Pack a lifetime of outdoor adventure into just 14 days when you hike the highlights of Scotland. It starts with three days on the country's most scenic trekking route—the West Highland Way—which passes through gorgeous Highland scenery. That's just the beginning, as you'll then travel on a historic steam train to two of the most beautiful isles in the country: Skye and Islay. Here you'll hike around otherworldly mountains, explore rugged coasts, and reward yourself with some of the best whiskey in the world.


  • Trek for days along the famous West Highland Way
  • Experience the wild beauty of Rannoch Moor & Glen Coe
  • Hike up Ben Nevis, the UK's highest peak
  • Explore the coastal scenery and quaint villages of Skye
  • Enjoy great beaches and whiskey on Islay

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive at Bridge of Orchy Bridge of Orchy
Day 2 West Highland Way: Day 1 Glencoe
Day 3 West Highland Way: Day 2 Kinlochleven
Day 4 West Highland Way: Day 3 Fort William
Day 5 Fort William & Ben Nevis Fort William
Day 6 Transfer to the Isle of Skye & Jacobite Steam Train Broadford
Day 7 Explore the Isle of Skye: Day 1 Broadford
Day 8 Explore the Isle of Skye: Day 2 Broadford
Day 9 Isle of Skye to Glasgow Glasgow
Day 10 Glasgow City Tour Glasgow
Day 11 Isle of Islay: Day 1 Islay
Day 12 Isle of Islay: Day 2 Islay
Day 13 Isle of Islay: Day 3 Islay
Day 14 Islay to Glasgow & Departure  

Detailed Itinerary

Day 1: Arrive at Bridge of Orchy

The winding paths of the West Highland Way.
The winding paths of the West Highland Way.

Welcome to Scotland! This country in the northern British Isles is famous for its historic medieval cities, unspoiled Highlands region, and untamed islands off the west coast. You'll experience all of it on a hiking adventure over two weeks that will test your endurance and reward you with some of the most incredible scenery.

There's no time to waste, as right when you arrive in the city, a personal driver will be waiting to whisk you off to the Highlands. Your adventure begins right in the heart of this mountainous region, specifically Bridge of Orchy. This village is situated at the start of the West Highland Way, Scotland's most famous long-distance hiking trail. The route begins inland north of Glasgow and runs 95 miles (154 km) southwest towards the coast.  

Upon arrival at Bridge of Orchy, you'll settle into a local inn. Make sure to get a good night's rest, as tomorrow you're off to hike the West Highland Way.

Day 2: West Highland Way: Day 1

Glen Coe's dramatic volcanic landscape.
Glen Coe's dramatic volcanic landscape

Your first day's trek on the West Highland Way takes you 13 miles (21 km) through the beautiful and remote Rannoch Moor before crossing Glen Coe, a volcanic valley home to some of the most spectacular mountain scenery in the UK. Pass the impressive Buachaille Etive Mor to arrive at Kingshouse, one of Scotland's oldest inns and your base for the night.

Day 3: West Highland Way: Day 2

The shores of Loch Leven.
The shores of Loch Leven

Day two starts with a hike from Kingshouse over the Devil's Staircase, the highest point on the West Highland Way. A steep ascent climbs 1,797 feet (548 m), rewarding you with sweeping views over Glen Coe and Ben Nevis. After 10 miles (16 km) of trekking, you'll finish up the day on the pristine shores of Loch Leven, where you'll settle in for the night in the secluded village of Kinlochleven.

Day 4: West Highland Way: Day 3

The trail to Ben Nevis, just outside Fort William.
The trail to Ben Nevis, just outside Fort William

On today's 14-mile (23-km) section of the West Highland Way, you'll pass Lairig Mor, cross the beautiful valley of Glen Nevis, and skirt the foot of Ben Nevis. The adventure comes to an end at the loch-side town of Fort William, where you will spend the night. Known as the "adventure capital of the UK," this idyllic town's location between crystal clear lakes and snow-capped mountains draws outdoor enthusiasts from around the world.

Day 5: Fort William & Ben Nevis

Hikers on the ascent to Ben Nevis.
Hikers on the ascent to Ben Nevis

This will be your last chance to enjoy the Highlands before heading off to the Isle of Skye tomorrow. Because more hiking adventures await on the Scottish isles, you can take today to relax and recharge. Maybe visit a local distillery and fortify yourself with some quality Scotch whisky. Or, if you can't stay still, you can lace up your boots and hike nearby Ben Nevis. At 4,413 feet (1,345 meters), this is the UK's highest mountain.

It's a relatively easy ascent, as the trail starts from around sea level and takes about four hours to reach the summit. Once there, you'll be treated to jaw-dropping views across the Highlands and lochs. This is an unguided hike, but you can arrange for a local mountain guide to lead you. Along the way, they will share the rich history of Ben Nevis plus details of its landscapes, including how the surrounding flora changes with the increase in altitude.

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Day 6: Transfer to the Isle of Skye & Jacobite Steam Train

The Jacobite Express crosses the Glenfinnan Viaduct on its way to the coast.
The Jacobite Express crosses the Glenfinnan Viaduct on its way to the coast

In the morning, you'll board what's been described as "the greatest railway journey in the world." The Jacobite is a steam tourist train that passes through some of the most beautiful parts of the West Highlands. The one-way route is 42 miles (67 km) between the villages of Fort William and the charming fishing village of Mallaig.
On this trip, you'll witness an impressive array of extremes. It begins near Ben Nevis (the highest mountain in Britain), passes the deepest freshwater loch in Britain (Loch Morar), and travels alongside the shortest river in Britain (River Morarbefore). Other unforgettable wonders you'll see on this route include Loch Eil, the Glenfinnan Viaduct, and the silver sand beaches around the town of Arisaig
Glenfinnan is a historic landmark in that it's a railway viaduct built at the turn of the 20th century. It runs 1,000 feet (304 m) amid stunning Highland scenery that includes towering peaks, colorful moorlands, and the glassy waters of Loch Shiel. It's no surprise that the viaduct was featured prominently in the "Harry Potter" films—even the Jacobite locomotive had a starring turn as the Hogwarts Express.

The end of the line is the village of Mallaig, which also boasts stunning white-sand beaches. Here you'll catch a ferry to the Isle of Skye, the largest island of Scotland's Inner Hebrides archipelago. Upon arrival on the southern coast, you'll transfer to Broadford. Serving as your base for the next three nights, this pretty fishing village sits beneath the matronly eminence of Ben na Calliach (Hill of the Old Woman). 

Over the next few days, you won't lack for adventures and outdoor excursions. Skye is well known for its rugged coastline of gorgeous coves and peninsulas radiating out from a mountainous center—and you'll get to explore much of it. As well as daily walks and hikes, you'll have plenty of options for excursions like boat tours, bicycle rides, kayak lessons, and seaplane trips.

Day 7: Explore the Isle of Skye: Day 1

Elgol Beach on Skye's south west coast.
Elgol Beach on Skye's southwest coast

Today you'll have your pick of several short hikes and unique places to visit on Skye. One option is to ride a local bus to the stone ruins of villages like Boreraig and Suisnish. There are great coastal views to admire along the way.

Or perhaps head further south and take a ferry from the village of Elgol to Loch Coruisk. The trip passes romantic islets on the way to the loch, nestled amid the Cuillin Hills' sharp ridges. Along the way, you'll spot wild seabirds like oystercatchers, puffins, and herons. You'll also see plenty of seals and maybe even a basking shark or two.

For more untamed landscapes, cross over from the south of Skye to the Isle of Rùm and enjoy a few hours of hiking. Whatever you decide, you'll have all the information you need to get the most out of this incredible region. Retire to your small guest house in Broadford at the end of the day.  

Day 8: Explore the Isle of Skye: Day 2

Old Man of Storr, one of Skye's highlights

For your second day on Skye, you'll take a private tour of the island's most famous site. The first stop is the geological wonder of Trotternish, the northernmost peninsula of the isle. Here you'll see Old Man of Storr (featured in the movie "Prometheus"), an otherworldly rock pinnacle overlooking the Sound of Raasay.

Continue a short way north up the coast to Kilt Rock, massive basalt columns that tower 295 feet (90 m) over the coast and resemble a Scottish kilt. There's also Mealt Falls, which plunge 200 feet (60 m) over the cliffs to the rocky coast below. Next, visit the strange landscape of Quiraing, the northernmost summit on Trotternish. 

Continue west across the island to Dunvegan, the only remaining inhabited castle on the island. Home to Clan MacLeod for the last 800 years, the castle was rebuilt in the 19th century. A tour of the property and its five acres of colorful gardens is an unforgettable way to learn the history of the longest continuously occupied castle in the country. At the end of the tour, you'll return to your guesthouse and will have the evening free.

Day 9: Isle of Skye to Glasgow

Welcome to Glasgow's George Square

In the morning, you'll bid a farewell to magical Skye and the Scottish Highlands as you transfer a few hours south to Glasgow. This port city on the River Clyde is a fascinating place. It rivals Scotland's capital of Edinburgh, as it's more populous, plus it boasts a world-class art scene and historic architecture ranging from Victorian to Art Nouveau. Upon arrival, you'll check in to your hotel and will have the remainder of the day to explore Glasgow on your own.

Day 10: Glasgow City Tour

Glasgow's Kelvingrove Art Gallery

Today you'll head out into the city and visit some of Glasgow's famous landmarks. One highlight is the Glasgow Cathedral, built in 1197 and is an impressive example of Gothic architecture. Not only is it the oldest building in Glasgow, but it's also the oldest cathedral in mainland Scotland. 

Another stop is the incredible Kelvingrove Art Gallery and Museum, which opened in 1901 and is one of Glasgow's most popular tourist attractions. It's a striking piece of architecture done in the Spanish baroque style and fashioned out of red sandstone. Inside, you can explore 22 galleries featuring unique exhibits that run from art and architecture to animals and ancient Egypt. After seeing the sights, you'll return to your hotel and will have the evening free.

Day 11: Isle of Islay: Day 1

The dramatic coastline of Islay

in the morning, you'll head to the airport and catch a 45-minute flight west from Glasgow to the Isle of Islay. This is the southernmost of the Hebrides islands, known for its stunning beaches and world-class whiskies. Upon arrival, you'll check into your guesthouse, unpack, and can then plan your itinerary. 

Over three days, you can choose to do as much or as little as you like. You should see as much of the island as you can, and local bus services are a quick and convenient way to get you around the island. Or, if you're up for a bit of exercise, there are plenty of trails to explore that will put you in close contact with the island's diverse array of wildlife. Besides deer, gray hares, European otters, and seals, Islay is home to over 200 species of birds, including terns, cormorants, and oystercatchers.

Day 12: Isle of Islay: Day 2

Perhaps visit one of Islay's many distilleries 

The Isle of Islay is probably best known for producing its signature peaty, smoky whiskies. There are nine whiskey distilleries on the island, with more to come in the future. The first was founded in 1779, and ever since, the whiskies that come from this region are consistently ranked as some of the best in the world. 

Today you'll have free time to explore the island however you like, but you'd be remiss if you didn't head to one of the local distilleries for a tour and tasting. These are spread throughout the island, so there should be an option close at hand. Know also that there's a concentration of three great distilleries on the island's south coast—Ardbeg, Lagavulin, and Laphroaig—collectively known as the Kildalton Distilleries

Each of these distilleries is open to the public for tours, and each of their whiskies is unique. Ardberg is known for its heavily peated style; Lagavulin has a rich and heavy "seaside smokiness;" and Laphroaig is the best-selling whiskey on the island, famous for its medicinal, peaty tang. You'll have to stop by each one and decide which is the best.

Day 13: Isle of Islay: Day 3

Singing Sands Beach, on Islay

Spend your final day on this island however you like. Know that Islay has 130 miles (209 km) of coastline featuring stunning bays, coves, sea cliffs, and beaches. If the weather is favorable, head to one of the island's unspoiled stretches of sand like Machir Bay, Singing Sands, or the Big Strand—the last of which is famous for its dramatic sunsets. 

Another option is to take the five-minute ferry ride to Jura. This little-inhabited island northeast of Islay is known for its untamed mountain landscapes and—no surprise—incredible whiskey. Another recommended option is to take a guided driving tour around Islay so you can glean as many details about the island as possible before you leave. 

Day 14: Islay to Glasgow & Depart

Sunset over the Isle of Skye's coast.
The early 20th-century Neist Point Lighthouse on the Isle of Skye

You'll head to the airport for the return flight to Glasgow in the morning. Then, at the appropriate time, you'll catch your connection home. This concludes your great Scottish adventure. Come back soon!

More Scotland Itineraries

Looking for more inspiration for your trip to Scotland? Check out these other Scotland itineraries, with outdoor adventures, cultural trips, and best-of tours to hit the highlights. 


Map of Hike Scotland's Highlands & Islands - 14 Days
Map of Hike Scotland's Highlands & Islands - 14 Days