Updated May 2026
Best Trucking Companies in Fort Myers, Florida (May 2026)
Lanefinder tracks 241 W2 trucking carriers hiring in Fort Myers, Florida. Rankings below reflect May 2026 data: pay percentiles, FMCSA safety, benefit prevalence, and operational performance. 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.
Where CDL pay is strongest in Fort Myers, Florida this month
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 tops the Fort Myers, Florida ranking with the strongest composite score across pay, safety, benefits, and operational signals. Weekly pay here lands in the 95th percentile across Fort Myers, Florida. Strongest FMCSA dimension is controlled-substances compliance — 88th percentile. Application-response data flags this carrier as a responsive employer.
#2True Transport Inc. — $2,250/wk
True Transport Inc. sits in the 97th percentile for weekly pay among Fort Myers, Florida carriers. True Transport Inc. ranks in the 99th percentile for unsafe-driving avoidance on FMCSA SAFER data. True Transport Inc. tracks as a responsive employer on application-response 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 sits in the 95th percentile for weekly pay among Fort Myers, Florida carriers. JK MOVING & STORAGE INC's top FMCSA dimension is unsafe-driving avoidance, in the 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 BRADY TRUCKING INC at $1,750/wk, #10 MC CARRIER LLC at $1,700/wk.
Lane mix and benefits across Fort Myers, Florida
Of active CDL postings in Fort Myers, Florida this month, 16% are regional and 83% are OTR (long-haul). Local and semi-local routes account for the remaining 1%.
Guaranteed pay is on offer at 2% of Fort Myers, Florida postings; dedicated routes at 27%; take-truck-home at 83%. Pet-friendly policies appear at 63% and riders-allowed at 66%.
Where Fort Myers, Florida differs from the Florida baseline
| Fort Myers, Florida | Florida top 50 | Delta | |
|---|---|---|---|
| Pet-friendly fleets | 67% | 76% | -9 pt |
| Dedicated routes | 37% | 29% | +8 pt |
| Riders-allowed policies | 73% | 80% | -7 pt |
Source: Lanefinder index, May 2026
The largest gap is on pet-friendly fleets: Fort Myers, 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 Fort Myers, Florida
- CDL driver salary in Fort Myers, Florida
- Best trucking companies in Florida
How we compile these rankings
Compensation (30%): pay percentile + sign-on bonus + guaranteed pay + settlement frequency. FMCSA safety (25%): weighted percentile across vehicle maintenance, unsafe driving, hours-of-service, driver fitness, and controlled substances. Benefits (25%): hiring-type-aware. Operational (20%): driver-application responsiveness, modulated by fleet scale. Updated May 2026.