Updated May 2026
Best Trucking Companies in Cutler Bay, Florida (May 2026)
As of May 2026, 239 carriers in Cutler Bay, Florida are posting active jobs for W2 company drivers. KEEP TRUCKING LLC leads with an average weekly pay of $2,200. True Transport Inc. follows at $2,250/week. 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 May 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Cutler Bay, Florida's top trucking carriers right now
The top of the list is KEEP TRUCKING LLC at $2,200/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1KEEP TRUCKING LLC — $2,200/wk
KEEP TRUCKING LLC is number-one in Cutler Bay, Florida this month on the composite ranking. The carrier ranks in the 95th percentile for weekly pay in Cutler Bay, Florida. KEEP TRUCKING LLC ranks in the 88th percentile for controlled-substances compliance on FMCSA SAFER data. The carrier tracks as a responsive employer on Lanefinder's data.
#2True Transport Inc. — $2,250/wk
True Transport Inc. sits in the 97th percentile for weekly pay among Cutler Bay, Florida carriers. Strongest FMCSA dimension is unsafe-driving avoidance — 99th percentile. The carrier tracks as a responsive employer on Lanefinder's data.
Despite ranking below #1, True Transport Inc. outpays the leader on weekly average — $2,250/week.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC pays above the 90th percentile on weekly pay for the Cutler Bay, Florida market. JK MOVING & STORAGE INC's FMCSA score is strongest on unsafe-driving avoidance — 94th percentile.
Also in the top 10: #4 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #5 Diaz Stone & Pallet Inc. at $1,750/wk, #6 DIVINE ENTERPRISES at $1,375/wk, #7 G-DIAMOND TRANSPORT INC at $2,045/wk, #8 ELBERTA LOGISTICS INTERNATIONAL LLC at $2,000/wk, #9 G & C FOOD DISTRIBUTORS & BROKERS INC at $1,650/wk, #10 BRADY TRUCKING INC at $1,750/wk.
How drivers spend their time on the road in Cutler Bay, Florida
16% of Cutler Bay, Florida's active CDL postings are regional and 81% are OTR; local plus semi-local accounts for the rest (3%).
Guaranteed pay is on offer at 2% of Cutler Bay, Florida postings; dedicated routes at 26%; take-truck-home at 80%. Pet-friendly policies appear at 61% and riders-allowed at 65%.
Cutler Bay, Florida vs Florida: the numbers that diverge
| Cutler Bay, Florida | Florida top 50 | Delta | |
|---|---|---|---|
| Pet-friendly fleets | 67% | 76% | -9 pt |
| Riders-allowed policies | 73% | 80% | -7 pt |
Source: Lanefinder index, May 2026
The largest gap is on pet-friendly fleets: Cutler Bay, Florida sits 9 points below the Florida baseline.
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 owner-operator companies in Cutler Bay, Florida
- CDL driver salary in Cutler Bay, Florida
- Best trucking companies in Florida
The methodology behind the rankings
Four weighted components. Compensation carries 30% and includes pay percentile, sign-on bonus tier, guaranteed-pay availability, and settlement frequency. FMCSA safety carries 25%, built from five SAFER dimensions. Benefits carry 25%, scored separately for W2 versus owner-operator carriers. Operational performance carries 20%, measuring application responsiveness and fleet scale. Updated May 2026.