Dairyland Insurance

Dairyland Insurance is one of the companies that we shop for you when you submit your information in our online quote system. Our system quickly collects the best rates for you and will allow you to choose the best, cheapest, and fastest FR44 Florida Insurance. Our agents are bilingual, speaking both Spanish and English, and are available to assist you with your Insurance needs.

About Dairyland Insurance – A History of Helping High-Risk Drivers

Dairyland Insurance was founded in Wisconsin in 1953, built on the idea that all drivers — even those with imperfect records — deserve access to reliable, affordable insurance. From the start, the company focused on serving non-standard or high-risk drivers, offering real coverage to people who didn’t always qualify for traditional insurance.

In 1966, Dairyland became part of Sentry Insurance, a financially strong company that has been protecting drivers and businesses since 1916. Sentry holds an A+ rating from AM Best, a trusted indicator of long-term financial stability and claims-paying ability.

Today, Dairyland remains focused on what it does best:

• Helping drivers with past tickets, DUIs, or lapses in coverage
• Supporting flexible policies for non-owner and motorcycle coverage
• Offering real-world payment plans that meet people where they are

With over 60 years of experience and coverage offered in more than 35 states, Dairyland continues to provide dependable service for drivers who need a second chance — including Florida drivers who require an FR44 filing.