Commercial insurance
Protect the Business You've Built
Comprehensive commercial coverage for businesses of every size across Florida, Michigan, Texas, and Missouri — from startups to established enterprises.
Get a Business QuoteCommercial Coverage Options
From a single-employee shop to a multi-location operation, we have the right coverage for your business.
Business Owner Policy (BOP)
A bundled policy combining general liability and commercial property coverage — the smart, cost-effective foundation for most small to mid-size businesses.
- General liability protection
- Commercial property coverage
- Business interruption insurance
- Customizable add-ons
General Liability
Protect your business from third-party claims of bodily injury, property damage, and personal injury. Essential coverage for any customer-facing operation.
- Bodily injury claims
- Property damage liability
- Personal & advertising injury
- Legal defense costs
Commercial Auto
Coverage for vehicles used in your business operations — from a single work truck to an entire fleet. We serve businesses across Florida, Michigan, Texas, and Missouri.
- Liability for business vehicles
- Collision & comprehensive
- Hired & non-owned auto
- Fleet discounts available
Workers' Compensation
Required for most employers, workers' comp covers medical expenses and lost wages for employees injured on the job — protecting both your team and your business. We handle compliance across all states we serve.
- Medical expense coverage
- Lost wage replacement
- Multi-state compliance
- Employer liability protection
Trucking Insurance
Specialized coverage for owner-operators, small fleets, and freight carriers operating across Florida, Michigan, Texas, Missouri, and beyond. We understand the unique risks of the trucking industry and find policies that keep you moving.
- Primary liability coverage
- Physical damage & cargo
- Owner-operator policies
- Fleet & non-trucking liability
Keeping Florida's Truckers Protected on Every Mile
Whether you're an owner-operator running a single rig or managing a growing fleet, we specialize in trucking insurance that meets FMCSA requirements and protects your livelihood. We work with carriers who understand the road.
- Primary liability (up to $1M+)
- Physical damage coverage
- Motor truck cargo insurance
- Non-trucking liability
- Bobtail insurance
- FMCSA filing (Form MCS-90)
Owner-Operators
You own your rig and your livelihood. We find policies that protect both — whether you're leased to a carrier or running under your own authority.
Small Fleets
Managing 2–20 trucks? We bundle coverage across your fleet to simplify your policy and reduce your premiums.
Freight & Cargo Carriers
Cargo damage claims can be costly. Motor truck cargo coverage protects the goods you haul from pickup to delivery.
Industries We Serve
We work with businesses across Florida in a wide range of industries.
Why Businesses Across 4 States Trust Windward
Multi-State Business Expertise
We're licensed in Florida, Michigan, Texas, and Missouri — and we understand the unique risks, regulations, and compliance requirements businesses face in each state.
Carrier Access
We work with dozens of top-rated commercial carriers to find the right fit for your industry, size, and risk profile.
Compliance Guidance
Each state has specific insurance requirements for businesses. We make sure you're covered and compliant from day one, wherever you operate.
Request Your Free Business Insurance Quote
Tell us about your business and a licensed commercial agent will be in touch within one business day.
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