13 minute read
Dream Escape's 20th anniversary: A Celebration of Curiosity and Adventure
As Dream Escape reaches its 20th anniversary year, founders Holly Mackie and David Tobin celebrate by sharing their start-up secrets and the fascinating stories and memories they’ve collected along the way.
Our starting point was a partners’ desk, a website and no idea,” reminisces Holly about first launching Dream Escape together with David in 2005. Now, two leading voices in the luxury travel community, the pair have accrued 20 years of experience. They’ve brought together a team of over 20 experienced creative planners and travel professionals – all waiting to plan incredible trips for clients across the world.
The 20th milestone also coincides with David and Holly’s 20th wedding anniversary, and has prompted them to reflect on their personal and professional journey across the last two decades.
Throughout this year, Dream Escape will be sharing more of David and Holly’s stories by launching a celebratory book, delving deeper into the people, places and philosophy that make the brand so unwaveringly unique –available in summer 2025.
Where it all began... “The anniversary creates an opportunity for us to pause and thank so many people in the travel industry who believed in and supported us from the early days,” says Holly. “It’s the perfect time to recognise where we’ve got to and where we can go!”
The brand started with the couple effectively turning their lives upside down, driven by passion and a clear vision. “Back in 2005, I was a board director in London and the idea of quitting your job and doing something different was obscene – certainly to my mother, who was horrified,” explains David.
“We left our jobs and got married on 21 May 2005. We took a six-week honeymoon and then came back to our new home in Scotland. I remember us sitting at this big desk opposite each other with two computers, a URL (dreamescape.co.uk, of course) and no idea what we were going to do,” he says, laughing.
“Our move to Scotland opened our eyes to what an incredible country it is and the opportunities that were within,” says Holly. “We were also fuelled by a desire to be our own bosses and create something we 110% believed in.
“David wrote a business plan in about 20 minutes. I’d reached out to Scottish Enterprise for support and a lovely contact had told me that I needed to hurry and submit an application – this was for a tiny grant for anyone under 30 looking to start a business. We had no experience in travel, other than travelling ourselves,” she says.
While launching the brand in the early days, David and Holly also undertook an ambitious house renovation, had children and later moved to the British Virgin Islands. “It’s not the most traditional route for starting a business,” says David. “You wouldn’t find it in a Harvard Business Review!”
The rest is history, so to speak, but one thing is certain – creating Dream Escape was no easy feat. The brand has stood strong through bumps in the road, including the financial meltdown in 2008 and more recently the pandemic. “It’s a triumph of stamina, if I’m honest,” says David.
“We knew that 90% of business startups fail and so we needed to channel a lot of drive and perseverance,” agrees Holly. “It was helpful to surround ourselves with experienced people, but it was a steep learning curve and we made mistakes along the way. Now we know you have to make them to progress.
“We’re established now and we can come in with confidence and say we have a business that’s 20 years old – we’re also proud to remain privately owned. We’ve taken everyone on the journey with us, and now we want to pass on that experience and knowledge to other people,” she says.
In addition, both founders have channelled their passion into supporting local and national charities along the way – from donations and volunteering to David’s recent sponsored bike ride along the North Coast 500 for Cancer Research.
Fuelled by curiosity
Another reason for Dream Escape’s roaring success is its dedication to unearthing new, awe-inspiring experiences. “We never settle for ‘ok’ or ‘good,’” explains Holly. “Together with our team and partners, we’re always going to go the extra mile to try and find new and better ways of creating experiences for clients.”
When I ask Holly and David what makes their brand different from others on the market, the phrase ‘curious control freaks’ comes up. “This isn’t us necessarily,” clarifies David. “But more the philosophy of the brand and the business culture. We deliver creativity but with control.
“So many travellers are looking for the newest, most interesting and amazing experiences. Curiosity is what drives so many of us to discover things we never knew.
“But when people with high standards go on holiday, they want the ‘i’s’ dotted and the ‘t’s’ crossed in such a diligent way, that there’s a big element of control around every trip, too.
“Everything has to be completely on point, especially if you’re operating at the top of the market where we are,” he explains.
It’s this fiesty combination of curiosity and dedication that has propelled them to success.
It’s also why the couple have forged some impressive connections, with their little black book of contacts now including famous figures and royalty. “A highlight for us was meeting King Charles and Queen Camilla at the opening of a Dream Escape client favourite, The Fife Arms in the Highlands of Scotland,” says Holly.
The Balmoral, Edinburgh.While there are many hotels, properties and partnerships that make a Dream Escape holiday so utterly special, here, Holly and David share their fondest memories of three of their favourite places to stay and the people who supported them from the beginning…
The timeless Balmoral Hotel in the heart of Edinburgh, Scotland
Considered one of the city's most revered hotels, this place has been a constant in David and Holly’s lives even before they started the business.
“I’ve known the hotel since I was young,” says Holly. “My grandparents lived in Scotland and I went to university in Edinburgh. The Balmoral Hotel has always had this presence and is known as the most iconic and luxurious place to stay in the city. I remember attending black tie balls there when I was at university!”
“We also stayed before we started Dream Escape, and it’s now the place that we book so many people into,” says David. “It’s great for families and groups of people and is right at the top end of luxury.”
The Balmoral, Edinburgh.But what elevates the hotel even further is the fantastic team of people waiting behind its grand doors. “We’ll never forget being invited by the General Manager at the time, Franck Arnold, to a dinner party at his private apartment at the top of the hotel,” says Holly.
“He brought in people who had supported the Balmoral that year to watch the Edinburgh Festival fireworks from amongst the grand turrets,” says David.
“It was an intimate gathering of people and he put in all the effort himself – cooking dinner rather than just ordering room service. That was a cultural thing that aligned very well with how we like to do things,” he says.
There are so many other caring, hardworking characters working behind the scenes, with a few particular names on Holly and David’s lips. “David Musk, their Head Concierge, has been invaluable. He’s been with the hotel for most of our journey and has been such a lovely supporter,” says Holly.
“He’s always been very human,” says David. “He deeply cares about our relationship with him and always helps us out. Equally, he bends over backwards for our clients. He’s not an ego; he just makes things happen and works hard.
Sir Rocco Forte, celebrated hotelier and the Chairperson of Rocco Forte Hotels, has been another important partner, particularly during more challenging times.
“The pandemic was difficult for everyone,” says Holly. “But it was particularly brutal for the travel industry when so many of us couldn’t operate as businesses. We were constantly dealing with existing bookings and trying to move them forward.” So, in the quiet, they focused on the invaluable relationships they already had.
“During lockdown, I started a podcast and invited Sir Rocco Forte to feature as a guest,” she explains. (You can listen to the podcast on dreamescape.co.uk/inspiration/podcasts/.) “I wanted to do something creative that was long-term, to ask honest questions and dig deeper. We bonded over the tough times and realised we were all in the same boat, although his daily losses were staggering.
“He is so driven and commercially minded while still being a prominent and important family figure – it’s inspirational. To be able to collaborate with his family in business and to stride forward through the highs and lows is very special to me,” says Holly.
The historic Ashford Castle on the shores of County Mayo, Ireland
Ashford Castle dates back to the 13th century and has evolved from a medieval fortress to the Guinness family home, and then to the grand retreat it is today. Over the years, the castle has hosted royalty, nobility and famous figures, becoming one of Irelands’s most celebrated landmarks.
“The property is incredible, and the General Manager Niall Rochford runs it very well and so calmly,” says David. “When we started sending them lots of business and filling their suites, the relationship just got better and better. There’s also Paula Carroll, their former Sales Director,” says Holly. “We knew of her before we met her; she is an incredible force. “As we started building traction, we needed to go beyond just popping in and seeing properties. We needed to stay and experience it properly, and the team [at Ashford Castle] were so great, asking us when we were coming over.
“The first time we went, we visited with my parents and Paula encouraged us to bring the children, too,” says Holly. “We have fond memories of driving over the bridge and experiencing such a warm welcome from the team. The children loved the dogs and we all tried the tree-top climbing experience – it was very high! We also had a fun private cinema viewing.” These are all experiences that are available as part of a Dream Escape trip.
There have been many happy clients who have visited since. “We booked an insurance company from Switzerland into Ashford Castle,” says David. “We’d previously arranged a crazy castle takeover in Scotland with helicopter flights and supercars. We knew Ashford had to be the place when they requested a similar trip.
“We arranged a classic car tour around Connemara, falconry, whiskey tasting and traditional Irish music. We’d already experienced it, so we could wholeheartedly recommend it all!”
Did you know? Visitors to Ashford Castle have included everyone from kings to presidents, including King George V, writer Oscar Wilde, The Beatles‘ members John Lennon and George Harrison, and US President Ronald Reagan.
The legendary Claridge’s in the centre of Mayfair, London
There’s nothing more iconic than the signature Art Deco flourishes and magical luxury of Claridge’s. However, for Holly and David at the start of their journey, the Maybourne Group (who also own The Berkeley, The Connaught and plenty of other hotels across the globe) was a tougher nut to crack. “It took some time to build our relationship with the Group,” says Holly.
“We were small fry in their minds, primarily operating in Scotland at the start. We surprised the Group by starting to book out their top-end suites.”
Now one of their most cherished and beloved locations, the relationship is stronger than ever. But what makes Claridge’s so timeless and relevant?
“I think the way it stands for tradition but has this ability to reinvent itself makes it such an icon. I also think its impeccable location in Mayfair makes it a firm favourite with our clients,” says Holly.
The hotel has also been on its own journey, including creating a new spa as part of a groundbreaking project. Works began in 2015 and the spa was unveiled in 2022 after experts excavated underground into the Mayfair clay beneath. “We took Holly’s parents to stay,” says David. “Holly’s father is Irish and worked as an engineer – he was obsessed with the Claridge’s television show at the time that showed them digging down three floors to create the new space.
Did you know? Claridge’s stunning spa is a 7,000-squarefoot space designed by interior architect André Fu. Inspired by his visits to traditional Japanese temples and Zen gardens in Kyoto, the three floors are home to a huge heated swimming pool, hair salon, steam room and sauna.
“Originally, they couldn’t find anyone who would do it. Funnily enough, the only person who would take it on was an Irish engineer. He and his team dug everything out by hand – they couldn’t use machines because it would interrupt the hotel and it needed to stay open.
“The team kindly took us down and showed us the inner workings of the whole place, which was incredible. Holly’s father was fascinated!”
There are also many special and timeless traditions that Claridge’s continues to uphold: “There’s the incredible Christmas tree, designed by a different fashion designer each year,” says Holly. “It’s always such a joyous surprise.”
“I especially love the grand hallway,” explains David. “The huge stairway swoops up to the first floor, and both the stairs and hallways were designed to be wide enough so that people in extravagant dresses could easily walk past each other without touching. There’s a true elegance about that – it was built during an era people are still so fond of.”
To delve into Holly and David's captivating 20-year tapestry of travel stories and cherished memories, their anniversary book is launching later this year; for further information please email enquiries@dreamescape.co.uk
Words | Amy Bonifas
