From antiquity and the royal doctor Diphilo the Sifnian (personal physician to the king of Thrace, Lysimachus, who wrote the work "On the presentations of the diseased and the healthy”) or the Sifnian poet and pioneering musician and composer known as Filoxenidou or Theoxenidi, who introduced the musicological term "Sifniazein” '(to define certain complex melodies with a variety of tone and expressiveness), the tradition in sciences, literature and the arts continues to this day.
After the Middle Ages, Sifnos saw considerable cultural advancement, and a continued cultivation of literary pursuits. The first known school of the island was established in Kastro in the early 16th century. Since that time, elementary schools, Greek language schools, ‘Gymnasium’ higher-education schools, schools for girls, schools for scribes and orators, schools of iconography, and peer teaching schools, among others, make up the rich tradition of the island in the field of education. The crowning glory of all of these was the ‘School of the Holy Sepulchre’ (Panagia Tafou (from the mid-16th century). Also known as the ‘Paideftirion of the Archipelago’, it was the first educational establishment offering free higher education in Greece, and its reputation was well-known throughout the country. Students came from all over Greece to study at the school in Sifnos. Many graduates of the school became teachers, scholars, clergy, missionaries, church patriarchs, among other things. (More than fifty Sifnian graduates of the famous school went on to become church patriarchs and metropolitan bishops).
Among the teachers of the School of the Holy Sepulchre, also born and raised in Sifnos, was Nikolaos Chrysogelos, the Great Teacher of the Nation, the first Minister of Education of the Modern Greek state, legislator and founder of the Primary Education system and Peer Method Teaching in Greece (His bust stands in the main square of Artemonas, which is named after him).
And the tradition was continued by the ‘wave of Sifnian teachers’, who in the 19th and 20th century involved themselves in the cultural furtherment of Hellenism and were leading lights and educators in all aspects of the arts and letters: journalists, publishers and printers, folklorists, poets, lyricists, historians, painters, lawyers and legislators, artists ...
- Ioannis Gryparis, poet, renowned translator and educator from Artemonas, who served as first director of the National Theatre, and was honoured for Excellence in Arts and Letters by the Academy of Athens. (A statue of Ioannis Gryparis can be seen in the courtyard of the elementary school in Artemonas).
- Apostlos Makrakis, polymath philosopher, and a theologian much respected for his work. (His bust is in the square named after him in Katavati).
- Aristomenis Proveleggios from Exambela, poet, translator, Doctor of Philology, MP and academic. (His bust, a work by the renowned sculptor, Giannoulis Halepas, is in the courtyard of the Sifnos High Schools).
- Kleanthis Triantafyllos - Rampagas, militant journalist, publisher and satirical poet (his bust can be seen in the main square in Apollonia).
Other respected figures include
- the hagiographers Athanasios of Sifnos, (later Metropolitan of Thebes), Nikolaos Melissos, the monk Agapios Prokos, (who signed himself as "Defterevon of Sifnos"), Apostolos Sgourdaios, and others
- Karolos Gion, educator, historian, particularly of the islands, who wrote the ‘History of Sifnos Island’ in 1876
- Nicholas Dekavallas, Doctor of Philosophy of the University of Athens, and author of the ‘Historical Dictionary’ of the Academy of Athens
- Nikos G. Stafilopatis, publisher, writer, journalist, poet and editor of the ‘Anthology of Sifnian Poets’, who received an award from the Academy of Athens for his collection ‘Folk Songs and Christmas Carols in Sifnos’ (1998)
- Antonis Magganari-Dekavallas, lawyer, legislator, Doctor of Philosophy, university professor in the USA, and prize-winning poet recognised by the Academy of Athens.
- Stelios Sperantsas, doctor, poet and writer, President of the Union of Greek Writers and the Union of Medical Writers, who wrote textbooks for primary and secondary schools, receiving many awards and distinctions including the Silver Medal of the Academy of Athens for his contribution to children's literature. (The famous Christmas carol ‘Xionia sto Kambanario’ (Snow on the Bell Tower) is his!)
- Georgios Maridakis, Professor of Private International Law at the Law School of Athens University, and an academic.
- Theodosis Sperantsas, scholar, publisher, Mega Logothetis of the Church of Greece, writer, novelist and poet who was awarded the Gold Award of the Academy of Athens
- Manolis Korres, playwright, whose works have been translated and performed in many countries all over the world, President of the Greek Society of Playwrights, and director for over 20 years of the Theatrical Museum of Greece
- Antonis Prokos, author, award-winning poet, judge, President of the Court of Appeal and member of the Society of Greek Writers.
- Ioannis Maroulis, NikolaosMaroulis, and Konstantinos Panorios (many works by the latter are exhibited at the National Gallery).
- Konstantinos Dialisma, writer, poet, editor of the magazine "Anaplasis" and founder of the ‘Dialisma’ schools.
- Antonis Zilimona, judge, President of the Court of First Instance, and later President of the Supreme Court
- Maria Chrisogelos, first Greek woman lawyer at the Supreme Court.
- Iakovos Dragatsi, leading educator, archaeologist, and writer.
- Kostas Romanos, journalist, writer, poet and publisher Greek of English and Arabic newspapers in Cairo
- Emilio Dragatsi, scholar and playwright
- Nikolaos Kambanis, journalist and publisher
- Aristo Kambanis, poet, writer, translator, journalist, publisher and President of the Journalists Union of Athens Daily Newspapers .
- Aristides Prokos, lawyer, writer and poet.
- Aggelos Kosmi, author, lawyer and folklorist.
- the poets G. B. Prokos, Ioannis Vali, Ismene Karaiosifidou-Politou, Leandros Polenakis, Giorgos Likos (the first generation of postwar Greek Poets).
- Christos Koulouris, teacher, author and prize-winning poet.
- Lefteris Stavrianos, world-renowned historian, Professor of History at the Universities of North Western and California, author of much-discussed textbook ‘History of the Human Race’, whose books are still taught in the US.
- Manos Philippakis, ethnologist and scholar.
- Nikos Kalamaris, educator and author.
- the distinguished actresses Mary Arons, Eudoxia Stamatopoulou (Depasta), Eirini Vassilakis, Lela Patrikiou.
- Varvara Philippaki, archaeologist, who conducted the excavations of the Acropolis on Agios Andreas hill.
- Fragkiski Psacharopoulou- Karori, musician and producer of radio and television broadcasts for Hellenic Radio & Television, who envisioned and established music workshops on the islands, including the Sifnos Music Workshop (operating in Kato Petali, which is named after her.
- Stamatis Polenakis, well-known caricaturist and cartoonist active in the resistance movement during the German occupation.
- Nicholas Vernikos-Eugenides, shipowner and President of the Eugenides Foundation.
- Evangelos T. Pantazoglou, aircraft engineer, associate of Aristotle Onassis and acclaimed photographer of the island.
- Stylianos Prokos, inventor and benefactor, whose legacy is the Philanthropic Foundation named after him in the centre of the island.
- Antonis C. Troullos, teacher, ethnologist and writer who received the award from the Academy of Athens for his contribution to teaching and his body of work in 1988, and writers with the Gold Prize the European Writers Union in 2009.
- Filareto A. Vitali, writer, scholar, and preacher.
- Nikos A. Stavrianos, author, writer, researcher.
- Simos Miltiades Symeonidis, historian and author of the ‘History of Sifnos’ and ‘Sifnian Matters’ (Historical Almanacs of Sifnos - 22 volumes to date, published annually and financed by the Municipality of Sifnos).
- Titos Patrikios, lawyer, sociologist, author, translator and award-winning poet, recipient of awards from Italy, France and Germany, as well as the Grand National Prize in 1994. He also received the recognition of the Academy of Athens in 2008 for his body of work.
- Giorgos X. Matzouranis, journalist and writer, member of Journalists' Union of the Athens Daily Newspapers and the Hellenic Authors Society
- Nikolaos G. Prombona, educator (Headmaster of the Sifnos High School for 25 years), President of the Community of Apollonia (1974), and a writer, who offers his services to the local community from time to time, in honorary and unpaid positions.
- Mimis D. Lemonis, writer and poet.
- Ourania A. Kalogyrou, publisher and writer.
- Julietta Karori, poet and radio producer.
- Yorgos Brounias, poet, recipient of an award from the Academy of Athens in 2010 for his collection of poetry ‘Awning in the Wind’ (2009)
- Member of the European Parliament, Nikos P. Chrysogelos
- 10 Members of Parliament
- 2 Ministers
- countless popular poets, scientists and artists until the present day.
Today two local newspapers are in circulation on the island, ‘The Sifnian News’ and the ‘Sifnos’, which is the oldest newspaper in Greece (in continuous publication since 1880). There is also an on-line news site, ‘To Sifnaiko Fos’, "(‘The Sifnion Light’).".
The ‘Sifnian Research Society’ has organised on the island (1998, 2002, 2006, 2010) four International Symposia in Sifnos, with hundreds of speakers and delegates from around the world, and with interesting scientific papers and presentations relating to Sifnos (in antiquity, Byzantine times, Frankish occupation, and Ottoman rule, and in more recent times, also focusing on the architecture of the island, geology, ethnology and literature). The minutes of the Symposia conferences have been circulated in print and electronic format and are an important source of information on the history of our island.
In 2007, the Swiss National Tourism presented Sifnos with an award as the ‘Island of the Poets and Culture’.
Every year the island holds dozens of cultural events continuing its tradition in literature, the arts and culture in general.