Kenmare occupies one of the finest positions of any town in Ireland — set at the head of the Kenmare River, the long sea inlet that separates the Iveragh and Beara peninsulas, with the mountains of Kerry rising steeply on three sides and the estuary opening to the south-west. It is a planned town, laid out in an X-shape by Sir William Petty in the 1670s as part of the Cromwellian plantation of Munster, and the clarity of that original plan is still visible in the two main streets that cross at the town square. The result is a town of unusual coherence and charm — compact, walkable, and possessed of a food and craft culture that is exceptional for a community of its size.

The Kenmare Stone Circle, a short walk from the town centre, is the largest stone circle in the south-west of Ireland and one of the finest in the country. Fifteen standing stones arranged in a circle about 15 metres in diameter, with a central boulder that may have served as an altar, it dates from the Bronze Age — somewhere between 3,000 and 4,000 years old. The setting is remarkable: the circle sits in a field with the mountains of Kerry visible in every direction and the estuary glinting below. It is free to visit, rarely crowded, and one of those ancient monuments that communicates something genuine about the depth of human habitation in this landscape.

Kenmare's food scene is one of the finest in Kerry and has been for decades. The town has a concentration of excellent restaurants that is disproportionate to its size — Mulcahy's, The Boathouse, and Packie's are among the most celebrated, but the standard is high across the town. The weekly farmers' market on Wednesdays in the town square brings together local producers of cheese, charcuterie, smoked fish, and artisan bread from across the peninsula. The seafood — particularly the Kenmare Bay mussels, oysters, and crab — is outstanding, and the proximity of the estuary means that much of what appears on menus was in the water that morning.

Kenmare is the ideal base for exploring two of the finest peninsulas in Ireland. The Ring of Kerry — the 179-kilometre circuit of the Iveragh Peninsula — begins and ends at Killarney, but Kenmare sits on the southern arc of the ring and is a far more pleasant base than the busier town to the north. The Beara Peninsula, which begins just across the estuary, is wilder, less visited, and in many ways more rewarding than the Ring of Kerry — the Healy Pass, the Beara Way walking route, the Dzogchen Beara Buddhist retreat centre on the cliffs above the sea, and the cable car to Dursey Island at the tip of the peninsula are all within easy reach.

The craft and independent retail scene in Kenmare is one of the best in Kerry. The town has a long tradition of lacemaking — Kenmare needlepoint lace, developed by the Poor Clare nuns in the 19th century as a means of supporting the local community during and after the Famine, is one of the finest lace traditions in Ireland, and examples can be seen in the Kenmare Heritage Centre. The independent shops along Henry Street and Main Street sell work by local craftspeople — jewellery, ceramics, knitwear, and artwork — at a standard that reflects the town's reputation as one of the most design-conscious communities in Munster. Kenmare's restaurant scene is equally strong; the town punches well above its weight for food, and an evening here is a good reason to stay the night rather than driving back to Killarney after a day on the Ring of Kerry.