Eight Ferraris, three Mercedes-Benzes, a Lamborghini and two other vehicles were involved in the pile-up in the southern prefecture of Yamaguchi.
No-one was seriously hurt, but the road was closed for six hours after the accident.
Media reports estimate the damaged cars are worth at least 300m yen ($3.85m; £2.46m) in total.
The drivers were on an outing to the city of Hiroshima
The sports cars – driven in convoy by a group of automobile enthusiasts – were on their way to Hiroshima, reports Japanese newspaper The Asahi Shimbun.
Police say they believe the accident, which took place on Sunday, happened when the driver of one of the Ferraris tried to change lanes and hit the crash barrier.
“A group of cars was doing 140-160km/h (85-100mph),” an unidentified eyewitness told Japanese broadcaster TBS.
“One of them spun and they all ended up in this great mess.”
Ten people received minor injuries in the crash, police said.
“I’ve never seen such a thing,” highway patrol lieutenant Eiichiro Kamitani told AFP news agency.