Squaremouth is a prominent US-based travel insurance marketplace. Learn pros, cons, pricing, services, and more.

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Squaremouth 2024 Review

Joe Cortez

Award-Winning Writer, Digital Communications Leader

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Squaremouth Review

Arguably the largest travel insurance marketplace operating in the United States, Squaremouth offers 90 unique travel insurance plans from over 30 different insurance companies. No matter where you decide to go and what you decide to see, there’s a good chance Squaremouth offers a policy that will cover your situation.

With so many choices, searching for the right travel insurance plan can quickly become overwhelming. How can you ensure you’re getting the best level of protection for your money? Moreover, if you do end up with a claim, who can you turn to for help?

In this article, we’ll cover everything that Squaremouth offers: What insurance companies they work with, the types of policies you can buy, and where to go if you need to file a claim.

What is Squaremouth?

Squaremouth was founded in 2003, making them one of the oldest travel insurance marketplaces online. As an insurance agency, the company is licensed to sell insurance products in all 50 states and the District of Columbia. Because state regulations vary, the number of insurance policies may be limited based on your primary residence.

One of the advantages of buying through Squaremouth is their “Zero Complaint Guarantee.” If you are not satisfied with a claim, their team of claims adjusters will review the case and mediate on your behalf. Although they cannot guarantee that the claim will be paid out, they will remove any insurance company that does not fulfill claims to their satisfaction. While the guarantee offers an additional layer of assurance, Squaremouth doesn’t publish data on what percentage of claims decisions are overturned through their intervention.

The company offers four different categories of travel insurance, which may include medical care coverage. However, these plans are usually not compliant with the Affordable Care Act regulations, because they are temporary in nature and are designed to cover travelers when they are away from their primary residences. Therefore, you should not expect a travel insurance plan to cover routine care, nor prescription medications while you are home.

Squaremouth Travel Insurance Options

As a travel insurance marketplace, Squaremouth offers policies from 32 different insurance providers. Some of the well-known names they offer plans from include:

  • April Travel Protection
  • AXA Assistance USA
  • Berkshire Hathaway Travel Protection
  • Generali Global Assistance
  • GeoBlue
  • Seven Corners
  • Tin Leg - a Squaremouth Brand
  • Travelex Insurance Services
  • TripAssure - a Trip Mate Brand

While most marketplaces do not offer their own insurance policies, Squaremouth offers a line of plans under the Tin Leg brand. With six different levels of coverage, the Tin Leg policies are underwritten by either Berkshire Hathaway Specialty Insurance Company with a AM Best Rating of A++ (Superior), or Starr Indemnity & Liability Company with a AM Best Rating of A (Excellent). All other plans are underwritten by their specialty insurance providers.

Which Travel Insurance Plans Does Squaremouth Offer?

Squaremouth plans can be broken down into four categories: Single trip policies, annual or multi-trip policies, adventure and sports policies and group policies for 10 or more travelers. Each one offers a different level of coverage, based on your trip length, destination, and level of coverage you prefer.

  • Single Trip Policies: As the name suggests, single trip policies only cover the start and finish of one outing away from home. These travel insurance plans can cover trips that start and end in the United States, or journeys to one or several nations. A single trip policy will often cover benefits for trip cancellation, trip interruption, baggage delay or loss, and limited medical coverage. Single trip coverage is best for individuals or groups who are traveling internationally, and want the peace-of-mind to know that in the event of an emergency, their property and health may be protected.
  • Annual/Multi-Trip Policies: For travelers who plan on taking several trips across the United States or around the world every year, Squaremouth also offers annual policies. Also known as multi-trip policies, these plans are best for those who know they will be traveling more than 50 miles from their residence several times each year. Although these plans usually offer the same coverage as single trip policies for up to 364 days, they may come with annual claims limits as well.
  • Adventure and Sports Policies: For thrill seekers, most travel insurance plans won’t cover their activities of choice. Squaremouth offers a line of plans specifically designed for travelers who want to hit the slopes, climb mountains, or participate in other “risky” behavior. While adventure and sports policies usually cost more than traditional policies, they provide additional medical insurance in case of injury. Before buying, be sure to read the fine print to ensure your activities are covered.
  • Group Policies: For groups of 10 or more, Squaremouth also offers group policies that will cover everyone on an itinerary. While they usually include all the benefits of a single trip plan, groups can often get discounts by booking together under a single policy.

What Additional Insurance Options are Available?

Although most travel insurance plans will cover the most common situations, buying insurance early can unlock additional benefits. When purchasing a plan within 14 to 21 days of placing the first deposit on your trip, many policies allow you to add cancel for any reason coverage or pre-existing condition waivers.

  • Cancel for Any Reason Coverage: Trip cancellation coverage allows travelers to recover their costs if a covered situation forces them to cancel their trip, such as an illness, death of a family member, or a storm at their destination. Cancel for any reason coverage allows policy holders to recover between 50% and 70% of their costs if they decide not to take a trip for a situation not covered by trip cancellation.
  • Pre-Existing Condition Waivers: Most travel insurance policies may not cover recurrences of conditions individuals already have, such as heart disease or cancers. Buying travel insurance early may grant access to pre-existing condition waivers, which will extend trip cancellation and health benefits to a recurrence of a pre-existing condition diagnosed or required care 120 days or more before your trip.

How to Buy Travel Insurance from Squaremouth


Searching for travel insurance on Squaremouth.com begins with their three-step quote process. To start searching, you will be asked to provide details about your trip, including:

  1. Your departure date, return date, and primary destination.
  1. Your age, country of residence and citizenship, and ages of travelers on the trip.
  1. Your date of first deposit, if you plan on including cancellation insurance, total amount of your trip and if any payments are remaining.

From there, Squaremouth.com will show you a number of policies that may fit your requirements. You can also break down options by their benefits, including:

  • Trip interruption
  • Emergency medical
  • Medical evacuation
  • Pre-existing medical condition waivers
  • Cancel for any reason insurance
  • Primary medical coverage

You can also search by top selling plans, insurance companies, and plan prices. Once you have decided upon a plan, you will be asked additional questions about the travelers on your plan, including:

  • Your name, birthdate and gender
  • The names, birthdates and gender of everyone on your itinerary
  • Home address and e-mail
  • Telephone number

Payments are handled online through a major credit card or debit card.

How Do I Get my Travel Insurance Documents?

Once your payment is confirmed by Squaremouth, your receipt and documents will be delivered to you via email. For policies purchased from Tin Leg, your insurance documents will come directly from Squaremouth.

Policies purchased from any other travel insurance provider will arrive via e-mail from the companies themselves. It’s important to retain this information, as it will provide not only proof of insurance, but also give you the addresses and phone numbers of the plan’s customer service and claims teams.


Transactions on Squaremouth are secured by a RSA 2048-bit encryption. Amazon Web Services provides the SSL certificate for the website, and is renewed yearly.

Squaremouth Reviews and Ratings

Of all the travel insurance markets, Squaremouth may offer not only the most reviews of products, but offers a number of reviews of their service as well. Travelers are encouraged to leave both good and bad reviews of their insurance companies, based on their customer service and claims experiences.

Over the years, Squaremouth earned a Stevie Award for having a top-tier customer service department, alongside Travel Weekly Magellan Awards and Best of the Biz awards. Squaremouth is also the preferred travel insurance provider for Forbes.com.

Outside of their awards, the company has mixed reviews. The company is rated D- by the Better Business Bureau, and is not accredited by the independent organization. TrustPilot gives Squaremouth an average review of just under three stars, and Angie’s List gives them a B rating based on one review.

As with any travel insurance market, it’s important to do your research to determine if you feel comfortable with a company before buying. Although there are mixed reviews, Squaremouth is a reputable company offering travel insurance policies from multiple providers.

Pros and Cons of Squaremouth


  • One of the biggest travel insurance marketplaces online
  • Multiple levels of coverage, ranging from single trip plans to annual, multi-trip, and adventure plans
  • Over 30 insurance providers and 90 plans in one place


  • Selection of multiple insurance plans may be overwhelming
  • Mixed reviews from BBB and others
  • Company can only advocate on behalf of customers, but can’t overturn claim decisions

Final Thoughts on Squaremouth

Overall, Squaremouth is possibly the most comprehensive travel insurance marketplace available today. With over 90 policies available from 32 insurance companies (including their own brand), the site is one of the first places people shop for their insurance. But with so many choices, smart shoppers should approach the site with a knowledge of what benefits they want, and which companies have the best reviews in the event a claim is necessary.

Frequently Asked Questions

Is Squaremouth Trustworthy?

Squaremouth is one of the oldest travel insurance marketplaces on the internet, with a wide selection of insurance companies and plans represented.

Who owns Squaremouth?

Squaremouth is founded and co-owned by company CEO Chris Harvey. Based in Florida, Squaremouth is an independent corporation that has made the Inc. 5000 list every year between 2013 and 2020.

What is Squaremouth?

Squaremouth is one of many travel insurance marketplace websites available to travelers based in the U.S. and other parts of the world. The company sells their own brand of travel insurance, Tin Leg, along with plans from 31 other insurance companies.

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