Leonard's Scottish Adventure v2

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 West Coast and back

Day by Day

Day 1 - Monday 18th August - Welcome to Scotland! Meet Your Guide & Head North

On arrival at the airport you will be met by your private Highlands guide (who will also act as your driver for your days together). Together you will head north to start your explorations, heading to the Kingdom of Fife full of history & picturesque coastal scenery.

Maybe hike part of the Fife Coastal Trail along the “Fringe Of Gold”, as the Fife beaches are known, and through traditional villages which are built around tiny fishing harbours. These are all wonderfully picturesque with wee stone houses keeping watch over the brightly painted fishing vessels in the harbours, so make sure that you have your camera handy. Don’t forget to stop along the way and celebrate your walk with the local’s favourite traditional (and award-winning) Fish & Chips. 

Explore the characterful university town of St Andrews, more recently the Duke and Duchess of Cambridge famously met during their studies here but it is full of history and stories. However, St Andrews is much better known for being the ‘birthplace of golf’ and you will be able to see the greens of the famous ‘Old Course’. 

This day is flexible and your guide will personalise it depending on your interests and share some of their favourite hidden gems with you as you explore. Then continue north towards your welcoming hotel.

Note: Explorations & Lunch are dependant on a morning arrival time.

Overnight: Pitlochry | Fonab Castle Hotel
Room Type: Woodland Lodge Superior
Meals Included: Lunch

Day 2 - Tuesday 19th 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: Woodland Lodge Superior
Meals Included: Breakfast and Lunch

Day 3 - Wednesday 20th August - Glencoe - Hiking & Legends

This morning you make your way west to immerse yourselves in the rugged mountain landscape there. 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 fabulous hiking options to suit every level of energy and challenge. After your hike settle down with a celebratory beverage in a traditional climbers pub and listen to local legends and fascinating tales of the dark past of Glencoe told by a local storyteller.

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

Day 4 - Thursday 21st August - Explore the 'Road To The Isles'

Today you will explore 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 before heading back to your hotel in Glencoe.

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

Day 5 - Friday 22nd August - South To Edinburgh

Bid farewell to the Highlands this morning as your guide takes you south to Edinburgh. 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 on arrival. The choice is yours. Your guide will bid you farewell here, leaving you to enjoy the rest of the day at your own pace.

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

Day 6 - Saturday 23rd 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 7 - Sunday 24th August - Free Day to enjoy the Festival - Late Afternoon Underground Streets Tour

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!

Late afternoon you will discover yet another side of Edinburgh as you adventure down underneath Edinburgh on an underground tour of a warren of tiny fascinating streets dating from the 17th century. Hear the tales of the lives of the residents and immerse yourselves in the past.

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

Day 8 - Monday 25th August - Full Free Day to Self-Explore & enjoy the Festival

Today is free to visit some of Edinburgh’s wonderful attractions independently; maybe enjoy the calm of the serene Botanic Gardens, explore the charming village of Dean or go aboard the Royal Yacht Britannia, once the floating palace of Queen Elizabeth II and The Duke of Edinburgh. The choice is yours.

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

Day 9 - Tuesday 26th August - Fly to London

This morning a private transfer will take you to Edinburgh Airport to catch your flight down to London. On arrival a private driver will meet you and transfer you to your hotel. Depending on your arrival time you can drop your bags and head out to start exploring, or check in and choose to relax at the hotel.

Overnight: London | The Marylebone
Room Type: Deluxe Queen
Meals Included: Breakfast

Day 10 - Wednesday 27th August - Hidden Highlights Of London

Enjoy a full day with an expert local city guide today with an infectious passion for the quirky and offbeat, leads you through narrow alleys and hidden corners that whisper secrets of centuries past.. The itinerary is flexible and will be led by your interests, but you are sure to discover many fascinating sites as your guide shares the hidden gems of this complex city with you.

Your guide will point out peculiarities that escape the casual observer – a historic pub with a resident ghost, a street artist painting a vivid mural, and a quaint bookstore tucked away in a cobblestone lane. You find yourself immersed in a world of eccentricities, where every turn reveals a new, delightful surprise. The guide’s stories weave a tapestry of London’s eccentric history, making you feel as though you’re walking through the pages of a novel. With every step, you become enchanted by the city’s charm and the guide’s enthusiasm, forging memories that will linger long after the day is over.

Overnight: London | The Marylebone
Room Type: Deluxe Queen
Meals Included: Breakfast

Day 11 - Thursday 28th August - Quirky Foodie Tour & West End Extravaganza

Embark on a sumptuous food and drink journey in one of London’s most famous markets with a characterful private foodie guide.  Spend your morning savouring some of the finest British delicacies, while enjoying the unique setting and vibrant atmosphere. After having delighted your taste buds and enchanted your senses, the rest of the day is free for you to enjoy as you wish. Maybe take the free afternoon to relax at your hotel, or visit one of the world-renowned galleries or quirky museums in town. Then finish your day with a captivating performance of a big show in London’s famous West End theatre district.

Overnight: London | The Marylebone
Room Type: Deluxe Queen
Meals Included: Breakfast

Day 12 - Friday 29th August - Free Day to Self-Explore

You have the full day free to day to continue your explorations at your own pace, maybe using tips from your private guides of the last couple of days. Soak in the cosmopolitan street mix and enjoy the unique shopping opportunities.

Overnight: London | The Marylebone
Room Type: Deluxe Queen
Meals Included: Breakfast

Day 13 - Saturday 30th August - Depart

A private transfer will collect you from your accommodation and take you to Heathrow  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 1 to Day 5
  • All transfers in a private vehicle driven by our guide on guided days
  • Airport Transfer on Arrival Day, includes Meet & Greet
  • Airport Transfer to Edinburgh Airport on Day 9
  • Airport Transfer on Arrival in London Heathrow on Day 9, includes Meet & Greet
  • Airport Transfer to London Heathrow on Departure Day
  • All guided hikes mentioned in the itinerary
  • Entrance fees and activities mentioned in the itinerary, specifically:
    • Entry Fees in Fife as per interest – D1
    • Private Storyteller Experience in Glencoe
    • Private Morning Walking Tour in Edinburgh with Expert Local City Guide
      • Includes entry to Edinburgh Castle
    • Edinburgh Military Tattoo Tickets – Premium Seats
    • Entry to public Tour of Underground Streets
    • Private Full Day Walking Tour in London with Expert Local City Guide
      • Includes 3 x Entry Fees as per interest
    • Private Foodie Tour with Chubby Fellows – Fine British Fodder (approx 2.5hrs)
    • Tickets for West End Show (tbc on availability and client interest)
      • Best Seats Available in The Stalls
  • 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.