Mon–Fri 8am–5pm · Sat 9am–1pm · Sarasota, FLRicky727-748-1701Lizzy · Receptionist 24/7941-260-0177info@riskyrickyinsurance.com
¿Prefieres español? Ver esta página en español →
Commercial Insurance

Small Fleet Insurance for Florida Operators

Once you're past two or three vehicles, insuring each one separately gets expensive and messy. A fleet policy puts every unit, driver and trailer under one schedule — and Ricardo is the one person tracking it.

Fleet programs are typically available starting at a handful of vehicles and scale up from there. They're rated on the operation as a whole: the kind of work, the drivers, the radius, loss history and how the vehicles are maintained. Done right, you get consistent limits across every unit, one renewal date, and the ability to add or remove vehicles mid-term without starting over.

Ricardo works with small transportation companies, contractors running multiple crews and service businesses with a route to cover. He speaks the language of DOT numbers, MC authority, driver files and schedules — and, literally, Spanish.

Who this is for

  • Local and regional carriers with 2–25 power units
  • Contractors running several crew trucks and trailers
  • Delivery, courier and last-mile operators
  • Landscaping, cleaning and property-service companies
  • Businesses adding vehicles faster than their current agent can keep up

What this coverage typically addresses

Scheduled auto liability

One liability limit that applies across every scheduled vehicle so your certificates look the same to every customer.

Physical damage by unit

Collision and comprehensive can be set per vehicle, so an older trailer isn't rated like a new tractor.

Hired & non-owned

Covers the rental you grabbed for a busy week and the employee who ran parts in their own car.

Motor truck cargo

For operators hauling for hire. Limits depend on what you carry and what your shippers require.

Trailer interchange

If you pull trailers you don't own under an interchange agreement.

Filings

Where your operation requires state or federal filings, Ricardo coordinates them with the carrier.

What Ricardo will ask you for

Have these ready and the quote goes smoother. Don't have everything? Call anyway — Ricardo will tell you what actually matters for your situation.

  • Vehicle schedule: year, make, model, GVW and VIN for each unit
  • Driver list with license numbers, DOB and years of CDL/experience
  • DOT and MC numbers if you have authority
  • Commodities hauled and typical radius
  • Loss runs (3–5 years) from your current carrier
  • Current premium and renewal date

Built for the owner who's also the dispatcher

Most fleet owners under 25 units don't have a safety manager or an insurance department. They have a phone and a whiteboard. Ricardo's job is to be the person who already knows your schedule when you call to add a truck, swap a driver or send a certificate to a new broker.

He'll also tell you, before renewal, what underwriters are going to flag — a driver with a recent violation, a unit that should come off the schedule, a radius that's drifted — so the renewal isn't a surprise.

Common questions

How many vehicles do I need for a fleet policy?

Programs vary by carrier. Some start at two or three units; others prefer five or more. Ricardo will tell you which approach fits your size and whether individual commercial auto policies make more sense for now.

Can I add a vehicle in the middle of the policy?

Yes. Scheduled fleet policies are built for that. Send Ricardo the VIN and intended use and he'll submit the endorsement to the carrier. Timing depends on the carrier.

Do you handle DOT or state filings?

Where a carrier offers the filing, Ricardo coordinates it. If you're new to authority, he'll walk you through what your operation actually needs.

What if one driver has a bad record?

It depends on the violation and the carrier. Sometimes a driver can be excluded or placed in a different role. Ricardo will tell you honestly what the options are rather than letting it blow up at renewal.

Is Spanish-language service available for the whole account?

Yes — applications, driver questions, certificates and claims guidance can all be handled in Spanish.

Coverage availability, eligibility and pricing vary by carrier and are subject to underwriting. Nothing on this page guarantees a premium, savings, approval or coverage.

Related coverage

Commercial Auto

Trucks, vans, pickups and work vehicles. Liability, physical damage, cargo and the filings your operation may need.

Learn more →

Contractors / General Liability

General liability for GCs, subs and trades. Certificates handled by someone who's been on the job site.

Learn more →

Commercial Marine

Charter, guide, dive, towing and workboat operations. Hull, P&I and the certificates your dock or port requires.

Learn more →
Small Fleet

Start your quote

Answer a few questions and Ricardo gets your details instantly. Takes about two minutes. Prefer to talk? Call 727-748-1701 (Ricky direct · business hours).

Life's risky. Coverage shouldn't be.

Call Ricardo. Get options, not a runaround.

Personal service from Ricardo, backed by 24/7 bilingual assistance. Call for a quote or send the basics by email and Ricardo will take it from there.

Call Rickybusiness hoursLizzy 24/7always openTextGet a Quote