Forget fashionable footwear, only your most comfortable shoes will cut it in Killarney. It's a walking town, and every trail is a history lesson. Journey on foot through Ireland's first national park, 26,000 acres of woodlands, sandstone mountains and low-lying lakes. When your feet wear out, take in Killarney National Park via boat from Ross Castle. And because there are more hotel beds in Killarney than in any other Irish town or city (besides Dublin), you'll always have a place to rest your head (and feet).

The “little nest” of Kenmare is part of the famed Ring of Kerry, making it a prime stop for a spot of lunch and a pint. But before you go on your merry way, check out the area’s Bronze Age stone circle, one of the largest in southwest Ireland. The peaceful glens and streams of Gleninchaquin make a wonderful backdrop for a picnic, which you can work off on a walk along the Kenmare section of the Beara Way.

Boasting a historical dockyard housing Henry VIII’s Mary Rose and Lord Nelson’s HMS Victory, Portsmouth has maritime heritage written all over it. Museums aside, the city still lives and breathes the sea—best exemplified in its nautical spirit, cobbled historic district, and sail-shaped Spinnaker Tower viewpoint.

Reborn as one of France’s most dynamic and culturally progressive cities, Nantes is a city that wears its innovation on its sleeve. Populated by artists, engineers, and students, its ever-changing skyline is anchored by medieval roots and a rich maritime heritage.

History lovers should know that Milan is not all about trendy shops and designer clothes. Among the city's many historical attractions are La Scala Opera, the Milan Cathedral, the National Museum of Science and Technology and Santa Maria della Grazie, the church that preserves da Vinci's "Last Supper".

Riccione is sun-soaked and stylish, an ancient Italian settlement with modern, global flair. Located in the heart of the Eastern Riviera, this coastal destination is the perfect place to sip a cocktail while lounging on golden sands. At night, party people spill from the open-air discos onto the beach, creating a surreal sort of everlasting outdoor party. Zip down a slide at a water park, spin it up on a guided cycling tour, or visit the nearby Misano World Circuit racetrack for an unforgettable getaway.

Sardinia’s largest city (with a little over 150,000 people) and its capital for centuries, Cagliari on the island’s south coast offers the perfect mix of recreation and exploration options. The five-mile-long Poetto Beach is among the best city beaches on the Mediterranean, and together with the adjacent Marina Piccola, satisfies all manner of sun and sea pursuits. Seekers of culture will love Cagliari’s old district, Castello, where 13th-century towers still guard the medieval city walls.

The largest city on the Adriatic Coast, seaside delight Split has been under Roman, Venetian, Austrian, French, Italian and Yugoslav control. There is an abundance of restaurants and wine cellars. Sites such as Diocletian's Palace and Mausoleum, the Grgur Ninski Statue and the Cathedral and Bell Tower of St Domnius justify its position as a UNESCO-designated World Heritage Site. The city's coves offer several lovely beaches, including central Bacvice. Ferries link Split to Dalmatian summer resorts.