A Puglia port town that’s equal parts historic and functional, Monopoli makes a splash with medieval churches and castles jutting above the Adriatic. It’s also a painter’s dream, with bright blue fishing boats adding a pop of colour against whitewashed harbour walls.

Best known as the site of Napoleon’s exile, Elba’s long history stretches back to pre-Roman times, when it was settled by Ligures and then Etruscans. It’s Tuscany’s biggest island and Italy’s third-largest, offering a great mix of options both cultural (like hilltop towns and castles) and recreational (like hiking, biking, swimming, diving and beaching). There’s an airport at Marina di Campo, but most arrive by ferry from Piombino to Portoferraio (the biggest town), Rio Marina or Porto Azzurro.

The largest of the twelve Dodecanese islands on the Aegean's eastern edge, Rhodes is also its most popular. The well-preserved medieval city of Rhodes sits at the north of the island of the same name. High rise hotels line the northern and eastern coastlines. Small villages and resorts dot the island's other shores. Whether your interests are beaches, bars or ancient sites, Rhodes offers an abundance of all three. Authentic Greece can be found in the hilly interior of the 50-mile long island.

Southwest of London is Southampton (Soton to the locals), a metropolitan area centered around the port. However, tucked away on the side streets are ancient gems such as the Tudor House, Mottisfont Abbey, and "God's House," a museum located in a tower in the medieval wall. The ultra-modern Sea City Museum celebrates Southampton's seafaring past and the RMS Titanic. Looking for nightlife? Travelers can dance the hours away with bars, clubs, and live music, all accessible by public transportation.