Pittenweem is the home of the Fife fishing fleet and has a new fish market and refurbished granary containing the all-important ice-house. The harbour can be a bustling scene with fishing boats landing their catch early in the morning. The occasional brave seal will pop its head up in the harbour looking for scraps. At the start of the eastern breakwater, the Gyles, not open to the public, is a pleasant corner of sixteenth and seventeenth century houses restored by the National Trust for Scotland, a good example of the Dutch influence that this part of Fife is known for. Kellie Lodging, the distinctive honey-coloured tower in the High Street, has also been restored by the Trust, its ground floor occasionally open as an art gallery.

Found in Cove Wynd overlooking the harbour, St Fillan's Cave was a refuge for the seventeenth century Christian missionary, St Fillan. He lived in the cave and the site became a shrine to later pilgrims. This simple dwelling also gave the town its name. In the Pictish tongue, Pittenweem means place of the cave. The key to the cave is available from the 'Gingerbread Horse' gift shop and cafe in the High Street.

Three miles (5km) inland from Pittenweem, near the tiny village of Arncroach stands Kellie Castle. The Oliphant family owned this castle for two centuries before it was sold to the Earl of Mar and Kellie in 1613. It lay abandoned until taken over and restored by Professor James Lorimer, a distinguished legal expert. On holiday in Fife in 1877, he discovered Kellie Castle on a walk, windowless and deserted, practically a ruin. The professor and his family fell in love with it and acquired it from the Earl of Marr as improving tenants, which they certainly proved to be.