A short distance from Edinburgh is a landscape strewn with sturdy hill forts, ancient castles and ruined abbeys that hints at the tumult of the past. It's quite at odds with the picturesque rolling, if windswept, sheep-studded hills and quiet valleys that make all seem agreeably placid to today’s visitor. At its heart are the ruins of four medieval abbeys with Jedburgh, the most complete, the best to visit first for its insights into monastic life. Of the others, Melrose is both the pick of the bunch, and also close to Abbotsford, the sometime home of the Romantic novelist Sir Walter Scott, and a splendid receptacle for his engrossing collection of historical curios. There are fine country houses to visit, notably Mellerstain for its exquisite Robert Adam interiors, and Manderston, the enjoyable swan song of the Edwardian Country House. Anglers should note that the River Tweed is also one of Scotland’s finest salmon-fishing rivers.

Known as the Home of Golf, pretty St. Andrews appeals to even those with no interest in the game. Set on a wide bay, the town is dotted with medieval ruins, stately architecture, and—thanks to its large student population—plenty of cozy pubs.

Your biggest daily decision in Side may be whether to head east or west. The town’s West Beach is closer to hotels, has calm water and fine sand, offers watersports, and is (not surprisingly) popular. If you’re craving a more relaxed day, though, head in the opposite direction. The East Beach is a bit rockier, but it’s less crowded—you’ll find the locals here.