Tailor-made Holiday · Scotland
Classic Scotland: Edinburgh, Inverness and Glasgow
Tailor-made, always
Every trip built from scratch around your dates, pace and preferences.
Your own specialist
One named person and a 24-hour number while you travel.
Hundreds of five-star reviews
Rated Excellent on Trustpilot across ten years of LGBTQ+ luxury travel.
At a glance
Scotland is a land of dramatic landscapes, historic cities, and age-old traditions, where heritage and modern elegance blend seamlessly. This carefully crafted itinerary takes you from the grand avenues of Edinburgh to the untamed beauty of the Highlands and the rugged shores of the Isle of Skye, offering the ideal blend of culture, adventure and indulgence that Scotland is renowned for.
Begin in Edinburgh, where the Royal Mile’s historic charm leads you through centuries of Scottish heritage. Step inside the iconic Edinburgh Castle, gaze upon the Crown Jewels, and listen to the echoes of the past within its stone walls.
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Venture beyond the city to Loch Lomond and Stirling Castle, where rolling hills meet medieval grandeur, and let the beauty of the Trossachs steal your breath. As you journey north, the legend of Loch Ness unfolds, and a tranquil boat cruise will take you past the mystical ruins of Urquhart Castle, standing as a silent witness to Scotland’s storied past.
The road to the Isle of Skye is one of Scotland’s greatest spectacles—a path carved through mountain peaks, glacial lochs, and deep glens. Arrive at Eilean Donan Castle, perched on its tidal island, before crossing the bridge to Skye’s untamed wilderness. Here, the towering Cuillin Mountains and sweeping sea views create a landscape that feels almost otherworldly, a place where myths still linger in the air.
The journey concludes in Glasgow, a city of architectural splendor and creative energy. Discover its Victorian landmarks, vibrant arts scene, and the legacy of Charles Rennie Mackintosh, before indulging in a refined afternoon tea at the historic Willow Tea Rooms.

Day by day
This is a sample plan, not a fixed departure. Days can be added, removed or reordered, and almost every client changes something. Prices are an entry-level guide; your quote will be exact.
Day 1: A Warm Scottish Welcome
Your journey begins with a seamless arrival, as a dedicated Meet & Greet assistant welcomes you at the airport. A private driver will transfer you to your stylish city retreat, where your Welcome Package awaits, ensuring a smooth and personalized introduction to Scotland.
Step out onto the Royal Mile, the historic spine of Edinburgh’s Old Town, where ancient buildings, whisky shops, and hidden closes reveal the city’s rich past. Follow our curated self-guided route, designed to uncover both renowned highlights and tucked-away treasures before heading to the gorgeous Market Street Hotel.
Day 2: Elegant Edinburgh
This morning, embark on a private walking tour with an expert guide, tracing Edinburgh’s centuries-old streets. Explore both the Old and New Towns, from Princes Street’s Georgian grandeur to the dramatic fortress of Edinburgh Castle. Stroll past St Giles’ Cathedral and uncover the secrets of the city’s underground vaults before stepping inside the castle to view the Crown Jewels of Scotland.
In the afternoon, savor a private whisky tasting at the Scotch Malt Whisky Society’s Kaleidoscope Bar, where a whisky expert will introduce you to the finest drams Scotland has to offer. A gourmet meal rounds off your experience in true Scottish style before you return to your hotel to rest.
Day 3: Wild Scottish Beauty
Venture beyond the city on an intimate small-group tour to explore Scotland’s stunning natural landscapes. Stop at the Kelpies Monument, two colossal steel horse heads honoring Scotland’s industrial heritage, before heading into The Trossachs National Park—a breathtaking expanse of forests, mountains, and shimmering lochs.
Pause at the tranquil shores of Loch Lomond, where you may follow part of the West Highland Way, retracing the steps of Scottish folk hero Rob Roy. Then, journey to the majestic Stirling Castle, the former royal stronghold that played a crucial role in Scotland’s history. Choose to explore its grand halls and sweeping battlements before returning to Edinburgh in the late afternoon.
Day 4: Highlands and Scottish Legends
Board a scenic train to Inverness, the gateway to the Highlands, where a private driver awaits to transfer you to your hotel.
This afternoon, set out on a Loch Ness adventure, first by coach, tracing the loch’s legendary shores, before embarking on a tranquil boat cruise. Stop at the evocative Urquhart Castle, where medieval ruins overlook the inky waters of the loch, steeped in mystery and myth.
As evening falls, immerse yourself in the tales and traditions of the Highlands with an exclusive whisky and storytelling experience. Savor the region’s finest single malts while a master storyteller recounts ancient legends and Highland folklore, accompanied by the lilting strains of traditional music. Journey to Kingsmills Hotel to recuperate in the evening.
Day 5: The Isle of Skye
Today’s small-group journey takes you into the most breathtaking landscapes of Scotland, as you drive along the shores of Loch Ness toward the wild beauty of the Isle of Skye.
Pause at Invermoriston, where an ancient stone bridge spans a tumbling waterfall, before continuing past the Five Sisters of Kintail, a dramatic mountain range cloaked in legend. Stop at the spectacular Eilean Donan Castle, perched on a tidal island at the confluence of three lochs. Choose to explore the castle’s medieval halls before continuing onto Skye’s rugged terrain.
Drive through Glen Suardal and the Red Cuillin Hills, soaking in the otherworldly landscapes, before arriving at Elgol, a remote fishing village with breathtaking views of the Black Cuillin mountains and the wild Atlantic beyond.
Return to Inverness via the scenic Black Isle, passing through windswept Highland countryside, back to Kingsmills Hotel.
Day 6: Whisky, Industry and Heritage in Glasgow
Travel by train to Glasgow, a city that has transformed from an industrial powerhouse to a cultural capital. Upon arrival, an expert guide leads you on an immersive journey into whisky-making, beginning with the Dockside Story, where you’ll uncover the city’s deep-rooted connections to Scotland’s national drink. Step behind the scenes at Clydeside Distillery, where you’ll witness the craftsmanship behind pure new-make spirit, before sampling an exceptional range of Glasgow’s finest whiskies.
In the afternoon, visit the Kelvingrove Art Gallery & Museum, home to masterpieces by Dalí, Rembrandt, and the Glasgow Boys, along with a whimsical floating heads installation that captures the city’s creative spirit.
Enjoy a cozy stay at the Dakota Glasgow.
Day 7: A Cultural Escape
Glasgow’s vibrant streets are best explored on foot, and today, your private guide will introduce you to the city’s architectural treasures and creative energy. Walk through Merchant City, a district of former tobacco barons and tea traders, now home to boutique shops and gourmet cafés. Discover the elegant Buchanan Street, home to Scotland’s finest shopping and historic theaters, before tracing the city’s evolution through its Victorian, Art Nouveau, and modernist landmarks.
In the afternoon, indulge in a quintessentially Scottish afternoon tea at the Willow Tea Rooms, designed by the legendary Charles Rennie Mackintosh. Enjoy delicate finger sandwiches, warm scones with clotted cream and jam, and exquisite pastries, served in an elegant Art Nouveau setting that transports you to Glasgow’s golden age.
Enjoy your final evening in Scotland at the Dakota Glasgow.
Day 8: A Fond Farewell
Your journey through Scotland’s breathtaking landscapes and cultural riches comes to an end as a private driver transfers you to the airport, ensuring a seamless departure.
Our Experts
I'm Scottish so am very fond of this country. Windswept Highlands landscapes, stunning lochs, mountains and glens... it's a paradise for those who love dramatic scenery.
The cities of Scotland have an energy that isn't seen anywhere else on earth. Welcoming, vibrant, and with that famous Scottish sense of humor. Edinburgh is a must-see for those visiting this beautiful country.
Stellar service. Stellar products. Stellar people and it gets so much better when you pick up the phone and call.
Anthony S.
Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.
John
I’m confident in giving Out Of Office a 5-star review! They are one of the leaders in this space without a doubt.
Tiberiu
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Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specialising in tailor-made holidays and extraordinary journeys around the world. We create bespoke luxury holidays, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalised experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with travelling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveller, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalised service and discretion.
Do you create tailor-made LGBTQ+ holidays?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalised itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travellers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of travelling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
One named specialist, first enquiry to homecoming. No call centre, and nothing is charged until you decide to book.