You can click on the medals to see the reverse.
The obverse bears bust of Dante Alighieri facing right. Around top, AMERICAN SONS OF ITALY; around bottom, "VINCA · TUA · GUARDIA · I · MOVIMENTI · UMANI!"; to left and right of bust, 1265 - 1321
The reverse bears laurel and oak branches around central field. Around top, SONS OF ITALY GRAND LODGE; around bottom, STATE OF - NEW YORK; in central field, FOR EXCELLENCE IN ITALIAN / TO / ANGELINA GUARDINA
The Order of the Sons of Italy is the largest and oldest national organization for men and women of Italian heritage in the United States. It was founded on June 22, 1905 by Dr. Vincenzo Sellaro to help assimilate Italians into American society during the immigration boom of the early 20th century. In 1928 Dr. Sellaro was given the key to the City of New York in recognition of his social and medical achievements.
1921 was the 600th anniversary of Dante Alighieri's death and the medal celebrates both the poet and the Italian language. It was awarded to young students for excellence in Italian. The Italian quote on the obverse is from the 33rd Canto of Dante's Divine Comedy and translates to:
"May your protection curb his mortal passions!"
The medal measures 68.9mm in diameter and was struck by the Medallic Art Company of New York.
References: MACo 1921-080