Which place is the ancient Nanjing dialect more similar to?

Well, Nanjing’s geographical location is quite special, but generally speaking, it still belongs to Jianghuai Mandarin. It is the dialect of the cities in the Jianghuai area. The dialect spoken in Quanjiao County, Chuzhou, Anhui is almost indistinguishable from Nanjing dialect.

As for the Yangzhou dialect spoken by the original poster and the Suzhou dialect, well, they are very different. Suzhou, Wuxi, Changzhou, Shanghai, Jiaxing, and Hangzhou are all Wu-speaking areas, which is "Wunong Ruanyu". However, Shanghainese dialect is special because many people from northern Jiangsu have immigrated to Shanghai. Many small words in Shanghainese dialect are from northern Jiangsu, such as "jiegun" (awesome), "budaga" (describing the two have nothing to do with each other), "zan" "(Third tone, good description), Shanghainese dialect is a mixture of Suzhou dialect, Ningbo dialect, and Northern Jiangsu dialect, with Suzhou dialect being the dominant one.

Nanjing also belongs to the Jianghuai dialect area, which is somewhat similar to Zhenjiang dialect and Yangzhou dialect, but it has a great feature, that is, many Anhui people and northerners live in Nanjing, so Nanjing dialect is seriously northernized. Many things that should not be present in southern dialects, such as retroflex sounds, are present. Therefore, many people think that Nanjing dialect is weird and unpleasant.

To sum up, in ancient times, Nanjing dialect was still partial to the Jianghuai area, which was a mixture of Yangzhou and Huaian dialect.