Walking around the two listed settlements of the island, Ano Symi (Chorio) and Gialos (the island’s port) feels like being inside a living painting with colorful mansions of wealthy merchants and captains of the past, built on the steep slope of the rock.
Gialos is full of bars, tavernas and cafes. Walking along its alleys you will come across the Clock Tower (1881), the sculpture of "Michalakis", which depicts a small fisherman with a fishing rod in his hand, the Maritime Museum of Symi and St. John’s Cathedral, with its pebbled courtyard and a stone bell tower.
Walk up the 500 stone steps of Kali Strata, connecting Gialos with Chorio (Ano Symi). This is the old commercial street of the island, along which you will find picturesque alleys, well-tended churches and well-preserved neoclassical buildings with pediments, skylights and tiled roofs, lavishly decorated pebbled courtyards and beautiful shops. The route will take you to the main square with its stylish cafes overlooking the Aegean Sea.
In Symi you’ll find the most important and greatest pilgrimage in the Aegean, the historic Monastery of Taxiarchis Michael Panormitis (6th century), where you will admire the Byzantine hagiographies and the baroque bell tower.
Visit the Archaeological - Folklore Museum, that hosts archaeological findings from the classical to the Byzantine era and folklore exhibits such as the representation of a traditional house of Symi and local costumes.
Take the path through the cypress forest to reach the area of Kourkounioti with the 11 restored Byzantine wine presses, which testify to the long history of viticulture on the island, that lasted to the end of the 18th century.
Walk up to the Castle of the Knights (14th century) at the highest point of Chora, offering panoramic views of the island. While you are in the Castle, observe the coats of arms of the Grand Masters in the fortifications and visit the church of Megali Panagia.
Visit Emporio, the second harbor of the island with the "twelve caves", one of the most enigmatic sights of the island. These twelve cave domes are said to have been used as catacombs, burial monuments, but also painting/sculpture workshops in the Byzantine era.
In Pontikokastro, admire the 20 windmills once used for grinding grain; some of them have been restored and are now used as residences.
The traditional settlement of Pedi is ideal for strolling along the vineyards, olive trees and citrus groves.