Cliff Insurance Agency, Inc is a next generation insurance provider, serving the needs of businesses and individuals in Madison, WI, Middleton, WI and the surrounding area. When you need auto insurance, homeowners insurance, renters insurance, motorcycle insurance, business insurance, and many others, we find the most competitively priced solutions for you.

Since 1956, we’ve provided trusted advice and insurance options from a wide variety of popular carriers such as Progressive Insurance and Allstate. Our unwavering commitment to serve you with the utmost integrity make us the simple choice for all of your insurance needs.

At Cliff Insurance Agency, Inc, each client is treated as a unique case. Our approach to finding the best coverage for you is never ‘cookie-cutter’. You can expect the absolute best from us whether you are looking for help with auto insurance or any of the other lines you see on our website. We have grown 300% in nine years as a result of our expertise and personalized approach. Referrals from happy clients drive our growth. We choose from a wide menu of options to ensure you have the best coverage for the best price.

At Cliff Insurance Agency, Inc, your phone calls will be answered by a real, live person during our business hours—no phone system, no scripts, just a friendly staff prepared to answer all of your insurance questions. See what a difference great solutions and superior service can make! We’re here to help. – Dennis Cliff

Preventing Package Theft

Posted: December 16, 2024

If you do a lot of online shopping during the holiday or year-round, be aware of the growing threat of package theft. Package thieves, also known as “porch pirates,” have become so brazen that some will even tail delivery drivers to swoop up packages the minute they are gone. In a recent year, over 260 million packages were stolen across the U.S., costing consumers millions...

Safety Tips for Online Shopping

Posted: December 1, 2024

It is that time of year again. Whatever holiday you celebrate, Americans nationwide go to their favorite online retailers to buy holiday decorations, party supplies, and gifts to make the season merry and bright. The convenience of the internet is hard to resist, but the freedom and flexibility of online buying come with some grave risks. Cybercrime is on the rise. In a recent year,...

Driving Safety Tips as Daylight Savings Ends

Posted: November 16, 2024

Fall and the end of daylight savings time is upon us once again. As the clocks are turned back an hour, you can expect your normal sleeping patterns to be disrupted for about a week before they return to normal, as the amount of sunlight in a day is less. Driving to work or around town could be just that much more challenging. Here are some...

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Preventing Package Theft

Safety Tips for Online Shopping

Driving Safety Tips as Daylight Savings Ends