Polls show him well ahead of main opponents Stavros Malas, 45, a former health minister in Christofias' government who is backed by communist-rooted AKEL party, and independent Giorgos Lillikas, 52, a former foreign minister under the late President Tassos Papadopoulos.
If no one gets more than half of the votes, the top two candidates go to a runoff a week later, a scenario polls suggest is likely.
The victor will jump into the bailout fray immediately. Euro-area leaders are expected to decide on rescue package for Cyprus in the latter half of March and the country is fast running out of money to pay its bills. The new president will have to convince skeptical eurozone partners â¿¿ especially bailout-weary Germany â¿¿ that Cyprus is a credible partner that deserves help and isn't a tax haven where Russian oligarchs park their dodgy money.
"Cyprus has no option but to sign a bailout agreement," says University of Nicosia political science professor Hubert Faustmann. "Bankruptcy is not an alternative."
On the surface, a bailout appears straightforward. Cyprus, which represents a mere 0.15 percent to the eurozone economy, needs up to â¿¬17 billion ($22.84 billion) to shore up its economy and save its banks, crushed under the weight of their toxic Greek debt holdings. That's a fraction of the amount in the bailouts of Ireland, Portugal and Greece. But the sum is equivalent to the entire economy of Cyprus, raising concerns that it may not be able to repay the loans.
With Cyprus' fate in the hands of other euro area countries, campaigning has focused more on the candidates' leadership mettle rather than fleshing out complicated economic issues.
Anastasiades has close ties to European leaders on whose goodwill the country is counting, an image encapsulated in his ubiquitous slogan, "The Crisis Needs a Leader." The idea has gained traction among Cypriots, most of whom favor a bailout.