In 2371, a holographic representation of a typical 19th century brig named USS Enterprise was recreated on the holodeck of USS Enterprise-D, as a setting for Worf's promotion ceremony to lieutenant commander. (Star Trek Generations)
|Pre-warp ships Enterprise|
|Sail: HMS Enterprize • Enterprise • USS Enterprise|
|Powered: USS Enterprise CV-6 • USS Enterprise CVN-65|
This Enterprise was portrayed in Generations by the Lady Washington. (Star Trek Encyclopedia 2nd ed., p. 140) She also played the role of the "HMS Interceptor" in the film Pirates of the Caribbean: Curse of the Black Pearl and was used as a model for the "RLS Legacy" in the movie Treasure Planet.
At 178-tons, the Lady Washington is much too small to be any of the HMS Enterprise sailing ships. Only two of the US Navy's Enterprise sailing ships are close in size; the third (commissioned 1799), and the fourth (commissioned 1832). Of those two, only the former was ever rigged as a brig (having been re-rigged as such in 1812), and it had a much more notable service record. Based on this evidence, the ship in Generations – if it was meant to be a specific ship – was probably the 1799 Enterprise. Regardless, there is no canon evidence to indicate that this vessel was intended by the writers to represent any particular ship in the established "real-life" Enterprise lineage.