Breezy cliff-top walkways, fishing villages, and open beaches characterize Fife and Angus. They sandwich Scotland's fourth-largest city, the rejuvenated city of Dundee. Scotland's east coast has only light rainfall throughout the year; northeastern Fife, in particular, may claim the record for the most sunshine and the least rainfall in Scotland, which all adds to the enjoyment when you're touring the coast or the famous golf center of St. Andrews.

Fife proudly styles itself as a "kingdom," and its long history—which really began when the Romans went home in the 4th century and the Picts moved in—lends some substance to the boast. From medieval times its earls were first among Scotland's nobility and crowned her kings. For many, however, the most historic event in the region was the birth of golf, in the 15th century, which, legend has it, occurred in St. Andrews, an ancient university town with stone houses and seaside ruins. The Royal & Ancient Golf Club, the ruling body of the game worldwide, still has its headquarters here.

Not surprisingly, fishing and seafaring have also played a role in the history of the East Neuk coastal region. From the 16th through the 19th century a large population lived and worked in the small ports and harbors that form a chain around Fife's coast, which James V once called "a beggar's mantle fringed with gold." When the sun shines, this golden fringe—particularly at Tentsmuir, St. Andrews, and Elie—gleams like the beaches of Normandy. Indeed, the houses of the East Neuk villages have a similar character, with color-washed fronts, fishy weather vanes, outdoor stone stairways to upper floors, and crude carvings of anchors and lobsters on their lintels. All the houses are crowded on steep wynds (narrow streets), hugging pint-size harbors that in the golden era supported village fleets of 100 ships apiece.

North, across the Firth of Tay, lies the region of Angus, whose charm is its variety: in addition to its seacoast and pleasant Lowland market centers, there's also a hinterland of lonely rounded hills with long glens running into the typical Grampian Highland scenery beyond. One of Angus's interesting features, which it shares with the eastern Lowland edge of Perthshire, is its fruit-growing industry, which includes raspberries.

Known as the "City of Discovery" (after the RRS Discovery, a polar exploration vessel that set sail from this port in 1901), and as the United Kingdom's UNESCO City of Design, Dundee has a sophisticated arts and cultural scene and some beguiling sights. The ongoing regeneration of the city's waterfront has created a buzz, with the cliff-shaped V&A Dundee design museum making a bold statement beside the Tay. Today's Dundee makes a superb base for a cultural stay and from which to launch a number of day trips.