Updated November 2026
Best Trucking Companies in Kissimmee, Florida (November 2026)
Through November 2026, 252 carriers in Kissimmee, Florida employ W2 company drivers across the lanes Lanefinder tracks. Herrington Transportation Inc. leads with an average weekly pay of $2,000. 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 November 2026
Mountain States L.P. Gas at #4 and ARKA EXPRESS INC at #8 are new to the top 50 in Kissimmee, Florida. Biggest climbs: DICK LAVY TRUCKING (#30 → #6) and Herrington Transportation Inc. (#21 → #1). Biggest fall: REISCH TRUCKING INC (#28 → #46). Average weekly pay moved most at DICK LAVY TRUCKING (up 28.5% from $1,517 to $1,950). Elsewhere in the top 50, 2 carriers joined, 4 left, and 41 changed rank.
All changes since October 2026
| Carrier | Last month | This month | Change |
|---|---|---|---|
| Herrington Transportation Inc. | #21 | #1 | Up 20 places |
| True Transport Inc. | #5 | #2 | Up 3 places |
| JK MOVING & STORAGE INC | #1 | #3 | Down 2 places |
| Mountain States L.P. Gas | Not ranked | #4 | New |
| Covenant Transport Inc | #2 | #5 | Down 3 places |
| DICK LAVY TRUCKING | #30 | #6 | Up 24 placesweekly pay up 28.5% ($1,517 → $1,950) |
| PRAIRIE FIELD SERVICES LLC | #4 | #7 | Down 3 places |
| ARKA EXPRESS INC | Not ranked | #8 | New |
| South East Carriers INC | #3 | #9 | Down 6 places |
| G-DIAMOND TRANSPORT INC | #7 | #10 | Down 3 places |
| ELBERTA LOGISTICS INTERNATIONAL LLC | #8 | #11 | Down 3 places |
| Diaz Stone & Pallet Inc. | #6 | #12 | Down 6 places |
| MC CARRIER LLC | #10 | #13 | Down 3 places |
| BRADY TRUCKING INC | #9 | #14 | Down 5 places |
| A & H INC | #19 | #15 | Up 4 places |
| HOLLAND ENTERPRISES INC | #14 | #16 | Down 2 places |
| M&D TRANSPORT | #15 | #17 | Down 2 places |
| NEIER INC | #13 | #18 | Down 5 places |
| GALWAY BAY TRANSPORT INC | #20 | #19 | Up 1 place |
| G & C FOOD DISTRIBUTORS & BROKERS INC | #16 | #20 | Down 4 places |
| RIVER CITY TRANSPORT INC | #12 | #21 | Down 9 places |
| LUCKY WORLD INC | Not ranked | #22 | New |
| Excel Trucking LLC | #17 | #23 | Down 6 places |
| Creedence Energy Services LLC | #18 | #24 | Down 6 places |
| Z TRANSPORTATION INC | #23 | #26 | Down 3 places |
| AN ENTERPRISE INC | #22 | #27 | Down 5 places |
| Brenny Specialized Inc | #24 | #28 | Down 4 places |
| ROWLAND TRUCK LINES INC | #26 | #29 | Down 3 places |
| HUTCHINSON TRUCKING LLC | #27 | #30 | Down 3 places |
| COYOTE XPRESS LLC | Not ranked | #31 | New |
| Cross Integrated Transport, LLC | #34 | #32 | Up 2 places |
| REVV TRANSPORT | #32 | #33 | Down 1 place |
| Caravan Inc | #31 | #34 | Down 3 places |
| CTK LOGISTICS LLC | #33 | #35 | Down 2 places |
| Southland Transportation | #37 | #36 | Up 1 place |
| NTA, LTD. | #35 | #37 | Down 2 places |
| JL LOGISTICS INC | #36 | #38 | Down 2 places |
| VITAL TRANSPORTATION CORP | #40 | #39 | Up 1 place |
| Idea Transport LLC | #38 | #40 | Down 2 places |
| Bakers Express | #39 | #41 | Down 2 places |
| SEMO EXPRESS LLC | #41 | #43 | Down 2 places |
| S & R TRANSPORTATION LLC | #43 | #44 | Down 1 place |
| EAGLE EYE TRUCK LINES LLC | #44 | #45 | Down 1 place |
| REISCH TRUCKING INC | #28 | #46 | Down 18 places |
| LIBERTY HAULERS INC | #45 | #47 | Down 2 places |
| 1 MTX LLC | #46 | #48 | Down 2 places |
| Parks Motor Group Inc | #47 | #49 | Down 2 places |
| BROADWATER LOGISTICS & TRANSPORTATION INC | #49 | #50 | Down 1 place |
| WILLIAMS PRESTIGE ENTERPRISE | #11 | Not ranked | Dropped out |
| Frozen Food Express Inc. | #29 | Not ranked | Dropped out |
| Detmar Logistics | #48 | Not ranked | Dropped out |
| HORIZON TRANSPORTATION | #50 | Not ranked | Dropped out |
Kissimmee, Florida's top trucking carriers right now
The top of the list is Herrington Transportation Inc. at $2,000/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1Herrington Transportation Inc. — $2,000/wk
Herrington Transportation Inc. leads the Kissimmee, Florida market on combined pay and ranking score this month. Herrington Transportation Inc.'s weekly pay ranks in the 90th percentile across Kissimmee, Florida. The carrier tracks as a responsive employer on Lanefinder's data.
#2True Transport Inc. — $2,250/wk
True Transport Inc.'s weekly pay ranks in the 96th percentile across Kissimmee, Florida. True Transport Inc.'s FMCSA score is strongest on unsafe-driving avoidance — 98th percentile.
True Transport Inc. actually pays more weekly than the top-ranked carrier — $2,250/week.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC pays above the 89th percentile on weekly pay for the Kissimmee, Florida market. JK MOVING & STORAGE INC ranks in the 94th percentile for vehicle maintenance on FMCSA SAFER data.
Also in the top 10: #4 Mountain States L.P. Gas at $2,000/wk, #5 Covenant Transport Inc at $1,762/wk, #6 DICK LAVY TRUCKING at $1,950/wk, #7 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #8 ARKA EXPRESS INC at $1,750/wk, #9 South East Carriers INC at $1,600/wk, #10 G-DIAMOND TRANSPORT INC at $2,045/wk.
How drivers spend their time on the road in Kissimmee, Florida
17% of Kissimmee, Florida's active CDL postings are regional and 78% are OTR; local plus semi-local accounts for the rest (5%).
Across Kissimmee, Florida CDL postings: 2% with guaranteed pay, 29% dedicated, 81% take-truck-home, 62% pet-friendly, 66% riders-allowed.
How Kissimmee, Florida compares to Florida
Among the figures above, dedicated routes is where Kissimmee, Florida differs most from Florida — 10 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. Miami-area I-95 is among the more congested US corridors, 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 Kissimmee, Florida
- CDL driver salary in Kissimmee, Florida
- Best trucking companies in Florida
Where this data comes from
Compensation is the largest single weight at 30% — pay percentile, sign-on bonus, guaranteed-pay availability, and settlement cadence. FMCSA safety contributes 25%, built from five SAFER dimensions with unsafe-driving and hours-of-service weighted 2× heavier. Benefits contribute 25%, scored separately for W2 versus owner-operator and 1099 carriers. Operational performance — application responsiveness and fleet scale — contributes 20%. Updated November 2026.