Transportation of horses to slaughterhouses can pose a welfare concern, in particular when horses are unbroken/unhandled. This study aimed to describe their journeys and journey conditions, document their welfare status on arrival in a slaughterhouse in Italy, and investigate possible associations between journey conditions and welfare issues. A total of 395 unbroken draft horses in 20 different consignments were assessed with a standardized protocol. The most common departure point (16/20 consignments, 80%) was a French assembly center, but many of these horses had Spanish passports, suggesting they had previously been transported from Spain to France. The average journey duration was 34 ± 14 h, including journey breaks (i.e., short stops inside the vehicle and long resting stops at control posts), while transit time was 24 ± 4 h. The drivers were well experienced, the trucks were well equipped (i.e., forced ventilation, drinkers), and the horses traveled loose in small groups (n ≤ 4 horses) within pens inside the vehicle. On arrival at the slaughterhouse, the horses self-unloaded and showed minimal behavioral and health problems. The prevalence of injuries, diarrhea/abnormal feces, and nasal discharge were 1.52%, 6.58%, and 4.30%, respectively. Cold temperatures, space allowance, and lack of feeding during transport were found to be the main hazards of those problems (all p < 0.05). Our findings confirm that the correct assessment of the fitness for transport, adequate journey conditions, and experienced staff are crucial factors to safeguard the welfare of unbroken horses during long journeys.