The most charming town in all of North Wales is Conwy, a medieval walled village with an outstanding late-13th-century castle sited on a rocky headland overlooking the town, bay and river estuary of the same name. Climb up any of several towers for views of the town, the 1826-built Telford suspension and tubular railway bridges, the sea and the surrounding hills. The seafront is lined with fisherman's cottages, including the smallest house in Great Britain with a 9-foot-by-6-foot two-story floor plan. The main road enters the town via one of several stone gates that are connected by stone battlements and 22 towers. Much of the wall can still be walked.

The town has several historic buildings, such as the large Elizabethan-era residence of Pas Mawr and the National Trust's 15th-century Aberconwy House, both beautifully furnished. St. Mary's, a 13th-century Anglican church, is tucked in behind Castle and High streets. Both streets also house gift stores, food stores, restaurants, pubs and the attractive Castle Hotel, with multiple dining and drinking options. Conwy is an hour's drive or train ride from Holyhead.

Caernarfon Castle is probably the best known of North Wales' outstanding collection of fortifications, built during Edward I's reign. Completed in the late 13th century next to the Soient River, the king saw to it that his son, the first English Prince of Wales, would be born there. Hence, the castle was designed as a royal palace in addition to being a stronghold to protect English settlers. The most famous investiture took place there in 1969, when Prince Charles was crowned Prince of Wales. Climb the polygonal towers, and explore the many museum rooms dedicated to the history of the Royal Welch (archaic spelling) Fusiliers, Wales' proudest and oldest regiment. The castle dominates a large town square, where stalls selling souvenirs, antiques and fresh produce are set up. Just off the square is the terminal for the narrow-gauge, steam-powered Welsh Highland Railway that operates to Porthmadog and connects with the Ffestiniog steam railway. Caernarfon is an hour's drive or combined train and bus ride from Holyhead.

Beaumaris is the site for the largest and last of Edward I's line of medieval coastal fortresses built in Northwest Wales. The concentric design has a moat and both inner and outer walls, rendering it almost impregnable. It faces adjacent sheep pastures and the entrance to the Menai Strait, dividing the Isle of Anglesey from mainland Wales, and looks across the sea to the Great Orme headland at Llandudno. The adjacent town is also a charming stop for souvenir shopping, a meal and a walk along the sea front. Take a train to Bangor and connecting bus with a stop across the street from the station.

The narrow gauge Ffestiniog Railway, running over 13.5 miles of twisting mountain track, qualifies as the oldest continuously operated rail line in the world. Completed in 1832 to carry slate from Blaenau Ffestiniog to Portmadog, the line operates steam-powered trains for tourists and regular passengers. From Portmadog, the line first travels across a long causeway and enters pasture land before beginning a long climb, including a spiral track, past waterfalls and into the mountains of Snowdonia National Park. Treat yourself to first-class travel in the observation car positioned at the end of the train, which offers a big window looking back along the tracks. The line connects to standard gauge trains operated by Arriva Train Wales at both ends so you can make a continuous loop or go out and back via Portmadog, both options possible with the typical eight-hour port time allotted.

For a completely different outing and one usually not offered as a shore excursion, take the train from Holyhead to Llandudno, Wales' premier seaside resort, with its high Victorian character intact. (Trains run hourly, taking about 75 minutes, usually with a change at Llandudno Junction.) Nestled beneath the Great Orme, an egged-shaped limestone headland, Llandudno has all the ingredients that once drew and still draw lots of visitors to a splendid, crescent-shaped, seafront esplanade; arcaded shopping stores along Mostyn Street; a 1,234-foor pier with kiosks and amusements that extend out into the Irish Sea; and the Great Orme Tramway that, since 1902, has taken visitors to the top of the headland. On a clear day, the view extends out across the sea to the Isle of Mann and north to the Lake District. A scenic drive, leaving from the town center, circles the headland, and a vintage tour coach stops at viewpoints and close to the lighthouse that now operates as a bed and breakfast.

Visitors like to pause at Llanfairpwllgwyngyllgogerychwyrndrobwyll-llantisiliogogogoch, the longest place name in Europe, to have their photo taken in front of the sign at the local rail station. Located on the Menai Strait near the 1850-built Britannia Bridge, the name translates to "The Church of St. Mary in a white hollow by a hazel tree near a rapid whirlpool by the church of St. Tisilio by a red cave." The short form of the name is simply "Llanfair P.G." Besides a store (Pringles) selling woolen goods and souvenirs, there is not much else there. Shore excursions all pause there, and trains make a flag stop so you can snap your photo.