Edinburgh to Inverness (196 miles)
In Edinburgh, rent a Mini Cooper S—a sporty classic that hugs the winding Scottish roads nicely—at Eastern Mini (rentals from $112 per day). Leaving town, take the A92 to the A915 and head for St. Andrews, the birthplace of golf. Check out the first hole at the Old Course, where a public path crosses the famous fairway, then pop into the Peat Inn (lunch for two $51), just outside town, for roasted breast of pheasant and Ayrshire bacon. Back on the road, you’ll pass through green fields along the A913 before merging with the M90 and the A9, which leads to Inverness, the Highlands’ unofficial capital. Check in to Glenmoriston Townhouse (doubles from $208), a 30-room inn with views of the Ness River. For dinner, it’s the Mustard Seed (dinner for two $80), a 25-table restaurant set in a former church, serving up dishes like pan-seared fillet of salmon with soy-infused noodles.
Inverness to Broadford (99 miles)
Start by mid morning and drive southwest along Loch Ness via the A82. While glimpses of Nessie are highly unlikely, the ruins of Urquhart Castle are worth a look. Fort Augustus follows, where a lunch of fish-and-chips at Canalside Chip Shop (lunch for two $19) is a must. Beyond town, the drive gets a bit more rugged. Make a right onto the A87 and ascend the banks of the Garry River before leveling out at Loch Cluanie, whose surrounding peaks have an almost Alpine feel. From here it’s a quick descent through Glen Shiel—a glacier-carved valley—back down to sea level, over the Skye Bridge and into Broadford, on the Isle of Skye. Stay at the slate-roofed, 11-room Broadford Hotel (doubles from $205), and reward yourself with Highland venison sausages at the Spinnaker Lounge (dinner for two $60), the hotel’s rustic restaurant.
Broadford to Portree (70 miles)
Heading northwest the next morning, continue on the A87 to Portree, with its tiny harbor and pastel-colored cottages. For lunch, stop at Harbour View Seafood Restaurant (lunch for two $50) for briny Loch Harport oysters on the half shell. Behind the wheel again, hop on the A855, which follows the coast of the Trotternish peninsula, and keep your eyes peeled for the Old Man of Storr, a fingerlike rock formation on your left side. Just past the village of Staffin, turn left onto a road marked Quiraing, a 10-mile mountain route that winds through some of Scotland’s most scenic and untamed terrain. On the other side, follow signs for the A87; from here it’s a 16-mile drive back to Portree, home to Skye’s first boutique property, the Bosville Hotel (doubles from $205).