Updated May 2026
Best Trucking Companies in Clearwater, Florida (May 2026)
Clearwater, Florida, May 2026: 253 active W2 trucking carriers. 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.
Clearwater, 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 tops the Clearwater, Florida ranking with the strongest composite score across pay, safety, benefits, and operational signals. The carrier ranks in the 95th percentile for weekly pay in Clearwater, Florida. Top FMCSA dimension here is controlled-substances compliance, in the 88th percentile. Application-response data flags this carrier as a responsive employer.
#2True Transport Inc. — $2,250/wk
True Transport Inc.'s weekly pay ranks in the 97th percentile across Clearwater, Florida. True Transport Inc. ranks in the 99th percentile for unsafe-driving avoidance on FMCSA SAFER data. The carrier tracks as a responsive employer on Lanefinder's data.
For pure pay maximization, True Transport Inc. beats the #1-ranked carrier weekly at $2,250.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC pays above the 90th percentile on weekly pay for the Clearwater, Florida market. On unsafe-driving avoidance, the carrier ranks in the 94th percentile per FMCSA SAFER data.
Also in the top 10: #4 Covenant Transport Inc at $1,762/wk, #5 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #6 KOTTKE TRUCKING INC at $2,000/wk, #7 Diaz Stone & Pallet Inc. at $1,750/wk, #8 DIVINE ENTERPRISES at $1,375/wk, #9 G-DIAMOND TRANSPORT INC at $2,045/wk, #10 ELBERTA LOGISTICS INTERNATIONAL LLC at $2,000/wk.
What Clearwater, Florida drivers actually run
Of active CDL postings in Clearwater, Florida this month, 17% are regional and 81% are OTR (long-haul). Local and semi-local routes account for the remaining 2%.
Guaranteed pay is on offer at 2% of Clearwater, Florida postings; dedicated routes at 26%; take-truck-home at 82%. Pet-friendly policies appear at 63% and riders-allowed at 66%.
Clearwater, Florida vs Florida: the numbers that diverge
| Clearwater, Florida | Florida top 50 | Delta | |
|---|---|---|---|
| Dedicated routes | 41% | 29% | +12 pt |
| Pet-friendly fleets | 71% | 76% | -5 pt |
Source: Lanefinder index, May 2026
Among the figures above, dedicated routes is where Clearwater, Florida differs most from Florida — 12 points above statewide.
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 Clearwater, Florida
- CDL driver salary in Clearwater, Florida
- Best trucking companies in Florida
Where this data comes from
Pay carriers in the same market against each other (30% of the score). Add a five-dimension FMCSA safety percentile from SAFER (25%). Score benefits based on whether the carrier hires W2 drivers or contractors (25%). Layer on employer responsiveness and fleet scale (20%). The weights are fixed and public. Updated May 2026.