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The local parish church dates from the 16th century and nearby are the ruins of the priory. The priory was originally located on the Isle of May, 6 miles off the coast, however, a move to the mainland ensued when the administration was turned over to the Augustian monks of St Andrews. The move to Pittenweem eliminated the threat of invasions from sea pirates who were a menace to the original Isle of May site. The new priory brought a welcome boost to the area and as a flourishing town Pittenweem established itself as one of the most prosperous areas in Scotland.

The new priory had underground passages which led down to St Fillan’s cave. Prior to the existence of the harbour, the cave could only be reached by boat, which made it an ideal secret hiding place for local smugglers of the time.

Pittenweem is also steeped in witchcraft history and was once well known around the area for its harsh punishment of witches. Several witch trials took place in the town and the local witches were drowned in the loch at Kilconquhar

Crail
Crail East Neuk Burgh and became a Royal Burgh in the 12th century. Robert the Bruce granted permission to hold markets on a Sunday, in the Marketgait, where the Mercat Cross now stands in Crail. The decision caused such outrage in religious circles that John Knox delivered a sermon at Crail Parish Church in the Marketgait damning the fishermen of the East Neuk for working on a Sunday. Despite the protests, the markets were a huge success and were amongst the largest in Europe.

The Tolbooth in the centre of the town has a characteristic tower and a European style roof, similar to buildings in Holland. A fish makes up part of its quirky weathervane as a reference to an old local delicacy called ‘Crail Capon’, which was split, dried haddock.

The European influence literally rings true in the old town hall: the bell in the tower was brought over from Holland and is a permanent reminder of the town’s links with the Dutch.

Despite the fact that the ‘home’ of golf is now Crail’s neighbour, St Andrews, Crail was in fact the first to have a golf course. It may not, however, be a candidate for the world’s oldest course - one story holds that the Scots did not invent the game but that it was brought back by Scottish fishermen who discovered the Dutch playing a form of the game.

Anstruther is steeped in history and nearly every building in the village tells a story. A famous tale is of Buckie House, known as the ‘Shell House’. The house was embellished with shells by Alex Batchelor, who was obviously not content at only decorating his home as he extended his obsession to charging people to see his coffin, which funnily enough was also covered in shells. Even Robert Louis Stevenson, a visitor to the area as a young boy, made note in his Fife journals, of the pebble adorned house of the ‘agreeable eccentric’.