The "official" start point for the Scilly Walk is the tourist office on Pier Road, but for us, this makes for a much more interesting and quirky place to begin. Perryville House sticks out like an architectural sore thumb on Long Quay, with its candy-pink frontage, Moorish iron verandas, and elaborate, French-style plasterwork above the front door. Now a hotel, this place owes its dainty mishmash of styles to a (somewhat enthusiastic) 19th-century renovation of a much older building. Pause, admire, and move on.
Rounding a hairpin bend and entering Scilly, you'll pass the Spaniard Inn, one of the oldest pubs in the area. Built on the site of a ruined castle in 1650, it is named in honor of a local hero called Don Juan d'Aquila, the commander of a Spanish naval fleet who fought alongside the Irish at the Battle of Kinsale in 1601.
Effectively a miniscule suburb across the harbor from Kinsale, the village of Scilly—yes, pronounced “silly”—clings to a strong sense of its own identity. Its unusual name is thought to hark back to fishermen from the Scilly Isles (off the coast of Cornwall, England) who settled here during the 17th century.
To explore the area, follow the signposted pedestrian path that runs along the sea from Scilly to Charles Fort. (You can pick up maps of the full route at the Kinsale tourism office.) Take the right-hand road around the village, skirting along the coast, and join the marked pedestrian trail by the waterside. Along here are lovely views across the harbor to Kinsale and the stout remains of James Fort.
You’ll pass another tiny hamlet on the outskirts of Kinsale, Summer Cove, which is as sweet a place as its halcyon name suggests. Black-and-white toy-town houses, with splashes of green and red, face the harbor as gulls circle overhead and the waves froth and bubble along the harbor walls.
A short walk uphill from Summer Cove lies Charles Fort, built to defend the port from foreign invaders. Local lore has it that until the 19th century, access to this stretch of water was controlled by a massive chain floating on timber kegs between the two shores that could be drawn tight at a moment’s notice.
The Scilly Walk ends here, but if you continue to walk south along the sea, you’ll find another path that follows the headland to the tip of Frower Point, which affords great views across the harbor to the Old Head of Kinsale. The total distance from Kinsale to Frower Point is 8km (5 miles) each way, and every part of it is quite rewarding.