Flynn Insurance Agency
An independent insurance agent located in Boston, MA. We offer many types of Insurance. Coverage cannot be bound via social media.
To make changes to your policy, you must talk to an agent. The Flynn Insurance Agency is a family-owned and operated business located in the historic City Square section of Charlestown in Boston, Massachusetts. We have been providing insurance and employee benefits solutions to our customers throughout the New England area for more than 30 years. Specializing in individual insurance, voluntary employee benefits, and commercial insurance products, we work with the highest caliber insurance carriers and partners to provide our customers with the proper risk strategy to protect themselves, their families, their businesses, and their employees. As an independent insurance agency, we have access to the highest-rated carriers in the industry and can provide you with competitive pricing, top-tier products, enhanced coverage, various discounts, and superior customer service.
09/10/2026
💡 "I Thought I Was Covered…" 💸
This is the most expensive phrase in insurance. Thinking your policy does something that it doesn’t leads to gaps that could cost you much more than you think.
But we don’t expect you to be an insurance expert. That’s why we try to make sure your policies match your life at least once a year. We try to avoid things like:
🚫 Sewer backup not included
🏠 Business equipment stored at home
🏚️ Out-of-date replacement cost on your home
🚗 Liability only with a valuable vehicle
If you haven’t had a review in a while, get in touch with us. We can help you find these issues before they become “I thought…” moments. 🛡️
09/08/2026
🚗 3 Business Auto Tips 💼
Running a business with vehicles? These gaps can cost you. 🛡️
1️⃣ Personal Auto ≠ Business Use: Employees' personal policies deny business claims. HNOA (Hired & Non-Owned Auto) protects your business from liability when employees use personal cars for work. ☕
2️⃣ Company Vehicles Need Full Coverage: Comprehensive + collision + commercial-specific coverage. Don't skip this. 🚐
3️⃣ Rideshare or Delivery? New Rules: Uber, DoorDash, and deliveries are usually excluded in both personal and commercial policies. You may need separate coverage. 📱
Small gap = big problem. Let's talk. Questions? DM us. 📩
09/04/2026
🚙 Buying a Car? 3 Reasons to Chat With Me First 🚗
Before you sign the paperwork, here's why a quick call matters:
1️⃣ Coverage Needs Change: Upgrading to something nicer? Financed cars require comprehensive and collision coverage. Liability-only leaves you exposed. 💰
2️⃣ Rates Vary By Model. That dream car might cost way more to insure. A quick call saves you insurance sticker shock. 📊
3️⃣ Bundling Saves Money: Timing matters. Bundle with home or add to existing policies, and you save moolah. 💸
New car shopping is fun. New car insurance, well, not as much. But that’s why we’re here.
Ready to talk? Give us a call. 📞
09/03/2026
🗣️ Ask an Agent: 3 Common Questions 🛡️
We hear all kinds of questions as insurance agents. Answering these questions is part of our job, and honestly, one that we don’t mind. Insurance isn’t always easy to grasp, and helping people understand it a little better is incredibly rewarding. 🤝
That’s why we’ve listed three questions we get asked a lot right here to save you the trouble of asking:
1️⃣ Why do I need all of this coverage?
Your coverage amount should match the cost to replace the items on the policy. That said, every situation is different, and costs change over time, so go over your policy with us to make sure everything is right. 📋
2️⃣ Why did my rate change?
Rates can shift due to claims history, driving record, inflation, or market changes. I can guarantee that it is not because your agent raised your rates! 📈
3️⃣ Does bundling actually help?
Almost always. It can make things easier when dealing with your company, streamline service, and give you a discount on both policies. 💡
If you have a question that isn’t listed, or want to know more about one of these three, raise your hand in the comments or send us a DM! 🙋♂️💬
09/02/2026
Back to School time! It’s been a long summer, and it’s time to get back to class and crack those books. We send our best wishes out to all of our scholars this year, including those starting out at a new school or maybe gearing up for graduation.
09/01/2026
A record number of U.S. adults under 35 are living with their parents, according to a recent Realtor.com study.
In 2025, 25.2 million adults under 35 lived at home, a higher share than during the COVID-19 pandemic.
Many are working, but wages are not always keeping up with the cost of living. Among adults ages 25 to 34 who live at home, roughly 7 in 10 have jobs.
Housing affordability is a major factor. Higher home prices, elevated mortgage rates, rent, student loan payments, car payments, and everyday expenses can make living independently harder to sustain.
For some families, moving back home may be a way to reduce expenses, rebuild savings, or create more breathing room before taking the next step.
The broader takeaway is that financial independence does not always follow a straight timeline. Cost-of-living pressures are reshaping what adulthood, housing, and household decisions look like for many families.
Source:
Record number of U.S. adults are moving in with their parents as costs rise, study finds One woman in her mid-30s said her $60,000 annual income wasn't enough to cover all her bills after a breakup, leading her to move back home.
09/01/2026
Let the ’ber months begin! 🍂☕
Hello, September! Cooler mornings, changing leaves, football, apple picking, pumpkin everything… we’re ready for you.
The start of the ’ber months also means a new season is right around the corner. As life changes, it’s always a good time to make sure your insurance is keeping up with it.
Here’s to a happy, cozy & well-covered September! 🧡
08/31/2026
For many homeowners, the biggest weather risk may no longer be hurricanes.
New research from First Street found that severe convective storms, including tornadoes, hail, and damaging winds, have become the costliest insured natural disasters worldwide.
In 2025, these storms accounted for one-third of global natural disaster economic losses. Insured and uninsured losses totaled $82 billion, with $68 billion concentrated in the U.S.
Hail is the biggest driver of insurance payouts within this category, followed by severe winds.
These storms tend to move quickly, but they can cause widespread damage to homes, cars, businesses, and infrastructure.
For homeowners, the growing cost of severe weather can show up in more than repairs. It may also affect insurance premiums, property maintenance, emergency savings, and long-term housing costs.
As weather risks shift, it can be worth reviewing coverage, deductibles, and how prepared your household is for unexpected property damage.
Source:
The biggest weather risk for homeowners? It's no longer hurricanes. Severe "convective" storms account for roughly a third of global natural disaster economic losses, a new study finds.
08/29/2026
Back-to-school season is bringing higher costs for many families.
A new analysis found that a typical basket of school items, including notebooks, lunch boxes, and index cards, is up nearly 8% compared with last year.
School lunches are also more expensive, with the cost of a typical packed lunch up 11%.
The analysis estimates families may spend roughly $4,000 per student on school supplies and lunches this year, including about $175 on school items and $3,800 on packed lunches.
Some items have seen especially sharp increases. Lunch boxes are up 27%, one-subject notebooks are up 23%, and index cards are up 22%.
Higher tariffs, imported school supplies, food prices, and energy costs are all contributing to the increase.
For families, back-to-school shopping is a reminder that seasonal expenses can add up quickly, especially when everyday costs are already stretching household budgets.
Source:
Families face higher costs as back-to-school season nears U.S. households will spend roughly $4,000 per student on school supplies and lunches this year, a new analysis found.
07/31/2026
Facebook Marketplace meetups: It’s all smooth until the keys change hands—coverage matters more than most people think.
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Contact the business
Website
Address
30 Park Street, Suite 2
Boston, MA
02129
Opening Hours
| Monday | 9am - 5pm |
| Tuesday | 9am - 5pm |
| Wednesday | 9am - 5pm |
| Thursday | 9am - 5pm |
| Friday | 9am - 5pm |