Scottish Highlands & Islands 14-Day Trip Itinerary

Drive to Edinburgh

Begin your road trip by driving from Boston, Lincolnshire, north to Edinburgh.

Enjoy the changing landscapes as you cross the border into Scotland. Plan for comfort breaks along the way.

Check into Accommodation

Settle into your hotel in Edinburgh and take some time to refresh after your drive.

Royal Mile Stroll

Walk the historic Royal Mile, the main artery of Edinburgh's Old Town, connecting Edinburgh Castle to Holyrood Palace.

Soak in the medieval atmosphere, browse shops, and admire the historic buildings.

Edinburgh Castle Exterior

Enjoy views of Edinburgh Castle from outside.

Perched atop Castle Rock, it dominates the city skyline and offers fantastic photo opportunities, especially as the evening light begins to fall.

Dinner in Old Town

Dine at a traditional Scottish pub or restaurant in Edinburgh's Old Town, sampling local cuisine.

Edinburgh Castle Tour

Explore the historic Edinburgh Castle, home to the Scottish Crown Jewels, the Stone of Destiny, and St.

Margaret's Chapel. Delve into centuries of Scottish history.

Lunch in Grassmarket

Enjoy lunch in the lively Grassmarket area, known for its historic pubs and charming cafes.

Palace of Holyroodhouse

Visit the official residence of the King in Scotland.

Explore the historic apartments, the ruin of Holyrood Abbey, and the beautiful gardens. Focus on the history of Mary Queen of Scots.

Walk Arthur's Seat

Embark on a walk up Arthur's Seat, an ancient volcano and the main peak of Holyrood Park, offering panoramic views of Edinburgh and beyond.

Choose a path suited to your fitness level.

Wear comfortable walking shoes. The ascent can be steep in places.

Lind & Lime Gin Tour

Discover the craftsmanship behind Lind and Lime Gin with a distillery tour and tasting.

Learn about its unique balance of botanicals and enjoy samples.

Book online in advance.

Dinner in Leith

Enjoy dinner in the vibrant Leith area, known for its excellent restaurants and waterside setting.

Stirling Castle Visit

Drive from Edinburgh to Stirling and explore Stirling Castle, one of Scotland’s most historically important castles.

It was a favoured residence of the Stewart kings and queens.

Lunch in Stirling

Enjoy lunch in the historic town of Stirling, perhaps near the castle or in the city center.

Drive to Pitlochry

Continue your scenic drive north into the heart of Perthshire, heading towards the charming Victorian town of Pitlochry.

Pitlochry Exploration & Walk

Explore the picturesque town of Pitlochry.

Take a leisurely walk along the River Tummel, visit the famous Pitlochry Dam and Fish Ladder, or browse the local shops.

Blair Athol Distillery Tour

Experience a tour and tasting at Blair Athol Distillery, one of Scotland’s oldest working distilleries, located on the outskirts of Pitlochry.

Learn about the whisky-making process.

Dinner in Pitlochry

Enjoy dinner at one of Pitlochry's welcoming restaurants, many of which use local Scottish produce.

Drive to Inverness

Continue your journey north from Pitlochry to Inverness, the capital of the Highlands.

The drive offers beautiful scenery.

Urquhart Castle & Loch Ness

Visit the dramatic ruins of Urquhart Castle, set against the mysterious backdrop of Loch Ness.

Explore the castle's history and enjoy the stunning views over the loch, keeping an eye out for Nessie!

Loch Ness Cruise

Embark on a short boat cruise on Loch Ness from a nearby pier, offering a different perspective of the famous loch and the opportunity to learn more about its legends.

Lunch in Inverness

Head into Inverness city centre for lunch at a local cafe or restaurant.

Inverness City Walking Tour

Join a local walking tour of Inverness city centre with Cath, a local guide, to uncover its history, beautiful scenery, and local stories.

Booking: https://www.viator.com/tours/Inverness/Walk-Inverness-City-Centre-With-An-Experienced-Local-Guide/d5051-88768P1?mcid=42383&pid=P00266106&medium=api&api_version=2.0

Culloden Battlefield

Visit the poignant Culloden Battlefield, site of the final Jacobite Rising in 1746.

Explore the visitor centre and walk the battlefield to understand the tragic events.

Dinner in Inverness

Enjoy dinner in Inverness, the 'Capital of the Highlands,' with options ranging from traditional pubs to contemporary restaurants.

Drive to John o' Groats

Embark on a scenic drive along the A9 (part of the North Coast 500 route) towards the northern tip of mainland Scotland. Enjoy the dramatic coastal and mountain scenery.

Explore John o' Groats

Visit the iconic signpost at John o' Groats, signifying the end (or start) of mainland Britain.

Enjoy the coastal views and browse the local craft shops.

Lunch in Caithness

Have lunch in a local eatery near John o' Groats or along the coast, enjoying fresh local produce.

Duncansby Head & Stacks

Take a walk to Duncansby Head, the true north-eastern tip of mainland Britain, and admire the impressive sea stacks and dramatic cliffs.

This is an excellent spot for seabird watching.

Prime location for puffin spotting in June!

Drive to Gills Bay / Scrabster

Drive to your chosen ferry port (either Gills Bay for Pentland Ferries or Scrabster for NorthLink Ferries) for your crossing to the Orkney Islands the next day. Check into accommodation nearby.

Dinner near Ferry Port

Enjoy dinner in a restaurant near your accommodation, preparing for your early morning ferry to Orkney.

Scenic Highland Drive

Embark on a picturesque drive north through the dramatic Scottish Highlands, heading towards the northeast coast. Enjoy the ever-changing landscapes, from rolling hills to vast open moors.

There will be plenty of opportunities to stop for photos and stretch your legs at various viewpoints along the way. Grab a packed lunch or stop at a local cafe in a town like Aviemore or Inverness.

Dunrobin Castle & Gardens

Visit the magnificent Dunrobin Castle, the most northerly of Scotland's great houses, with its fairytale spires and formal gardens.

Explore the impressive interior and enjoy the daily falconry displays (check times upon arrival).

One of Scotland's grandest castles, offering beautiful gardens and fascinating history. Falconry displays are usually held twice daily.

Drive to Caithness

Continue your drive further north into the Caithness region, heading towards your overnight stop near the ferry departure points for Orkney (Scrabster or Gills Bay).

Dinner in Thurso

Enjoy a well-deserved dinner in Thurso, the most northerly town on mainland Scotland, before resting up for your island adventure.

Ferry to Orkney

Board the ferry from Scrabster to Stromness (approx.

1.5 hours) or Gills Bay to St Margaret's Hope (approx. 1 hour). Enjoy the sea views and look out for marine wildlife on your crossing to the Orkney Islands.

Book your ferry in advance, especially if taking a car. Check NorthLink Ferries (Scrabster-Stromness) or Pentland Ferries (Gills Bay-St Margaret's Hope).

Skara Brae Prehistoric Village

Step back 5,000 years at Skara Brae, a remarkably preserved Neolithic village unearthed by a storm.

Explore the ancient homes and learn about the lives of its early inhabitants.

Part of the Heart of Neolithic Orkney UNESCO World Heritage Site. Combine with a visit to Skaill House next door.

Ring of Brodgar & Stones of Stenness

Visit the majestic Ring of Brodgar, a huge Neolithic stone circle, and the nearby Stones of Stenness, both atmospheric remnants of Orkney's rich prehistoric past.

Enjoy a short walk around the sites.

Another key site within the Heart of Neolithic Orkney. Free to access.

Maeshowe Chambered Cairn

Discover the incredible Maeshowe, a Neolithic chambered cairn renowned for its sophisticated architecture and Viking runic inscriptions.

Access is via a guided tour from the visitor centre.

Book your tour slot well in advance, as places are limited. You'll be transported from the visitor centre to the cairn.

Check-in Kirkwall

Check into your accommodation in Kirkwall, Orkney's main town, and relax after a day of ancient exploration.

St Magnus Cathedral

Explore the magnificent St Magnus Cathedral in Kirkwall, a stunning example of Norse architecture, often referred to as the 'Light in the North'.

Free entry, but donations are welcome. Climb the tower for panoramic views (check availability).

Churchill Barriers & Italian Chapel

Drive across the Churchill Barriers, built during WWII to protect the naval base at Scapa Flow.

Visit the incredibly moving and ornate Italian Chapel, built by Italian Prisoners of War.

The Italian Chapel is a unique and poignant site. Free to drive over the barriers, small entry fee for the chapel.

Coastal Walk & Wildlife Spotting

Head to a coastal area like the Mull Head Nature Reserve or the cliffs around Yesnaby for a walk, enjoying the dramatic scenery and spotting seabirds (including puffins in June!

) and potentially seals in the waters below.

Bring binoculars! Puffins are usually present from April to early August. Be mindful of cliff edges.

Dinner in Kirkwall

Enjoy a final evening meal in Kirkwall, perhaps trying some fresh local seafood.

Ferry back to Mainland

Take the ferry back to the Scottish mainland from Orkney, either to Scrabster or Gills Bay.

Enjoy the final views of the islands from the sea.

Ensure you book your return ferry in advance. The timings can be flexible, allowing for a morning ferry.

North Coast 500 Scenic Drive

Begin your stunning drive along a section of the North Coast 500 route, heading west towards the rugged and beautiful landscapes of Sutherland and Wester Ross.

This is truly remote Scotland.

The roads are often single track with passing places, so take your time and enjoy the scenery. Stop frequently for photos.

Corrieshalloch Gorge National Nature Reserve

Take a short walk to the cantilevered bridge and viewing platform over Corrieshalloch Gorge, a spectacular mile-long canyon with a powerful waterfall.

Easy access from the main road. The bridge offers thrilling views of the falls and gorge below.

Arrive in Ullapool

Drive into the charming fishing village of Ullapool, a hub on the west coast, and check into your accommodation.

Ullapool Morning Stroll

Enjoy a leisurely morning walk around Ullapool harbour, watching the fishing boats and enjoying the views across Loch Broom.

Plenty of cafes for a morning coffee or breakfast.

Inverewe Garden

Discover the lush, subtropical Inverewe Garden, an oasis of exotic plants thriving against the odds on the rugged coast of Wester Ross, thanks to the Gulf Stream.

A National Trust for Scotland property. Features a wide variety of plants, a walled garden, and stunning views. Look out for red squirrels.

Wester Ross Coastal Drive

Continue your scenic drive through the breathtaking landscapes of Wester Ross, passing through picturesque villages like Gairloch and along stunning lochs and mountains.

Stop at viewpoints to soak in the dramatic scenery.

Eilean Donan Castle

Visit the iconic Eilean Donan Castle, arguably one of Scotland's most photographed castles, situated on an island where three sea lochs meet.

Explore its fascinating history and enjoy the picturesque setting.

Check-in Near Kyle of Lochalsh

Check into your accommodation near Kyle of Lochalsh, ideally positioned for your journey to the Isle of Skye tomorrow.

Drive to Isle of Skye

Enjoy a scenic morning drive from your previous overnight location (assumed Northern Highlands/Fort William area) towards the Isle of Skye, crossing the iconic Skye Bridge.

The landscapes will shift dramatically from rolling hills to rugged mountains and coastal views.

Eilean Donan Castle Photo Stop

Stop at the picturesque Eilean Donan Castle, one of Scotland's most iconic and photographed castles.

While an interior visit may be too time-consuming today, enjoy the stunning exterior views and take memorable photos.

There is a small visitor centre and shop, and public toilets are available.

Hike the Fairy Pools

Explore the enchanting Fairy Pools, a series of crystal-clear pools and waterfalls on the River Brittle.

Enjoy a moderate walk through the stunning Glen Brittle valley, with opportunities for paddling (if brave!) and beautiful photography.

Wear waterproof hiking boots as paths can be rocky and boggy. Parking is available for a fee (pay and display).

Dinner in Carbost

Enjoy a delicious dinner in the Carbost area.

Consider local seafood or traditional Scottish fare.

The Old Inn at Carbost or Oyster Shed (seasonal) are popular choices.

Hike the Old Man of Storr

Embark on a rewarding hike to the iconic Old Man of Storr, a dramatic rock pinnacle.

The path offers incredible panoramic views of the Trotternish peninsula and beyond.

Wear sturdy hiking shoes. The path can be steep in places. Parking is available (pay and display).

Kilt Rock & Mealt Falls

Visit the Kilt Rock viewpoint, where the basalt columns resemble the pleats of a kilt.

Witness the impressive Mealt Falls cascading directly into the sea below.

Explore The Quiraing

Drive through and take short walks around The Quiraing, a spectacular landslip known for its unique geological formations and breathtaking views. It's one of Skye's most dramatic landscapes.

The road can be narrow in places. There are various viewpoints and photo opportunities along the loop.

Portree Harbour Stroll

Return to Portree, Skye's charming capital.

Take a leisurely stroll around the colourful harbour, browse the local shops, and soak in the vibrant atmosphere.

Dinner in Portree

Enjoy a well-deserved dinner in one of Portree's many restaurants, offering a range of cuisines from traditional Scottish to contemporary European.

Consider making a reservation, especially on a Friday evening in June.

Scenic Drive to Oban

Embark on a beautiful drive from the Isle of Skye, crossing the Skye Bridge, heading south towards the coastal town of Oban. This route takes you past stunning lochs and through dramatic Highland scenery.

Drive & Walk in Glen Coe

Pass through the breathtaking Glen Coe valley, renowned for its spectacular mountain scenery and rich history. Stop at viewpoints to admire the Three Sisters of Glencoe and consider a short, easy walk to experience the raw beauty of the Highlands. Part of the iconic West Highland Way passes through here.

Numerous designated viewpoints with car parks. Dress warmly as it can be windy even in summer. The Glencoe Visitor Centre offers more information and facilities.

Oban Distillery Tour

Take a tour of the Oban Distillery, one of Scotland's oldest and smallest distilleries, nestled right in the heart of the town.

Learn about the whisky-making process and enjoy a tasting.

Booking in advance is highly recommended, especially on a Saturday. Minimum age for tasting is 18. Tours often run hourly. Estimated cost based on typical distillery tours.

McCaig's Tower Views

Take a short walk up to McCaig's Tower, Oban's Colosseum-like folly.

From here, you'll be rewarded with fantastic panoramic views over Oban town, the harbour, and across to the islands of Mull, Kerrera, and Lismore.

There's a steep walk up, but also a road for car access and parking near the top.

Seafood Dinner in Oban

Enjoy a delicious dinner in Oban, known as the 'Seafood Capital of Scotland.

' Indulge in fresh local catches.

Consider dining at Ee-usk or The Seafood Hut for excellent fresh seafood.

Staffa & Wildlife Boat Trip

Embark on an unforgettable full-day boat trip to Staffa Island.

Witness the incredible basalt columns of Fingal's Cave and, in June, observe the charming puffins nesting on the island. Many tours also include a stop at the Treshnish Isles for more seabird and seal spotting, and/or Iona for its historic abbey. This is a must for wildlife lovers!

This is a long day trip. Wear warm, waterproof clothing. Book well in advance. Tours often involve a ferry to Mull, a drive across Mull to Fionnphort, then the boat to Staffa. Check operator for exact itinerary and departure points. Puffins are typically present from April to early August.

Late Lunch / Early Dinner

Grab a quick, satisfying meal in Oban after your long boat trip before beginning your journey south.

Start Journey South

Begin your drive south from Oban towards central Scotland.

This evening's drive will take you through beautiful landscapes again, perhaps towards the Loch Lomond & The Trossachs National Park area or even further, depending on your preferred stopping point for the night.