Hiking Scottish Highlands and Islands with Heather Thomson

Prepared with pleasure exclusively for Heather Thomson

Friday 9th May – Friday 16th May 2025

Number of Travellers: 8
Duration: 8 Days / 7 Nights


Hiking Scottish Highlands and Islands with Heather Thomson

Group size: Up to 8 travelers (which includes 2 x HT Tour Leaders FOC)

Trip Highlights

  • Enjoy guided hikes in the Scottish Highlands and islands, including Loch Lomond National Park and the west coast.
  • Discover Scotland’s rich heritage and culture with visits to castles, a whisky distillery, and through stories shared by our guide on the hikes.
  • Explore the country’s capital city, Edinburgh – a UNESCO World Heritage Site.


This itinerary starts in Glasgow and finishes in Edinburgh, both cities are easily accessible by air and mainline trains. We’ll hike through varied landscapes of the Scottish Highlands with our experienced guides, taking in the mountains and glens of Loch Lomond National Park before exploring Scotland’s island-fringed coastlines. Along the way, we’ll have various cultural experiences visiting an ancient castle, a wildlife-themed boat cruise, visiting a Highland whisky distillery and exploring Edinburgh’s historic Old Town.

Note – Hikes will typically range from 2-5 hours.


Start / Finish – Glasgow / Edinburgh 

Both Glasgow and Edinburgh are easily accessible, connected by regular flights from various cities in the UK and Europe, as well-as some direct flights from the US. They are also on the UK mainline rail network, with the sleeper train being an attractive option for the journey to/from destinations in the south of the UK. The airports are just 20 minutes from the city center and is connected by bus and taxi.

Day by Day

Day 1 - Friday 9th May - Arrival in Glasgow

Meeting in Glasgow early afternoon, we leave the city and head north into the Scottish Highlands. We break the journey to visit the William Wallace monument, a landmark that tells the story of the patriot and martyr who became Scotland’s national hero (his story told in the movie, Braveheart). We then continue onwards and enjoy a leisurely check-in to our hotel, an 18th-century converted alehouse overlooking the village green in the sleepy village of Drymen.

Overnight: The Winnock Hotel, Drymen, Loch Lomond 

Meals included: Dinner

Total transfer time: c. 1.30 hrs by private transfer.

NB. Optional pre-night accommodation can be provided. 

Day 2 - Saturday 10th May - Hiking Conic Hill

Today we have our first trek with a classic hike up an easy peak offering unbeatable scenery over Loch Lomond. Conic Hill is a small summit (358m high) with an almighty view and is a part of the West Highland Way. The view across Loch Lomond from the summit is one of the best in Scotland. Afterwards, enjoy a celebratory drink before returning to our hotel, where the rest of the afternoon and evening is free for you to perhaps go for a spa treatment and then enjoy one of the local restaurants of your choice.

Hike details: 6km, 400m of ascent, approx 3-4 hours hiking

Overnight: The Winnock Hotel, Drymen, Loch Lomond

Meals included: Breakfast, Packed Lunch (Dinner not included)

Total transfer time: c. 30mins each way by private transfer.

Day 3 - Sunday 11th May - Visit Inveraray Castle and Kilmartin Glen

After breakfast, we set off for the west coast. At the head of Loch Fyne, we visit Inveraray castle, the seat of the Clan Campbell. Later, we’ll stop for a walk through Kilmartin Glen, one of the finest concentrations of neolithic and bronze age sites in Scotland. This is an easy hike between Kilmartin Castle and Nether Largie which connects several ancient burial cairns and standing stones. Afterwards, a 15 minute drive takes us to our hotel, which boasts one of the finest views in Scotland from its dining room.

Hike details: 3.5km, 50m of ascent, approx 1-1.5 hours hiking

Overnight: Loch Melfort Hotel, Arduaine, near Oban

Meals included: Breakfast, Cafe Lunch, Dinner

Total transfer time: c. 2.30 hrs by private transfer.

Day 4 - Monday 12th May - Enjoy a wildlife sea adventure

This morning, we take a boat trip to explore the local coastline and seek out wildlife. We hope to see a variety of wildlife such as porpoises, dolphins, otters, sea eagles and maybe even whales; while being entertained with stories of viking legends, Celtic Saints and local shipwrecks. We’ll also see the spectacular Corryvreckan Whirlpool, one of the largest in the world (viewed from a safe distance!!). Back on dry land, we explore the tiny island of Easdale, home of the world stone-skimming championships, before returning to the hotel to relax and freshen up before dinner.

Hike details: Short walk only, approx 1 hour of easy walking

Overnight: Loch Melfort Hotel, Arduaine, near Oban

Meals included: Breakfast, Cafe Lunch, Dinner

Total transfer time: c. 45mins each way by private transfer.

Day 5 - Tuesday 13th May - Hike around the Isle of Kerrera

This morning we will board a small passenger ferry and make the short crossing to the peaceful Isle of Kerrera, where we will enjoy a 10km circuit of the island. Despite its small size, the island has a rich history featuring kings, castles and feuding Highland clans, mostly centered around Gylen Castle, which dates back to the 16th century. As we hike, enjoy incredible vistas across the Sound of Kerrera, with views towards Mull, Jura and the Garvellachs. Back on the mainland, we transfer east to Perthshire, where we will check-in to our hotel, located in the pretty Victorian town of Pitlochry.

Hike details: 11km, 275m of ascent, approx 4-5 hours hiking

Overnight: Acarsaid Hotel, Pitlochry

Meals included: Breakfast, Packed Lunch, Dinner

Total transfer time: c. 2.30 hrs by private transfer.

Day 6 - Wednesday 14th May - Hiking Ben Vrackie

Perthshire is renowned for its rich variety of scenery. Every Highland village has a mountain it describes as its own, and Pitlochry’s mountain is Ben Vrackie, which towers over the village. The hike takes us across the moors to a small loch before we take on the steep final slopes to the summit, where we are rewarded with wonderful views*. Descending to Pitlochry, we visit a local whisky distillery for a tour with tasting. The evening is free for you to explore the village and its restaurants.

Hike details: 10km, 800m of ascent, approx 4-5 hours hiking

*Note – hikers can opt to stop at the small loch and miss out the final summit climb, making the route an easier hike

Overnight: Acarsaid Hotel, Pitlochry

Meals included: Breakfast, Packed Lunch (Dinner not included)

Day 7 - Thursday 15th May - Walking tour of Edinburgh's historic Old Town

After breakfast we travel south to Edinburgh, where we head out for a day spent exploring the beautiful cobblestone streets of the city. Full of history, the capital is very accessible by foot. Wander up the Royal Mile, stopping to visit the architecturally stunning St Giles Cathedral, and enjoy panoramic views from Edinburgh Castle. Pick up a coffee and a pastry from one of the wee artisan shops, dipping into local galleries, cheesemongers and bookshops. Afterwards, take some free time to shop for souvenirs, explore further, or simply immerse yourself in the vibrant, cosmopolitan capital.  Tonight, we gather to enjoy a farewell dinner under the twinkling lights of the city and to celebrate our adventure together.

Overnight: Bruntsfield Hotel, Edinburgh

Meals included: Breakfast, Cafe Lunch, Dinner

Day 8 - Friday 16th May - Depart Edinburgh

After breakfast the trip ends at 11.30. Guests can be dropped off at the airport or trainstation.

For those that are staying for a post-night, there is the opportunity in the afternoon to meet with a genealogist, or visit a spa for a treatment (to be booked in advance and at an additional cost).


Hike details: No hiking today

Meals included: Breakfast

NB. Optional post-nights accommodation can be provided. 

Trip Details

Inclusions Read More
  • A free place each for 2 x Heather Thomson Tour Leaders sharing in a twin room
  • 7 nights accommodation in small hotels
  • Breakfast each day
  • 6 lunches – either cafe lunch or packed lunches (Day 1 and Day 8 not included)
  • 5 evening meals (Days 2 and 6 not included)
  • Additional snacks while hiking
  • The services of qualified and experienced guide from Day 1 to Day 8
  • All transfers as required from Day 1 to Day 8, starting in Glasgow and finishing in Edinburgh
  • All guided hikes, as well as activities mentioned in the itinerary, specifically:
    • Day 1 – William Wallace monument
    • Day 3 – Visit to Inveraray Castle, Dunadd and Kilmartin Glen
    • Day 4 – Wildlife boat cruise and visit to Easdale Island
    • Day 6 – Whisky distillery tour with tasting
    • Day 7 – Walking tour of Edinburgh
  • Gratuities for hotel staff and restaurant staff
  • Trip design and delivery
  • 24/7 in-country trip support
Exclusions Read More
  • Meals not mentioned in the inclusions
  • Activities and entrance fees not mentioned in the inclusions
  • Flights
  • Travel insurance
  • Gratuities for the guides
Arrival & Departure Read More

Your guide will meet you at Glasgow at 1:00 pm on the first day of your trip.

You will be returned to Edinburgh at 11:30 am on the final day of your trip.

Pricing Read More

The NET price for this itinerary is variable depending on group size as follows:

  • 5 – 6 guests: £3,700pp (trip confirmed on min. 5 guests)
  • Includes free places for 2 x HT Tour Leaders (8 x travelers in total)
  • Single supplement: £750 (2 single occupancy rooms available)


  • Pre-night option in Glasgow – 1 x pre-night (May 8th) – Hotel Indigo (or similar) – £250 per room per night for twin occupancy or £240 per night for single occupancy – TBC
  • Post-night option in Edinburgh – 1 x post nights (May 16th) – Bruntsfield Hotel (or similar) – £275 per room per night for twin occupancy or £250 per night for single occupancy – TBC


Please also see the Partner Agreement for terms and conditions about the running of this itinerary. To follow.

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