Elon Musk has tweeted that the first orbital Starship upper stage prototype should be completed by June 2019. He has stated that the Super Heavy first stage will start construction in the spring.
Previously, Elon Musk has targeted the Super Heavy Starship to reach orbit by 2020. Elon has said the odds of making it to orbit by 2020 are at least 60% and rising rapidly.
If the Starhopper has successful testing from February through July, then an orbital test could happen in the latter half of 2019. SpaceX will be able to build the 38 Raptor engines for a full Super Heavy Starship.
If the new engines work and the new design enable this shortened development schedule then it seems SpaceX would try for orbit in late 2019.
SpaceX had the Falcon Heavy succeed on its first launch into space. The Falcon Heavy had 27 engines. The engines were similar in size to the Raptor engines.
SpaceX has landed many first stages.
The single piece Super Heavy seems like something that they will be able to take larger and larger test hops and then fly to orbit.
The Starship is seven engines and following the same development plan.
I think replicating the first launch success of the Falcon Heavy with both the Super Heavy and Starship is a possibility in 2019.
Elon Musk will be giving a new talk about the shiny stainless design for Spacex Super Heavy Starship after the first Starhopper flight.