Samaria at the time Jesus lived included cities and towns that were Greek and some that were Samaritan. The Samaritans were descended from the Assyrians who conquered before 700 B.C. who mingled with tribes of Israel. Samaritans were considered Gentiles by the Jews in Judea.
By PALÄSTINA und das OSTOJORDANLAND (Julius Hoffmann, Stuttgart, 1925), Public Domain, https://commons.wikimedia.org/w/index.php?curid=3717018
Galileans who traveled south to Jerusalem for the festivals often did not feel safe traveling through Samaria. They would head east across the Jordan River into Decapolis and then Perea and then walk or ride south on the east side of the Jordan. Often, they would then come through Bethany and come up to Jerusalem from there. You will see two places called Bethany on the map. Mary, Martha, and Lazarus lived in the Bethany that is next to Jerusalem.
Sychar or Sychor in the story of the Woman at the Well is also on this map in Samaria. You can see roads on this map that Jesus and His followers would have used.