Updated September 2026
Best Owner-Operator Companies in Cutler Bay, Florida (September 2026)
Through September 2026, 550 carriers in Cutler Bay, Florida contract owner-operators across the lanes Lanefinder tracks. RAY'S TRANSPORT INC leads with an average gross weekly revenue of $8,500 and an average $2,000 sign-on bonus. WINNERS TRANSPORTATION LLC follows at $2,657/week gross. Florida trucking runs on I-95 / I-75 north-south spines and the I-4 Tampa-Orlando-Daytona cross, with Port of Miami and Port of Jacksonville as major gateways alongside heavy citrus and produce agriculture freight.
What changed in September 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Where Cutler Bay, Florida differs from the Florida baseline
| Cutler Bay, Florida | Florida top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,742 | $5,326 | +27% |
| Dedicated routes | 47% | 35% | +12 pt |
| Pet-friendly fleets | 88% | 82% | +6 pt |
| Riders-allowed policies | 90% | 84% | +6 pt |
Source: Lanefinder index, September 2026
The largest gap is on average weekly pay: Cutler Bay, Florida sits 27% above the Florida baseline.
The owner-operator carriers leading Cutler Bay, Florida this month
The top of the list is RAY'S TRANSPORT INC at $8,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1RAY'S TRANSPORT INC — $8,500/wk
RAY'S TRANSPORT INC tops the Cutler Bay, Florida ranking with the strongest composite score across pay, safety, benefits, and operational signals. RAY'S TRANSPORT INC pays above the 89th percentile on gross weekly revenue for the Cutler Bay, Florida market. RAY'S TRANSPORT INC's top FMCSA dimension is driver fitness, in the 87th percentile. RAY'S TRANSPORT INC responds to driver applications more reliably than the Cutler Bay, Florida median.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC ranks in the 92nd percentile for driver fitness on FMCSA SAFER data. WINNERS TRANSPORTATION LLC tracks as a responsive employer on application-response data.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC ranks in the 96th percentile for hours-of-service compliance on FMCSA SAFER data. Application-response data flags this carrier as a responsive employer.
Also in the top 10: #4 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #5 WIDER GROUP INC at $6,250/wk, #6 Freight X LLC at $6,000/wk, #7 BLUE LIGHTNING LOGISTICS at $7,000/wk, #8 Ali Star Inc at $10,000/wk, #9 KILO METER LOGISTIC INC at $7,500/wk, #10 COMMONWEALTH TRANSPORTATION LLC at $4,366/wk.
What Cutler Bay, Florida drivers actually run
8% of Cutler Bay, Florida's active CDL postings are regional and 91% are OTR; local plus semi-local accounts for the rest (1%).
Across Cutler Bay, Florida CDL postings: 2% with guaranteed pay, 28% dedicated, 91% take-truck-home, 72% pet-friendly, 69% riders-allowed.
Driving CDL in Florida
Florida CDL work splits cleanly between coastal port-and-tourism freight (Miami, Jacksonville, Tampa, Port Everglades) and Central Florida last-mile distribution. The hurricane season — June through November — drives both stress and opportunity: insurance rates climb, freight rates spike around storm-recovery windows, and shutdown days are a real income variable. Florida has no state income tax. The traffic on I-95 and I-4 is consistently in the top tier of US congestion, so HOS planning around peak commute windows matters more here than in most states. Reefer and produce work pays well; OTR pulling out of the state is steady year-round.
Related guides
- Best trucking companies in Cutler Bay, Florida
- CDL driver salary in Cutler Bay, Florida
- Best owner-operator companies in Florida
Where this data comes from
Compensation, FMCSA safety, benefits, and operational performance — weighted 30, 25, 25, and 20 percent respectively. Compensation extends beyond headline pay to include sign-on bonus tier and settlement cadence. Benefits scoring differs by hiring type because the perks that matter to a W2 driver and a contractor are not the same. Updated September 2026.