Perhaps best known for Michel Legrand's haunting theme from the 1960s film musical Les Parapluies de Cherbourg (The Umbrellas of Cherbourg), Cherbourg-Octeville is no longer the thriving transatlantic port of a Belle Epoque heyday symbolized by the hyperelaborate façade of its 1882 theater, one of the few old monuments to survive World War II. Umbrellas are hardly the sunniest of city symbols, but the climate, though gusty, is generally mild, and the harbor town has enough character and attractions—especially the world-class Cité de la Mer—to warrant a day or two of sightseeing. Cherbourg absorbed Octeville in 2000 and they officially became one city.
It was back in 1686 that military engineer to Louis XIV, Sébasien Le Prestre de Vauban, first spotted Cherbourg's potential as a defensive port beneath the rocky 360-foot Montagne du Roule, but it took the completion of a massive breakwater in 1853 before Cherbourg could harbor ocean-going ships. The first transatlantic liner docked in 1869; these days, ferries ply the Channel to England (Portsmouth and Poole) and Ireland (Rosslare). You can take a short sea cruise around the bay from Port Chantereyne any afternoon from April through September (02–33–93–75–27).