What It Takes to Build a Multi-Market Travel Business in a Volatile Industry

Running a seasonal, multi-market travel business means no two days are the same, and this is exactly what drives More Sailing to stay ahead of the curve, set trends, and respond to everything existing and prospective clients need. Here we explore the journey of building and scaling two companies, leadership insights, and navigating growth within the travel and hospitality sector, with CEO Einar Halldin.

To begin, can you tell us about the mission behind your business? What core values have guided you as you’ve expanded into multiple markets, and what makes your offering stand out in the competitive travel and hospitality sector?

At More Sailing, our mission is simple: to make sailing holidays accessible to everyone, not just those who can afford to charter a whole boat. Most sailing holiday companies require you to book an entire vessel, which is expensive and out of reach for many travellers. We offer individual places on sailing trips across the Mediterranean – in Croatia and Greece – which makes it a much more social, affordable, and flexible experience. Our core values are accessibility, quality, and community. What sets us apart is that we’re not just a yacht charter company; we’re building a community of adventurous travellers who love the sea.

As CEO, what does your role look like on a day-to-day basis while managing and scaling across different regions? Do you have a guiding philosophy or mindset that helps you navigate the complexities of a seasonal and international business?

My focus shifts throughout the year – from route planning and crew coordination in the pre-season, to customer experience and operations during the sailing season, and then marketing and partnerships in the off-season. My guiding philosophy is to stay close to the product: I sail with our guests regularly, because understanding the experience firsthand is the best way to keep improving it. For an international business, clear communication and strong local knowledge are everything.

You’ve built and scaled two companies – can you walk us through your entrepreneurial journey? What key moments or decisions shaped where you are today?

I started my first company out of a passion for sailing combined with a belief that the industry was overcomplicating something that should be wonderfully simple. The decision to focus on individual berths rather than full charters was a pivotal one – it opened up a completely different market. Expanding into Greece was another key milestone, as was launching our UK-focused site to tap into the strong British appetite for Mediterranean sailing holidays. Each step taught me something new about running a travel business across borders.

Leading a business that operates across multiple markets comes with unique challenges – how do you approach leadership within a geographically diverse team? How has your leadership style evolved as the business has grown?

Early on, I was very hands-on in every aspect of the business. As we’ve grown, I’ve had to learn to trust the team and delegate effectively. In a seasonal business, you’re often working with staff across different countries and time zones, so clarity, flexibility, and strong systems are essential. My leadership style has become more focused on culture and communication – making sure everyone understands the vision and has the tools to execute it, even when I’m not in the room.

What lessons have you learned about scaling a niche travel business that other founders might underestimate, particularly in a volatile industry?

The biggest lesson is that seasonality is both a challenge and an opportunity. It forces you to be extremely disciplined about cash flow and planning. Many travel entrepreneurs underestimate how much operational complexity scales with growth – adding a new destination isn’t just a marketing exercise, it requires local partnerships, logistics, and regulatory knowledge. Also: invest in your customer experience relentlessly. In a niche like sailing holidays, word of mouth and repeat bookings are your most powerful growth engine.

Can you tell us more about your team and company culture? How do you maintain alignment, motivation, and consistency across different locations and seasonal staff?

We have a small but passionate core team, supported by skippers and local partners in Croatia and Greece. Maintaining consistency across a geographically spread, seasonal workforce is genuinely hard. We invest a lot in onboarding, clear processes, and making sure everyone – from our office team to our skippers – understands what a great More Sailing experience looks and feels like. Culture for us is built around the love of the sea and a genuine desire to give our guests the adventure of their lives.

The travel and hospitality industry is known for its unpredictability – what are some of the biggest challenges you’ve faced recently, and how are you preparing for future uncertainty?

Like all travel companies, we’ve had to navigate significant disruption in recent years. Weather variability in the Mediterranean, geopolitical shifts, and changing consumer confidence all affect bookings. Our response has been to diversify – both geographically and in terms of the types of trips we offer. We’ve also built more flexibility into our booking terms so guests feel confident booking with us even in uncertain times. Building a loyal community of repeat customers is also a form of resilience: they book early and advocate for us.

On the flip side, what opportunities have emerged from operating in multiple markets? How have these influenced your growth strategy and long-term vision?

Operating across Croatia and Greece has given us incredible insight into what different travellers want from a sailing holiday. British travellers, for example, have a strong appetite for structured, well-organised group sailing trips – which is why we recently launched a dedicated UK site. Scandinavian and German markets have their own preferences. This multi-market perspective shapes everything from our itineraries to our marketing. Long-term, we see significant growth potential across the Mediterranean and beyond.

Scaling internationally often comes with operational and logistical hurdles – what have been some of the toughest challenges, and how did you overcome them?

Finding reliable local partners – marinas, provisioning suppliers, and skippers – in each destination has been one of the most demanding parts of scaling. You can have a perfect product on paper, but if your skipper or marina lets you down, the guest experience suffers. We’ve built this out slowly and carefully, prioritising quality over speed of expansion. Regulatory differences between countries also require careful attention, particularly around maritime regulations and insurance.

Is there anything else you’d like our readers to know – perhaps insights into the realities of building a multi-market travel business, or perspectives that are often overlooked?

I think the biggest misconception about travel entrepreneurship is that it’s glamorous. The reality involves a huge amount of logistics, customer service problem-solving, and operational detail. But when you get it right – when a guest messages you to say it was the best holiday of their life – it makes every challenge worthwhile. For anyone thinking about starting a business in travel or hospitality: focus obsessively on the quality of the experience, and the commercial results will follow.

Looking ahead, what are your plans for the next 12 months and beyond? Are there new markets, services, or innovations you’re particularly excited about?

We’re very excited about our growth in the UK market and continuing to build our presence there. We’re also exploring new Mediterranean destinations and developing more specialised trip formats – from sailing skills courses to wellness-focused voyages. On the technology side, we’re investing in making our booking and customer portal experience even smoother. The goal is to be the go-to platform for multi-destination sailing holidays in Europe.

As an entrepreneur, how are you looking to continue evolving in your own career? What drives you to keep pushing the business forward?

Honestly, the guests. There’s nothing quite like hearing from someone who has just returned from their first sailing trip and is already planning their next one. That feedback loop keeps me motivated. As an entrepreneur, I’m also constantly learning – whether it’s about new markets, new technologies, or new ways to lead a team. I’m excited about the next chapter of More Sailing, and I still feel like we’re only at the beginning of what’s possible.

Travellers can discover upcoming sailing trips and new destinations via our website.

Company: More Sailing Web Address: moresailing.com