Just west of London, Reading offers redbrick Victorian buildings, medieval ruins, a thriving university, and pretty waterside walks along the Thames River. Its student community and annual rock-music blowout—the Reading Festival—add an offbeat edge.

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.

Gazing over the English Channel, Hastings mixes black-tarred fishing huts with pebbly shores, Victorian architecture, and artsy shops that together draw boho travellers and families in search of seaside holidays. With a maritime museum, castle ruins, and a notable battle site, it’s also rich in history.

If you saw Chevy Chasy's masterpiece European Holiday, you'll recognise Stonehenge's massive formation. (As a citizen of the world, you should recognise Stonehenge anyway.) The prehistoric stone circle is eight miles from Salisbury, and its visitors provide a boost to the local economy. With a history dating back over 5,000 years, there is no shortage of significant places to visit in and around Salisbury. On the "must see" list are Salisbury Cathedral, Longleat and Stourhead gardens (and Stonehenge, of course).

A rare year-round resort on the Island of Winds, Alghero makes an atmospheric destination. Occupying armies have all left their marks on the old, walled city; Italian kingdoms, Carthaginians, Phoenicians, Byzantines, Arabs and Catalans have all come and gone. Offering an irresistible combination of history, architecture, culture, stylish shopping, fine food and wine, and water sports, Alghero's cobblestone streets can be explored on foot or by bus. Don't miss spectacular sea cave, Neptune's Grotto.

Oia is carved out of the cliffs, and visitors can see houses built for Venetian sea captains as well as the more typical "cave houses" of the villagers. You’ll find the pure white buildings with colourful roofs that are typical of Greek architecture, and you’ll probably enjoy poking around the town. But don’t breeze through in an hour—you must stay for the sunset. It’s legendary. Watch from a café, or, better yet, from a boat—you’ll be spellbound.