85+ A-rated carriers shopping your rate. 1,400+ active policies. Bilingual EN/ES. Free quotes in 2 hours. Hard-to-place welcome — accidents, violations, new MC, international licenses.
San Pedro is the gateway community to the Port of Los Angeles, and a large share of its working residents are tied to the harbor — including the owner-operators and small fleets that move containers off the docks. Port drayage out of San Pedro means running interchange containers and pool chassis you do not own, which requires trailer interchange coverage and UIIA-compliant insurance limits that standard trucking policies leave out. Checkers Truck Insurance Services has been writing port drayage and intermodal policies for San Pedro and the wider LA Harbor area since 2009, with bilingual English and Spanish service throughout.
We currently maintain over 1,400 active policies across the Inland Empire and Greater Los Angeles, hold a 4.9/5 rating from 127+ trucker reviews, and shop 85+ A-rated carriers for every quote — including Progressive, Great American, Berkshire Hathaway GUARD, CNA, Lloyd's of London, Cover Whale, and AmTrust.
Independent broker. San Pedro-area expertise. Real underwriting relationships.
Established 2009. We know how San Pedro risks underwrite, what carriers want, and how to get you priced.
Progressive, Great American, Berkshire Hathaway GUARD, CNA, Lloyd's, Cover Whale, AmTrust — we shop them all.
Quote, bind, claims, renewals — all in English or Spanish. Hablamos tu idioma.
Standard accounts quoted within 2 business hours. Same-day binding once paperwork clears.
Every line a working trucker actually needs — packaged for owner-operators through fleets.
Primary liability up to $1M+. Required by FMCSA for interstate commerce.
Protects the freight you're hauling. Customizable limits for dry van, reefer, flatbed, and high-value loads.
Covers your tractor and trailer for collision, theft, fire, and weather damage.
Premises and operations coverage — required by most shippers and brokers.
Covers non-owned trailers you pull under interchange agreement.
Bobtail coverage for when you're operating off-dispatch.
Most brokers can't write you. We can — because hard-to-place is what we do.
We have surplus-lines markets — including Lloyd's of London syndicates and specialty carriers like Cover Whale — that exist specifically to write port drayage, dry van, refrigerated, last-mile delivery, and intermodal operations that standard markets won't touch. We package your submission so underwriters see the full story, not just the loss runs.
Fill the form. A San Pedro-area specialist calls you back within 2 hours with rates from 85+ carriers.
Free. No obligation. Bilingual agents available.
San Pedro port drayage operators typically pay $14,000-$22,000 per year in 2026 for a single tractor with clean records. Trailer interchange and UIIA-compliant coverage required for Port of LA access drives the cost above standard dry van rates. Call (909) 824-6500 for an exact quote.
Yes. Drayage is one of our most common placements. We have multiple A-rated carriers with strong appetite for ports of LA/Long Beach drayage out of the LA Harbor area, including operations with prior claims or a brand-new MC number.
Yes. International licenses are part of our hard-to-place specialty. We have surplus-lines markets that will write drivers operating on international, Mexican, or recently transferred US licenses, with the right documentation packaged correctly.
Sí. Our entire team is bilingual English/Spanish. Quotes, binding, claims, renewals — all available in either language. Hablamos español. Llame al (909) 824-6500.
Standard San Pedro accounts get quoted within 2 business hours. Hard-to-place accounts take 24–48 hours due to surplus-lines underwriting. Same-day binding once paperwork and down payment clear.
Click to see rates in your city.
Join 1,400+ truckers across the Inland Empire who trust Checkers.
Get Free Quote →🇲🇽 Hablamos español — llame al (909) 824-6500 para una cotización gratis.