Insurance Insights

Insights

Expert Advice for Life’s Complexities

Stay informed with guidance from our advisory team, designed for clients with unique lifestyles, evolving coverage needs, and high-value assets, helping you protect what matters most with confidence.

Is High-Net-Worth Home Insurance Worth the Higher Premium? A Real Claims Story

By Kristin Bailey | September 30, 2026

A Bailey Howes client’s real high-value home claim with PURE shows what sets specialty coverage apart—and what it’s worth beyond the premium.

Beyond the Policy: Why Insurance Advocacy Matters for Growing Portfolios

By Greg Howes | August 31, 2026

Standard insurance plans are not designed to address the complexities of wealth management. Learn how strategic advocacy helps ensure your insurance keeps pace.

Protect Your Wealth: Choosing the Right Amount of Liability Insurance

By Greg Howes | July 22, 2026

How much liability insurance you need often changes as your life evolves and your assets grow. Learn how umbrella insurance can help protect you as you build wealth.

Addressing Risks in Household Employment: Why Every Family Needs Nanny Insurance

By Kristin Bailey | June 25, 2026

When you hire a nanny or other domestic employee, your household is exposed to new types of risks. Learn what these risks are and how to address them.

Fine Art Insurance: Risks Serious Collectors Should Consider

By Greg Howes | May 20, 2026

For many of the families we advise, fine art is not simply an asset. It is part of a legacy. Whether your collection was carefully curated over time or entrusted through an inheritance, you have acquired a responsibility that goes beyond protecting each piece’s value—you are preserving something that cannot be replaced.

Know Your Flood Risk (Even if You’re Not in a Flood Zone)

By Greg Howes | April 27, 2026

Flood insurance is often overlooked as an essential part of a risk management plan, leaving many of the families we work with—and the assets, investments, and plans they’ve built over a lifetime—unintentionally exposed to financial risk. Discover your home’s risk level and secure Flood Insurance in Massachusetts today.

Hear From Our Clients

What Makes the Bailey Howes Insurance Experience Different?

    
 
 
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   Lee-Ann Norman 
 8 September 2025
 
 
 Trustindex verifies that the original source of the review is Google. Catherine Washington is excellent to work with!  She has helped me with my personal insurance questions as well as preparing to open a business questions.
  
 
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   Anders Beer 
 26 August 2025
 
 
 Trustindex verifies that the original source of the review is Google. I have had nothing but good experiences with Howes insurance group. Greg Howes, Traci Madigan, and Mike Umano were all really responsive and articulate when it came to finding the right insurance and answering questions regarding home, umbrella, and auto policies.

I have had plenty of questions for all of the people I named, and every one of them has been really insightful and articulate. Most recently I asked about those consumer insurance policies that are often sold by retailers and what differentiates them from the coverage under our homeowners policy. Mike was kind enough to go into detail about it and I really appreciated his objective breakdown on how the coverage works.

Keep up the fine work, Howes Insurance Group :)
  
 
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   Robert Stemple 
 18 August 2025
 
 
 Trustindex verifies that the original source of the review is Google. Over 30 years of helpful, quick answers. They treat you as friends not customers😀👍👍👍
  
 
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   Roger Beatty 
 4 December 2024
 
 
 Trustindex verifies that the original source of the review is Google. Howes is a small agency staffed with highly knowledgeable insurance professionals -- they're large enough to attract and retain experienced pros, and small enough to ensure personal contact in all business interactions. No voice mail maze, no call center, no chatbots -- they'll answer the phone directly, or call you back same day. When I call, I usually reach somebody I already know on my first attempt. I've been with them for years, and they've always done a great job.
  
 
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   Irwin Hipsman 
 26 November 2024
 
 
 Trustindex verifies that the original source of the review is Google. We have both our home and auto with Howes Insurance. Recently, we had a very challenging purchase of an auto and damage to our house. In both situations they were incredibly helpful and reassuring. Highly recommend the team and a special shout out to Traci.
  
 
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   Gregory Ladd 
 30 October 2024
 
 
 Trustindex verifies that the original source of the review is Google. The personalized service and breath of offerings really makes a difference!
  
 
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   Steve Neff 
 3 October 2024
 
 
 Trustindex verifies that the original source of the review is Google. The Howes team has been a valued services and support team. They are knowledgeable, proactive and we have a comprehensive umbrella policy for multiple properties, cars etc. Also a big shout out to our Account Manager Jennifer Drasser.
  
 
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   Jack 
 23 September 2024
 
 
 Trustindex verifies that the original source of the review is Google. From the moment I placed a call to Greg Howes, I knew I was in good hands. He took the time to explain every detail of the half dozen properties and autos I wanted to insure and came in less than other quotes at a higher level of coverage! Jennifer continued the process with countless phone conversations and emails. She's knowledgeable, patient, helpful, empathetic, experienced and extremely affable. I can't say enough and am grateful to have found Howes Insurance Group. You will be too!
  
 
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   Sylvia Diaz 
 6 September 2024
 
 
 Trustindex verifies that the original source of the review is Google. It's' a comfort for me to know that I have The Howe's Insurance Group behind me to help me navigate the complex business of insurance.

The Howe's Insurance Group is very responsive to my questions and needs. Together, we review, my family's insurance needs every year.