• Travel Insurance Quote

    What is single trip travel insurance?

    Single Trip Travel Insurance is ideal if you are taking a single trip of any length. It can include coverage for medical, evacuation and cancellation, among other benefits.


  • Travel Insurance Quote

    What is annual travel insurance?

    Annual Travel Insurance is good for frequent travelers planning multiple trips throughout a year. It can include coverage for medical, evacuation and cancellation, among other benefits.

  • Group Travel Insurance Quote

    What is group travel insurance?

    Group travel insurance allows parties of 10 or more to purchase one travel insurance policy at a group rate. This can be a more convenient and economical option for organized groups traveling together to the same destination. All travelers must be U.S. citizens.

    Group travel insurance offers the same benefits as single trip policies, including cancellation, medical and medical evacuation, travel delay, and lost and delayed baggage.

    Start Group Quote

Squaremouth Featured on Television

Fox News Tampa Bay aired a section on Squaremouth's unique company culture in April 2012.

See what happened

Squaremouth's Reseller Rating

Safe with our Zero Complaint Guarantee

Every travel insurance policy purchased through Squaremouth comes with the Zero Complaint Guarantee.

In the event of a complaint, Squaremouth will mediate with the insurance provider on behalf of our client.

Unless the complaint is resolved to Squaremouth's satisfaction, the provider will be removed from the website.

Read more

One of Florida’s Best Companies to Work For in 2015

Headquartered in St. Petersburg, Florida, Squaremouth’s unique work environment and core values have led to consistent recognition for company culture, outstanding office space and rapid growth.

In 2015, Florida Trend magazine named Squaremouth the 18th best small company to work for in Florida, highlighting the company’s exceptional culture in a special feature article.

Read More