Your company name is quite distinctive. Where did Winged Boots come from?

We knew exactly what we didn’t want to call the business: we didn’t want to be just another company with “luxury travel” in the title. We were working with a marketing agency and the concept came from the winged sandals of the Greek messenger god and immediately felt different, memorable and slightly intriguing. People often ask where the name comes from – and that’s exactly what we wanted. It sparks curiosity and has become a big part of how we think about the brand’s identity. 

Winged Boots started life as your own “black book” of clients. How did the business come about?

Winged Boots really did begin as a black book of clients. I was working with a number of high-net-worth and ultra-high-net-worth travellers, and over time that client base grew to the point where we realised there was a genuine business to be built around it. What started as a collection of relationships evolved into a luxury travel brand. Fifteen years later, those relationships are still at the heart of everything we do. The business has grown enormously, but fundamentally we’re still focused on looking after a network of clients who trust us with their time, experiences and travel. 

Winged Boots sits within the wider Ocean Holidays Group – how did the bigger picture begin?

The story actually starts more than two decades ago with two sets of brothers. My brother Daniel and I joined forces with George and Harry Hastings to launch what became Ocean Holidays back in 2003. At the time, it was just the four of us and two members of staff. We borrowed £30,000, put some adverts on Teletext and started selling straightforward beach holidays to Spain, the Canaries and city-break destinations. It was very humble beginnings. We certainly didn’t have a grand masterplan for what the business would become. Fast forward 23 years, and that small start-up has evolved into a group of four travel businesses spanning both B2C and B2B travel, employing around 200 people and operating internationally. 

Winged Boots

How is the business structured today?

Today, the group operates across four distinct brands. On the consumer side, we have Ocean Florida, which sends around 50,000 customers a year to Florida, and Winged Boots, our luxury travel and concierge business. Alongside that sit two trade-facing operations. We have our Orlando-based DMC business, which wholesales villa product globally to tour operators and travel companies across the UK, Europe, Canada and increasingly South America. We also have Ocean Trade, which packages holidays for travel agents and works with many of the UK’s major consortia. My day-to-day focus is Winged Boots, which I lead alongside Sales and Operations Director Sam Seals. The wider group benefits from the combined experience and different skill sets of all four founders, with each of us taking responsibility for different parts of the business. 

Has working with family and friends always been straightforward?

Yes, we’ve been fortunate in that way! Of course, like any business, there have been challenges and disagreements along the way, but after more than two decades we’re still working together, still enjoying it and still united behind a shared vision. I think one of the reasons it has worked is that we all bring different strengths to the table. As the business has grown, we’ve naturally developed clear responsibilities and areas of expertise. We may now be running a large business, but the entrepreneurial spirit that got us started with £30,000 and a handful of Teletext adverts is still very much there. What I’m most proud of is not necessarily the size of the business, but the journey itself. We started with an idea, a small team and a lot of determination, and we’ve built something that has stood the test of time in one of the most challenging industries there is.
 

Winged Boots

In 2025, you opened your first retail store in Shenfield. Why did you feel it was the right time to move onto the high street?

It was definitely a leap into the unknown because we’ve always been a highly successful online and relationship-driven business. But we felt there was an opportunity to create a physical home for the brand and to attract a different type of client. Historically, many of our customers have been entrepreneurs, business owners and families in the 35-55 age bracket. We wanted to engage more with clients who value sitting down face-to-face and planning significant travel experiences. The space reflects that ambition. It’s designed more like a lounge than a traditional travel agency, because we wanted somewhere people could relax, have conversations and dream about travel. The response has been fantastic. 

What does the success of the store tell you about luxury travel consumers today?

I think it reinforces something we've believed for a long time: travel is fundamentally human. Luxury travel is a significant purchase. People aren't simply buying a flight and a hotel; they’re investing in experiences, memories and valuable time with family and friends. Despite all the discussion around AI and automation, many clients still want personal interaction. They want to sit with someone they trust, discuss ideas, ask questions and feel confident everything has been thought through. That’s why we’re seeing renewed interest in physical spaces and why we’re already exploring plans for additional locations. 

Winged Boots has always been known for its events programme. Why is that such an important part of the business?

Relationships are everything. We’ve built much of our client acquisition and retention strategy around events. Last year alone, we hosted 11 high-end events attended by more than 450 clients. What started years ago as small lunches and dinners has evolved into golf days, clay-pigeon shooting events, networking evenings and exclusive experiences. Interestingly, it’s become much more than a travel programme too: many of our clients and partners now do business with one another too. We’ve effectively created a community where people build both personal and professional relationships, and that creates value far beyond the holiday itself. 

What defines the typical Winged Boots client?

Many of our clients have grown with us. Some joined us 10 or 15 years ago when their children were young and their travel priorities were very different. Today, those same clients may be travelling as couples, exploring more adventurous destinations or looking for highly experiential itineraries. A large proportion of our client base consists of entrepreneurs, business owners and busy professionals. They lead demanding lives and rely on us to manage their downtime, allowing them to focus on everything else. Ultimately, they value expertise, trust and having somebody who can take care of every detail. 

How are luxury travel trends changing?

We’re seeing a significant shift towards experiential travel. Many clients who previously booked traditional luxury beach holidays are now looking for more complex, multi-centre journeys. They’re asking for Asia, South America, cultural experiences and itineraries that combine multiple destinations. As our clients evolve, we evolve with them. That’s one of the reasons we’re investing in new capabilities and broadening our offering.
 

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Why was becoming a Premier Partner of Black Book important to you?

The timing couldn’t be better for us. Black Book is about helping the luxury travel industry build meaningful relationships, and that’s exactly how Winged Boots was created in the first place. The event and access to the network gives us an opportunity to engage directly with ambitious luxury travel advisors, share what we've learnt over the last 15 years and build new partnerships.

Looking back, what are you most proud of?

Probably the fact that we took what was essentially a black book of clients and transformed it into a successful eight-figure luxury travel business. If somebody had told me 15 years ago that we'd build what Winged Boots has become today, I genuinely wouldn't have believed them. It’s been challenging – travel always is. You’re constantly dealing with events outside your control, from geopolitical issues to weather disruption and global crises. But it’s also one of the most rewarding industries imaginable. What I love most is that despite being competitive, travel remains incredibly collaborative. People support each other, share knowledge and genuinely want to see one another succeed. It’s a brilliant industry to be part of, and we’re excited about what comes next.

Limited places available: apply by 17 July

Be among the first travel advisors to attend Black Book, the new luxury travel event launching this October.

Designed to connect agents with leading luxury brands through pre-matched one-to-one meetings, Black Book offers a unique opportunity to build valuable new partnerships and grow your luxury business.

Places are limited and applications close on 17 July. Apply now to secure your chance to attend.