The price includes a $750 destination charge.
The top-of-the-line Fortwo Cabrio with a dual-clutch automatic transmission is priced at $20,640, including shipping.
Smart last offered the convertible as a 2015 model with a price tag of $18,680, including shipping.
Designed to take on the Fiat 500C, the Fortwo Cabrio is equipped with a "tritop" folding soft top with removable roof bars.
Convertible tops are available in black and dark red.
The top operates at any speed and retracts in 12 seconds, while the roof bars store in the tailgate.
The Fortwo Cabrio is equipped with an 89-horsepower three-cylinder engine.
Edmunds says: Car shoppers in the market for an under-$20,000 drop top may want to check out the 2017 Smart Fortwo Cabrio.