Services About Approach Contact (617) 310-8200

Boston, Massachusetts

Welcome to Gemini Transportation Underwriters —
where your fleet's protection begins with a conversation that actually understands it.

We underwrite transportation insurance the way we'd want our own business insured: carefully, thoroughly, and with someone who picks up the phone.

Schedule a Consultation Explore Our Services
15+ Years of underwriting experience
Nationwide License & compliance support
Direct Access to underwriters, not call centers
Boston skyline viewed from the waterfront, representing Gemini Transportation Underwriters' home base

What We Do

Comprehensive transportation
insurance solutions

01

Commercial Auto Insurance

From single trucks to multi-vehicle fleets, we structure policies that cover what matters — physical damage, liability, cargo, and the gaps in between.

02

Cargo & Freight Insurance

Protect your freight from dock to door. We negotiate terms that reflect the real value of what you haul — not the minimum the market will accept.

03

UCR & DOT Compliance

Unified Carrier Registration, operating authority, and all the paperwork that keeps you legal on the road. We handle the details so you don't have to.

04

General Liability

Whether you're a broker, carrier, or logistics provider, we structure general liability coverage that matches the scope and risk of your operations.

05

Risk Management Consulting

Better insurance starts with better risk practices. We review your operations and recommend changes that lower your exposure and your premiums.

06

Claims Advocacy

When something goes wrong, we're in your corner. We help prepare, file, and pursue claims so you get the resolution you're entitled to — not the first offer on the table.

Professional office setting representing Gemini Transportation Underwriters
Team consultation at Gemini Transportation Underwriters

About Us

Built on relationships,
not transactions

Gemini Transportation Underwriters was founded on a simple observation: the transportation industry deserves insurance partners who actually understand it. Not generalists who treat a trucking company the same as a retail shop.

Based in the heart of Boston at 99 Summer Street, we serve transportation companies across the country — from owner-operators building their first fleet to national carriers managing complex risk portfolios. Our team brings decades of combined experience in transportation underwriting, claims, and compliance.

We don't sell policies and walk away. We stay engaged because we know that the right coverage isn't a one-time decision — it's an ongoing conversation that evolves with your business.

Our Principle Every client gets direct access to their underwriter. No runaround.
Our Approach We shop multiple markets to find terms that actually fit your operation.
Our Standard If we wouldn't accept the terms ourselves, we won't offer them to you.

How We Work

A process that respects
your time

01

Discovery Call

We start with a conversation — not a form. Tell us about your fleet, your routes, your concerns. We listen before we recommend anything.

02

Market Analysis

We review your current coverage, analyze your risk profile, and identify gaps. Then we present options from multiple carriers — not just one.

03

Placement & Documentation

Once you choose a direction, we handle the paperwork, filings, and compliance requirements. You get clear documentation you can actually read.

04

Ongoing Partnership

Insurance isn't set-and-forget. We review your policy annually, adjust for changes, and are available whenever something comes up.

Gemini understood our business from the first call. They didn't try to sell us the most expensive policy — they sold us the right one. That's the difference between an insurance agent and an insurance partner.

— A transportation company we've worked with for five years

Get in Touch

Let's talk about
your coverage

Whether you're looking to switch carriers, renew your policy, or just get a second opinion on your current coverage, we're here to help. Reach out by phone, email, or stop by our office.

Office 99 Summer St
Boston, MA 02110
Hours Mon – Fri: 9:00 AM – 5:30 PM EST
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