The Taiwanese government's Wang Yu-chi, who oversees the island's China policy, will meet his Chinese counterpart Zhang Zhijun for talks set to last until February 14.
The meeting in the eastern Chinese city of Nanjing is the fruit of years of efforts to normalise relations and will be the highest-level interaction since their split in 1949 at the end of a civil war.
That year, two million supporters of the nationalist leader Chiang Kai-shek fled to Taiwan -- officially known as Republic of China -- after losing the civil war to Mao Zedong's Communists.
Ever since, the island and the mainland have been governed separately, both claiming to be the true government of China, only re-establishing contact in the 1990s through quasi-official organisations.
While no official agenda has been released for the talks -- widely seen as a symbolic, confidence-building exercise -- Taiwan's Wang last month said they had "crucial implications for further institutionalisation of ties between the two sides".
Taiwan is likely to focus on reaping practical outcomes from the talks, such as securing economic benefits or security assurances, while China has one eye on long-term integration of the island, analysts say.
Beijing views Taiwan as a rebel region awaiting reunification with the mainland, and has repeatedly refused to renounce the possibility of using force to take back the island if necessary.
Detente and differences
The current political thaw of a decades-long stalemate comes after the two sides have made cautious steps towards economic reconciliation in recent years.
Taiwanese president Ma Ying-jeou of the Beijing-friendly Kuomintang party came to power in 2008, presiding over a marked softening in tone from Taipei towards its giant neighbour and reinstating direct flights between the two sides.
In June 2010, Taiwan and China signed the landmark Economic Cooperation Framework Agreement, a pact widely characterised as the boldest step yet towards reconciliation.
Yet despite the much-touted detente, Taipei and Beijing have still shunned all official contact, and negotiations since 2008 when Ma came to power have been carried out through proxies.
While these proxies -- the quasi-official Straits Exchange Foundation representing Taiwan and the Association for Relations Across the Taiwan Straits for China -- have achieved economic progress, they lack the power to broach deeper-held differences.
Analysts say that only government-level officials can settle the crux of a lingering sovereignty dispute that sees each side claiming to be the sole legitimate government of China.
The upcoming meeting will be watched closely to see whether it could pave the way for talks between Ma and his Chinese counterpart Xi Jinping -- although chances of that happening anytime soon are slim.
"The current interaction across the Taiwan Strait is quite positive," said Jia Qingguo, a professor of international studies at Peking University.
Ties have "been developing very fast, but the potential of this relationship has not been fully tapped (by) both sides," he said.
"But people should not expect too much out of it. It will take time for the two sides to get really integrated."
The mood surrounding the talks has already somewhat soured in Taiwan after Beijing refused to issue credentials to the Taipei-based Apple Daily and the US government-funded Radio Free Asia on the weekend.
Taiwan said Monday it would raise the issue of press freedom with China during the talks.