Leonard's Scottish Adventure

Monday 18th August – Saturday 30th August 2025

Number of Travellers: 2
Duration: 13 Days / 12 Nights


  • Discover the hidden gems and local's favourites with your experienced private guide
  • Hike in some of the most beautiful landscapes in Scotland
  • Breathe in the fresh air of remote glens and sweeping silver beaches as you explore from the Highlands to the islands and back

Day by Day

Day 1 - Monday 18th August - Welcome to Scotland

On arrival at the airport you will be met by a private driver who will transfer you to your city centre hotel. Depending on your arrival time you can choose to relax at the hotel or head out to start exploring this unique city.

Overnight: Edinburgh | The Raeburn
Room Type: Deluxe Double
Meals Included: None

Day 2 - Tuesday 19th August - Historic Edinburgh & Military Tattoo Experience

Spend the morning exploring the tales of the cobbled streets and alleyways of Edinburgh’s historic Old Town on a private walking tour with an expert local city guide. You will visit some of the famous sights as well as discovering some fascinating lesser known gems. This afternoon is free for you to continue exploring at your own pace, maybe using some tips from your guide before a special evening ahead.

The Edinburgh Military Tattoo is a world-renowned outdoor performance that started in 1950. It is different every year and is staged on the castle esplanade with incredible views over the city. The show ends with a spectacular fireworks display and is sure to blow you away.

Overnight: Edinburgh | The Raeburn
Room Type: Deluxe Double
Meals Included: Breakfast

Day 3 - Wednesday 20th August - Free Day to Self-Explore & enjoy the Festival

The streets of Edinburgh will be buzzing with energy due to the various festivals running this month and you will pass street performers and entertainment on every corner as you explore. Follow your curiosity through the twisting cobbled streets of the Old Town and enjoy the vibrant ambience. There will be a huge variety of different shows and concerts to choose from if you wish to catch a performance or three!

Overnight: Edinburgh | The Raeburn
Room Type: Deluxe Double
Meals Included: Breakfast

Day 4 - Thursday 21st August - Meet your Private Guide & Head North via Kingdom of Fife & St Andrews

This morning your Private Guide (who will also act as your driver) will meet you at your hotel and together you will head north towards the Highlands via  the Kingdom of Fife and historic city of St Andrews. Hike along the Fife Coastal Trail and hear the history of the charming fishing villages from your guide, or explore this characterful university town full of history and stories. More recently the Duke and Duchess of Cambridge famously met during their studies here but St Andrews is known for being the ‘birthplace of golf’ and you can see ‘The Old Course’ spread out along the coastline.

Overnight: Pitlochry | Fonab Castle Hotel
Room Type: Castle Signature
Meals Included: Breakfast and Lunch

Day 5 - Friday 22nd August - Hiking & Exploring Locally with your Guide.

You have the full day to explore the surrounding mountains and glens on foot today and you will be spoilt for choice with all the possible routes. Together with your guide you will decide on an option which suits your preferred level of challenge (and energy!), and the weather. Maybe conquer a local summit for fabulous views, or enjoy a gentle atmospheric exploration to discover a waterfall or forest walk. No matter what you pick, your guide will make the landscape come alive with stories and local insights. Fingers crossed for a scheduled performance in the award winning local theatre tonight for a perfect finish to the day.

Overnight: Pitlochry | Fonab Castle Hotel
Room Type: Castle Signature
Meals Included: Breakfast and Lunch

Day 6 - Saturday 23rd August - North To Inverness & Fly Fishing Afternoon

Transfer North through the Drumochter Pass and the edge of the Cairngorms national Park today. Breaking your travels to enjoy a private fly fishing experience at a quiet loch with an expert local fisherman. Spend the afternoon immersing yourselves in the techniques and lovely location with the added benefit of specific insider knowledge. Then your guide will take you to settle into your welcoming hotel.

Overnight: Inverness | Kingsmills Hotel
Room Type: Patio Room
Meals Included: Breakfast and Lunch

Day 7 - Sunday 24th August - Transfer To Skye via Rewilding Forest & Eilean Donan Castle

Transfer to Skye, stopping to visit and hike at the fascinating rewilding centre & passing Loch Ness & Eilean Donan castle along the way

Enjoy some fabulous scenery as you make your way to Skye today through steep sided mountain glens on the way, and past the deep water of secretive Loch Ness (keep your eyes peeled for ‘Nessie’). Stop to discover the joyous rewilding work which is being done on the slopes north of the loch as you walk the forest trails. You may also want to explore the elegant Eilean Donan castle, set out on the water on a private island and surrounded by majestic scenery. Your guide will then take you onwards, passing over the graceful arc of the Skye Bridge onto ‘the misty isle’ itself and carrying on to your welcoming hotel.

Overnight: Isle of Skye | Cuillin Hills Hotel
Room Type: Standard Double
Meals Included: Breakfast and Lunch

Day 8 - Monday 25th August - Hiking & Exploring Skye

Today you have a full day to explore some of the special corners of this magical island with your guide. You will be spoilt for choice with fascinating history and dramatic landscape on offer, with unique hiking routes through stark and unusual rock formations and sweeping coast and mountain views to enjoy in almost every direction. This ‘misty isle’ is also home to so many curious stories and legends of fairies and islander culture, your guide will share some of the best hidden gems and personalise the day to your interests. Although we highly suggest heading to the secretive Loch Coruisk at the foot of the Black Cuillin Mountains, a truly special experience.

Overnight: Isle of Skye | Cuillin Hills Hotel
Room Type: Standard Double
Meals Included: Breakfast and Lunch

Day 9 - Tuesday 26th August - Discovering More of Skye & Afternoon Wildlife Boat Trip

Take a hike out to one of the more spectacular rock formations this morning and enjoy the incredible views as you explore with your guide. Set out from Portree harbour this afternoon to get a different perspective on the island as you explore the picturesque Sound of Raasay by boat. Admire the mountain vistas, sea cliffs and caves, which are home to a wide variety of seabirds and other wildlife. Look out for sea eagles, dolphins, seals and even whales, as well as the lively seabird communities.

Overnight: Isle of Skye | Cuillin Hills Hotel
Room Type: Standard Double
Meals Included: Breakfast and Lunch

Day 10 - Wednesday 27th August - Return To The Mainland & 'Road To The Isles'

After taking the short ferry back to the mainland you’ll travel along the stunning Road to the Isles with your guide. This is frequently listed as one of the most beautiful drives in the world and it is easy to see why. Admire the silver sand beaches of Arisaig and admire the views back to Skye and out to the small isles. Pass the Glenfinnan Viaduct, which you may well recognise from the Harry Potter films. Hear the tales of the Glenfinnan Monument and see if you can spot the Jacobite Steam Train puffing its way along the tracks. Then continue onwards to your unique hotel in Glencoe.

Overnight: Glencoe | Kingshouse Hotel
Room Type: Feature King
Meals Included: Breakfast and Lunch

Day 11 - Thursday 28th August - Hiking Glencoe

The dramatic mountains and ridges of Glencoe have featured as the backdrop in many films and once you are looking up at these summits it is easy to see why! Today you will explore this famous valley with your guide, there are plenty of options to suit every level of energy and challenge. After your hike settle down with a celebratory beverage in a traditional climbers pub for a perfect finish to the day.

Overnight: Glencoe | Kingshouse Hotel
Room Type: Feature King
Meals Included: Breakfast and Lunch

Day 12 - Friday 29th August - South To Glasgow

Bid farewell to the Highlands this morning as your guide takes you south to Glasgow. You have the option to fit in one last hike in this rugged landscape, or you could choose to arrive in the city earlier so you have more time to explore. The choice is yours.

Overnight: Glasgow | Hotel Du Vin, Glasgow
Room Type: Deluxe Double
Meals Included: Breakfast and Lunch

Day 13 - Saturday 30th August - Depart

A private transfer will collect you from your accommodation and take you to Glasgow airport to make your onward connections. Waving farewell for now but taking with you special memories and wonderful stories of your explorations.

Meals Included: Breakfast

Trip Details

Inclusions Read More
  • 12 nights accommodation, as stated in the itinerary above
  • Most meals, as stated in the itinerary above
  • The services of a qualified and experienced guide from Day 4 to Day 12
  • All transfers in a private vehicle driven by our guide on guided days
  • Airport Transfer on Arrival Day, includes Meet & Greet
  • Airport Transfer on Departure Day
  • All Ferry Travel Included in the Itinerary
  • All guided hikes mentioned in the itinerary
  • Entrance fees and activities mentioned in the itinerary, specifically:
    • Private Morning Walking Tour in Edinburgh with Expert Local City Guide
      • Includes entry to Edinburgh Castle
    • Edinburgh Military Tattoo Tickets – Premium Seats
    • Private Afternoon Fly Fishing Experience
      • Includes expert fishing guide, and all required equipment
    • Entry to Eilean Donan Castle
    • 2 x Entry Fee on Skye as per interest
    • Wildlife Boat Trip
  • Personalised trip design and delivery
  • 24/7 In-Country Support from the Wilderness Team
Exclusions Read More
  • Internal & International Flights
  • Travel insurance
  • Meals not mentioned in the inclusions
  • Activities and entrance fees not mentioned in the inclusions
  • Gratuities for the main driver guide
Notes Read More
  • All suggested accommodations and services are subject to availability at the time of booking
  • A 20% deposit is required before any accommodation and services will be confirmed
  • This quote is valid for 14 days from the date quoted, after this time pricing may be subject to revision
  • Activities are only private is specifically stated
Optional Upgrades Read More
  • Room Upgrades are avvailable in some locations, subject to availability. Pricing on request.
  • Edinburgh Military Tattoo – Upgrade to Premium Package Experience. Pricing on request.
Terms & Conditions Read More

Please see our booking terms here.


The Raeburn

112 Raeburn Place | Edinburgh |
EH4 1HG | Scotland
Phone: +44 (0)131 332 7000
Web: theraeburn.com

Fonab Castle Hotel

Foss Road | Pitlochry | Perthshire |
PH16 5ND | Scotland
Phone: +44 (0)1796 470140
Web: fonabcastlehotel.com

Kingsmills Hotel

Culcabock Road | Inverness | Highland |
IV2 3LP | Scotland
Phone: +44 (0)1463 237 166
Web: kingsmillshotel.com

Cuillin Hills Hotel

Portree | Isle of Skye |
IV51 9QU | Scotland
Phone: +44 (0)147 861 2003
Web: cuillinhills-hotel-skye.co.uk

Kingshouse Hotel

Glencoe | Ballachulish |
PH49 4HY | Scotland
Phone: +44 (0)1855 851 260
Web: kingshousehotel.co.uk

Hotel Du Vin, Glasgow

1 Devonshire Gardens | Glasgow |
G12 0UX | Scotland
Phone: +44 (0)141 378 0385
Web: hotelduvin.com/locations/glasgow