn’t plan for. It can also cover medical emergencies, including hospital visits, doctor visits and prescriptions, and baggage loss and delay.
A medical evacuation while in the middle of the ocean can cost quite a bit — helicopter rescues from ships aren’t cheap. Cruise insurance policies often have higher coverage limits for this scenario. These plans provide emergency medical assistance and also protect you if you miss your ship’s departure due to a delayed flight.
Protect Your Trip with Travel Insurance
Find a plan to fit your trip and travel style
Squaremouth annual travel insurance coverage
Squaremouth also offers a couple plans for annual travel insurance.
| Annual Basic (Travel Medical) | Annual Comprehensive (Medical and Cancellation) |
|---|---|---|
| Emergency medical care | Yes | Yes |
| Medical evacuation | Yes | Yes |
| Medical repatriation | Yes | Yes |
| 24/7 travel assistance | Yes | Yes |
| Travel delay | No | Limited |
| Baggage delay | No | Limited |
Annual travel medical coverage through Squaremouth covers your health but not your trip costs. It’s a good choice if you book travel with rewards points or refundable rates and aren’t concerned about non-refundable expenses.
Plans typically include emergency medical care, medical evacuation, and repatriation back to the U.S. All plans through Squaremouth also include 24/7 travel assistance in case you need help navigating a foreign healthcare system.
Annual comprehensive plans give you medical coverage benefits plus travel and baggage delay protection. If you travel often, book in advance, and opt for non-refundable reservations, a comprehensive plan can pay for itself quickly.
It’s worth noting that travel cancellation and trip interruption coverage are rare in an annual trip protection plan. Read the fine print carefully to understand what your plan covers and excludes.
What Squaremouth doesn’t cover
You’ll likely have exclusions with any travel insurance policy you purchase. The protection you get depends on the company you choose and the policy type you pick.
In general, Squaremouth trip protection plans don’t cover:
Injuries from high-risk activities
Known events or those likely to occur
Named storms or disasters (if named before you bought coverage)
Wars or riots
Trips longer than 90 days
Voluntary flight cancellations
Sports and adventure equipment, unless specifically added
Cost of Squaremouth travel insurance
Squaremouth travel insurance costs roughly $21 per day, according to its website. But how much you pay depends on several factors.
The table below shows several traveler profiles to illustrate how much travel insurance costs for a one-week trip to Italy:
Traveler Profile | Trip Cost | Policy Cost |
|---|---|---|
| 26-year-old male traveling alone | $3,000 | $113 |
| 35-year-old couple | $5,500 | $320 |
| Family of four (two kids younger than 13) | $8,000 | $370 |
Your age, trip length, destination, and total trip cost influence your travel insurance cost. A policy for a $3,000 solo trip is cheaper than insuring an $8,000 family vacation because less money is at risk. Older travelers often pay more for travel insurance, since health problems tend to become more common with age.
Where you’re going matters, too. Your premium may be higher if you’re traveling somewhere with expensive healthcare, extreme weather, or frequent natural disasters.
Your plan type and deductible choice also affect price. Basic medical-only policies cost less than plans that cover cancellations, delays, and sports and adventure activities.
And if you add extras, like cancel for any reason coverage or pre-existing condition waivers, your premium will increase even more.
Who is Squaremouth travel insurance best for?
Squaremouth travel insurance is a good choice for travelers of all kinds, but some may get more out of it than others. Families booking trips with many prepaid costs — like Disney vacations, cruises, or international travel — benefit from good cancellation coverage.
But frequent business travelers might be better off with annual business travel insurance instead of buying individual plans.
The key is to match your travel insurance to your travel style. For instance, if your travel plans include ski trips, scuba diving, or mountain biking, look for travel insurance that offers sports and adventure coverage.
And if you worry about things going wrong, a comprehensive plan that costs more up front can be worth it for the reassurance that it provides.
Customize Your Travel Insurance Plan
Save on trip insurance designed to fit your needs
How to buy a Squaremouth travel policy
Planning a trip means juggling details like flights, hotels, and things to do. Travel insurance reviews show that Squaremouth makes finding travel insurance easier.
The best time to look for coverage is right after booking your trip. You can buy travel insurance anytime before you leave, but waiting more than 15 days after booking can limit the protection you get from your plan.
Here’s how the quote process works:
1. Figure out what you need
Consider your travel risks, such as trip cost, whether you want medical coverage, any expensive gear you’re taking, and the number of flight connections you have.
2. Get a quote
Enter your destination, trip dates, traveler ages, and trip cost.
3. Compare your options
Sort policies by price, read the details, and use filtering options to narrow down travel insurance categories that fit your travel needs.
4. Buy your policy
Once you choose your plan, you’ll get instant policy confirmation by email with all the important information.
If you have questions, you can also call 1 (800) 240-0369. Customer service representatives are available daily from 8 a.m. to 10 p.m. Eastern time.
How to file a claim with Squaremouth
If something goes wrong on your trip, you’ll file a claim with the travel insurance company that sold you the policy — not Squaremouth. Each company has a slightly different process, but most let you file online, by email, or through regular mail.
Here’s a list of the documents you might need:
Credit card statements
Receipts for expenses
Medical paperwork
Police reports
Your travel schedule and bookings
Proof of payment for your trip
Any other relevant documents
Most travel insurance companies ask that you file your claim as soon as possible. The timeline depends on your policy, so check your paperwork to see if there’s a deadline.
Keeping digital copies of all relevant paperwork helps you quickly gather what you need and makes the claims process easier.
Squaremouth travel insurance FAQs
Before purchasing a Squaremouth travel policy, you might have some questions. Below are answers to frequently asked questions travelers have.
Is Squaremouth travel insurance legit?
Yes. Squaremouth is a legitimate travel insurance comparison site that’s been around since 2003. The platform helps you compare hundreds of policies on one easy-to-use website.
Does Squaremouth cover flight cancellation?
Squaremouth itself doesn’t provide coverage, but many policies you can buy through the platform cover flight cancellation. Look for comprehensive plans or specific flight insurance that includes trip cancellation benefits.
Can you buy travel insurance after booking a flight?
Yes. You can buy travel insurance anytime before your trip starts. But waiting more than 15 days after your first prepaid booking might disqualify you from certain plan benefits.
Does travel insurance cost more the closer you get to your trip?
Not necessarily. Insurers base travel insurance premiums on trip cost, traveler age, destination, and length — not when you buy it. But buying late can mean you lose access to benefits like cancel for any reason coverage or a pre-existing condition waiver.
When does it make sense to purchase travel insurance?
Travel insurance makes sense when you spend significant money on non-refundable trip costs.[3] It’s also a smart investment for international travel — especially if travel disruptions are likely, your health insurance doesn’t apply, or medical care is costly.
Is travel insurance worth it?
It depends on your risk tolerance. Travel insurance is worth it if you’re spending thousands on a vacation and can’t afford to lose that money. But for cheaper, flexible trips, you might decide to skip it.
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Sources
- Squaremouth. "About Squaremouth."
- United States Department of Transportation. "Bureau of Transportation Statistics."
- Insurance Information Institute. "Should you buy travel insurance?."
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Amy BeardsleyInsurance Writer
Amy is a personal finance and technology writer. With a background in the legal field and a bachelor's degree from Ferris State University, she has a talent for transforming complex topics into content that’s easy to understand. Connect with Amy on LinkedIn.
Amy has been a contributor at Insurify since September 2023.
Becky Helzer is an editor at Insurify. She loves helping writers express their ideas clearly and authentically. With a diverse background in editing everything from curriculum and books to magazine articles and blog posts, she’s worked on topics ranging from home finance, insurance, and cloud computing to the best tools for home improvement.
A proud graduate of Colorado State University with a degree in technical journalism, Becky lives in Fort Collins, CO, with her husband and their two spoiled rescue dogs.
