Take an afternoon stroll with gelato in hand through the medieval maze of streets. Blessed with stunning nature and an easygoing pace of life, this immaculately preserved Adriatic fort may just be a perfect microcosm of Croatia.
The UNESCO World Heritage site may be tiny, but it has a big history. Its cobbled streets and 16th-century convents hark to its past as the trade center and capital of colonial Portuguese East Africa.
This handsome city may have lost some of its might as a medieval capital, but Lübeck’s immaculately preserved center, enveloped by the River Trave, stands as a timeless testament to its dazzling history.
The capital of the Maldives may share the same turquoise water as the country’s famed all-inclusive resorts, but that’s where the similarities end. The bustling hub of commerce and politics, Male has seen its population double to 105,000 in 20 years.
Key West, Florida
Relaxed and eccentric, this enclave is the epitome of an island city’s do-as-it-pleases independent spirit. Tin-roofed conch houses and fairy-tale mansions share the palm-fringed streets where Tennessee Williams once strolled and bars where Ernest Hemingway drank.
This tiny island of tile-roof houses, navigable only by boat during the summer rainy season, has been called Mexico’s Venice. Some consider the picturesque, man-made town one of the birthplaces of Mexican identity: It was from here the Aztecs are said to have launched for Tenochitlán, later to became Mexico City, in the 11th century.
This stunning Arctic Circle town is set against snowcapped fjords. In addition to spectacular northern lights views, it’s called the “Paris of the North” for its fashionable denizens, while the city center boasts an impressive number of charming old wood houses.
Floating in the cobalt Lake Constance, Lindau boasts centuries-old streets and beautifully aged gables that soar into the sky. The best way to enter is as seafaring merchants once did—through the harbor with its iconic Bavarian lion statue.
Santa Cruz del Islote, Colombia
This Caribbean outpost—not Manhattan—is believed to be the most densely populated island in the world. If urbanness is defined by proximity, Santa Cruz del Islote is its essence: Here, 1,200 people in single-family homes share just 2.5 acres (0.01 sq km).
With 42 beaches and verdant wilderness harmoniously merged with urban sophistication, surfers and business moguls feel equally at home in this southern Brazilian city, dubbed the Island of Magic.