Day 1: Edinburgh – Oban
Meet your guide at the prearranged departure point in central Edinburgh, and then hop inside an air-conditioned minivan and travel west through the beautiful scenery of Loch Lomond and Trossachs National Park.
Stop first in Kilmartin Glen, where Neolithic and Bronze Age remains abound. With more than 350 ancient monuments in the area, it is one of the most important archaeological sites in Europe. Walk in the footsteps of the first Scots at Dunadd Hill Fort and see the impressive standing stones of the Temple Wood Stone Circle.
Next, continue to the beautiful fishing town of Oban, known as ‘The Gateway to the Isles’ because of its link with the Hebrides. Then, after checking in to your hotel or guesthouse, enjoy the rest of the evening at your leisure.
Overnight: Hotel or guesthouse in Oban
Day 2: Oban – Glencoe – Isle of Skye (B)
Savor a delectable breakfast at your hotel or guesthouse, and then check out of your accommodation and travel to Glencoe — perhaps Scotland's most famous and most scenic glen.
On arrival, marvel at the breathtaking scenery and hear from your guide how the picturesque spot was the site of a terrible massacre in 1692 that took the lives of many members of the MacDonald clan.
After enjoying some free time to explore Glencoe independently, return to your minivan and continue on to Fort William, a settlement dominated by the UK's tallest mountain: Ben Nevis. Hop aboard the Jacobite steam train, considered one of the greatest train journeys (included May 16–August 29). When you reach Mallaig, enjoy a seafood lunch (own expense) before crossing the sea to the magical Isle of Skye.
Arrive in the delightful village of Kyleakin on Skye’s east coast and check in to your hotel or guesthouse, where you’ll stay for the next two nights. The rest of the evening is yours to spend at your leisure.
Overnight: Hotel or guesthouse in Kyleakin
Day 3: Isle of Skye (B)
Start the morning with a hearty breakfast at your accommodation, and then enjoy the rest of the day to explore the Isle of Skye as you wish.
Perhaps pull on your hiking boots and head to the Cuillin Mountains to lose yourself amid the spectacular scenery. Or, maybe visit Dun Beag Broch, a small fortress near the village of Struan that dates back to the Ice Age. You might even travel to Dunvegan Castle, the 13th-century home of the Macleod clan, or take a cruise to see the Loch Dunvegan seal colony.
Overnight: Hotel or guesthouse in Kyleakin
Day 4: Isle of Skye – Loch Ness (B)
After breakfast, check out of your hotel or guesthouse and journey to the harbor town of Portree. Make the most of some free time to explore the small island capital, and then head to Trotternish Ridge, which is formed by a series of landslips including the well-known craggy pinnacles of the Old Man of Storr and the dramatic sea cliff of Kilt Rock.
Next, cross back over the sea to the Scottish mainland to visit Eilean Donan Castle, which dates back to the 13th century. Used as a filming location in the 1986 movie Highlander, the ruins of the castle look out over three sea lochs, and the landmark is widely considered as one of Scotland’s most iconic sights.
Then, travel into the heart of the Highlands. Gaze out at the rambling green hills and other scenic sights of the Scottish countryside, and then arrive at your accommodation in Drumnadrochit, near the mysterious Loch Ness.
After checking in to your hotel or guesthouse, enjoy the evening at your leisure.
Overnight: Hotel or guesthouse in Drumnadrochit near Loch Ness
Day 5: Loch Ness – Edinburgh (B)
Following breakfast, gather your bags and check out of your accommodation. Then, with your guide and group, relax on the short journey to Loch Ness. Hop out of your minivan by the mysterious stretch of water to snap photos and look out for Nessie, the fabled Loch Ness Monster.
Should you wish, set off on a 30-minute cruise (own expense) from Clansman Harbour to Urquhart Castle. After taking in the sights from the water, disembark at the castle’s ruins and head inside (own expense) to explore at your leisure. (Note: Loch Ness cruise and admission to Urquhart Castle are included March 21–May 9; September 10–October 10.)
Alternatively, head to the Loch Ness Centre and Exhibition (own expense), which boasts seven themed areas crammed with more than 500 million years of history, mystery and legends of Loch Ness and its famous monster.
When the time comes, join back up with your guide and travel south to the battlefield of Culloden, the site of the short but brutal hand-to-hand Battle of Culloden in 1746 that marked the defeat of the Jacobite forces.
Next, visit a local distillery, where you can sample a wee dram of Scotch whisky (own expense). Then, catch glimpses of the stunning Cairngorm Mountains on route to Pitlochry. Enjoy free time in the charming town before traveling back to Edinburgh.
Your 5-day tour then concludes with a drop-off at the original start point.