As tens of thousands marched in the Russian capital, Mr Putin praised the "manly and cool lads" of the Night Wolves biker group.
Vladimir Putin has attended a biker show organised by a motorcycle club in Crimea, which Russia annexed from Ukraine five years ago.
The Russian president rode with the Night Wolves and posed for pictures and selfies in his leather jacket, while tens of thousands of Russians protested on the streets of Moscow.
Mr Putin shook hands with the biker club's leader Alexander Zaldostanov, and rode a Ural motorbike near the Crimean city of Sevastopol.
He said: "I am very happy that such manly and cool lads set an example for the young people in our country and show them how one should treat Russia. I congratulate you with your 10th anniversary and I wish you all the best. Thank you!"
His visit to the annexed peninsula came as sanctioned protests took place in Moscow, ahead of elections next month. Police rounded up scores of protesters at the rally and detained a leading opposition figure before it began.
It was quieter than the previous week's rally when more than 1,000 people were detained - some of them violently.
According to the White Counter monitoring group, 60,000 people attended the Moscow rally, and organisers claimed it was the biggest in Russia for eight years. Police said turnout was 20,000.A month of demonstrations over elections for the Moscow city legislature have turned into the biggest sustained protest movement in Russia since 2011-13, where people rallied on the streets against alleged electoral fraud. In Moscow, protesters shouted "Down with the Tsar!" and waved Russian flags, angry with the fact that opposition candidates have been refused permission to run in the city elections.
Mr Putin and the Kremlin have avoided commenting on the unrest.