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The largest concentrations of sights in Skopje are found in Centar and the Stara Čaršija (Old Town). The former is the modern hub of the city and contains newer attractions, while the latter is home to many of the city's historical sights. Outer Skopje is home to larger sights that are more spread out.

The Skopje Fortress stands above the Stara Čaršija, the city's historic bazaar, on the right bank of the Vardar. Countless Ottoman-era structures makeup the Stara Čaršija. Minarets from mosques like the 15th century Mustafa Pasha Mosque dominate the district's skyline. The oldest of these mosques dates from 1436. Of the remaining Turkish baths, two are in good condition and now serve as museums. The three caravansaries in the Old Bazaar feature lovely courtyards and are open to the public as cafes or museums. While Islamic buildings are prevalent in the Stara Čaršija, it is also home to central Skopje's most important church, St Saviour Church, known for its wood-carved iconostasis.

One of the main symbols of Skopje, the Stone Bridge connects the Old Town to Centar on the left bank of the Vardar. Centar is home to the main government offices of the Republic of Macedonia. It is also home to Macedonia Square, the city's central square. The face of the square has changed in recent years with new buildings constructed in older architectural styles, as well as the addition of massive monuments like that of Alexander the Great, the centerpiece. Another major piece of the recent changes to Centar is Porta Macedonia, a large triumphal arch. The city's best museums are found in Centar, such as the Museum of the Macedonian Struggle, the Holocaust Museum, and the Mother Teresa Memorial House.

Some of Skopje's best sights are found outside the city centre. Matka Canyon is one of Macedonia's gems, both culturally and naturally. It is home to numerous medieval churches and monasteries, often hidden in the scenic mountains. Mount Vodno is capped by the Millennium Cross, overlooking the city. In addition, archaeological sites dot the area, like the 55-arch Skopje Aqueduct. The Skopje Zoo contains a few hundred animals.