BOLD

Nadja: Hello everybody and welcome to BOLD, a RoomRaccoon series where we shine a light on very special independent hoteliers who rewrite the rules of hospitality.

I’m your host, Nadja. Today, I’m joined by the dynamic pair behind Cape Town’s Pineapple House and Petit Pineapple House, Lesley and Rupert Sykes. With 15 rooms across two boutique properties, they are proof that great hospitality is all in the details.

After returning from the UK, the Sykes purchased a beautiful 1920s Victorian home in Sea Point, Cape Town with no set plans. What started as a simple property investment turned into a bold, passionate project. And just three months after opening, the world shut down. But instead of hitting pause, they doubled down—blending bold aesthetics, smart tech, and purpose-led partnerships to create one of Cape Town’s most standout stays.

Welcome Lesley and Rupert. So excited to have you on BOLD.

Pineapple House has become one of Cape Town’s standout stays. For someone who hasn’t visited yet, how would you describe the Pineapple House experience?

Lesley: I think because we came into the game with fresh ideas, Rupert and I share a very similar aesthetic. We both enjoy color and boldness. We always loved staying in hotels that didn’t feel like home. So we created a space where every single room is different. We’ve used color as the magnet in each room, and it’s become one of our secret power tools because it allows people to have a different experience when they return.

Often people will see a room on Instagram and call us to request “that pink room” or “the mustard-colored room.” So in many cases, we connect with guests even before they arrive.

The uniqueness also lies in the boutiqueness. Post-COVID, I think people travel looking for connection. When Rupert and I travel, we love meeting people from other parts of the world, and that’s one of the most special parts of having Pineapple House. We love engaging with our guests.

It’s a rewarding business—engaging in connection in a small, intimate space. Sometimes shocking people with the color! But I think that’s our unique selling point.

Nadja: I can totally relate. My boutique hotel only had nine suites, also all individual. Guests would always want to stay in a particular room or definitely not in another. That’s really cool.

You both come from completely different backgrounds, right? Rupert, maybe you want to elaborate. You come from property development, and Lesley from the jewelry world. So you definitely have an eye for aesthetics. How does it feel to jump from such different backgrounds into running two boutique hotels?

Rupert: There’s something about hotels. Everyone has an opportunity to stay in one, whether it’s one star, five star, or boutique. I’ve always had a passion for bold interiors.

From my property development background, I designed and put together a lot of properties. I even studied interior design for a time. My mum always said I had an eye for detail, but it only came out later in life. I worked in a bank for years, in IT, sitting next to a colleague reading Computer Weekly while I was reading a design magazine. That’s when I thought, I’ve missed my calling.

When my contract ended, I started a property development business. When we got back to Cape Town in 2015, we worked closely with an architect to put together 10 Irvington Road. Then the property next door came on the market. It was run down, but nothing I hadn’t tackled before. We got approval to turn it into a five-bedroom home.

One day I said to Lesley, I’m not enjoying property development anymore. Would you be keen on opening a hotel? Her ears pricked up and she said, why not?

Nadja: Amazing story. I want to dig deeper into this because I also rolled into hospitality without prior experience. I thought, how hard can it be?

Rupert: When you start a hotel, believe it or not, it’s much more of an outlay than you think. We had a budget in mind, but like with all these things, we wanted to do it nicely.

Because if you do it cheaply, you’re not going to attract the right type of guest. We had to be clever with our budget, but still make sure the quality was there.

We’ve learned a huge amount over a very short period of time. But now I do think we have a lovely brand — something we can really grow and do something special with. Where the brand takes us, I’m not sure at this stage. But we’ll keep working at it, improving where we can, and making sure that when people come to Cape Town, they enjoy Pineapple House Boutique Hotel.

Nadja: You’re in a competitive space in Sea Point. If you had to give other hoteliers a tip, how do you remain relevant and build an outstanding brand?

Lesley: I think the one thing we learned quickly is that there’s more than enough for everyone. You can never forget that in this business. Taking too much notice of what your neighboring hotel is doing, rather than actually building a relationship with them, is counterproductive.

Each hotel has its own character. And I think by portraying that character honestly, you build trust. We’ve stayed in places where you see the pictures online and when you arrive it’s completely different, and that’s so disappointing. What you portray online has to be what you actually offer your guest. Otherwise they walk in feeling let down, and from there it’s an uphill battle.

So for me, it’s about infusing your personality into your hotel, being authentic, and not worrying too much about what others are doing. Instead, focus on creating positive, collaborative relationships. There’s always going to be a day when your neighbor is full and needs to send a guest your way, or the other way around. You want to be able to lean on each other.

Nadja: Have you formed partnerships with other businesses?

Lesley: For me, in the partnership space, the social impact side has been a very strong necessity for us. Being a family-owned business, and having worked in the NGO space myself, I feel those are some of the most important partnerships we can have.

So we try to weave what we’re doing day-to-day in the hotel with the partnerships we support. For example, all our bath mats are made by a single-mother foundation. It was originally set up in the Joe Slovo Township as the H18 Foundation, and today it’s run by a woman who still has that NGO ethos. They make all our bath mats. We need bath mats anyway, so why not support a local cause?

We also work with Project Playground, a Swedish-run NGO in the Langa Township. If a guest wants a late checkout and we have a room available, we ask for a minimum donation of R400, which goes directly to Project Playground. It’s a really nice way of engaging guests and involving them in the social impact work we care about.

Nadja: That’s great. I know you’re also embracing technology. What’s been the most impactful tech in your day-to-day?

Lesley: I think the way we originally built Pineapple House is as a smart house, looking at energy saving and all the things that are absolutely necessary today.

But in the tech space more broadly, slicker technology has just made our day-to-day job so much easier. Even our move to RoomRaccoon was a huge step forward. It gives us the ability to provide guests with a full solution, a complete package.

For example, they can pre-select things like a bottle of bubbles in their room when they arrive, or book their paragliding in advance. That makes life easier for them, but it also makes our lives easier.

And then, from the functionality side — the reporting, the procedures — you have to have those in place to run well. Having good tech behind you is so important for that.

Rupert: The hotel industry is such a busy industry. You’re doing a lot of things, and guests can be quite demanding. Especially when you’ve got someone coming from a foreign country who knows nothing about South Africa, they want to have their hand held a little.

That’s why at Pineapple House we started a tours and transfers business, called Pineapple House Tours and Transfers. It’s an add-on service, but it makes a huge difference. I always recommend it because it’s so nice to arrive at the airport, be picked up by one of our lovely drivers, and be brought straight to Pineapple House Boutique Hotel.

The great thing is that RoomRaccoon supports this. It lets us offer those add-ons right at the booking stage. So when a guest checks out online, they can choose: “Would you like a bottle of champagne in your room?” or “Would you like to book your transfer?” And when they arrive, everything’s ready.

Nadja: Exactly. Guests arrive after long flights, and they don’t want the stress of finding an Uber with luggage in a new country. You’re considering their journey before they even step inside the hotel, and long after they leave.

You’re also selling apparel, right?

Lesley: Yes, we started that probably about 18 months ago. I actually took my first trip to India with a good friend who knows the country very well. We began slowly, producing a pajama range just to test the waters.

We wanted to see if it was something guests would actually want — would they find it appealing? It needed to be the kind of thing someone could pop in their suitcase as a last-minute gift. But it was also about brand extension.

So we created pajamas with little pineapple details on the collar and a tag that reads Pineapple House Boutique Hotel, Cape Town. It wasn’t just about offering a nice, quality keepsake for guests, but also about keeping Pineapple House top of mind when they’re planning their next trip.

Since then, we’ve slowly introduced other products, and it’s now also become one of our social impact projects. So it’s both a memory for the guest and an additional brand extension.

Nadja: It shows your creativity. People remember not just landmarks, but where they stayed. Hotels are often the heart of the travel experience.

What’s next for Pineapple House?

Lesley: We’re renovating a property in Camps Bay called Lion and Tide. It has beautiful views of Lion’s Head and is just off the Camps Bay strip. It’ll be a 14 to 15-bed boutique hotel with the same look and feel as Pineapple House. We’re doing a slow renovation and plan to launch next season.

Nadja: Wow, congratulations. Now that you’re full-on hoteliers, where do you see independent hospitality going in the future?

Rupert: It’s an interesting space to be in right now because Airbnb is huge. But if you’re good at what you do, if you’re unique and offer a high level of service, there’s always space for you.

People love good service. Not everyone wants to book an Airbnb, then have to head to the supermarket and stock up just to start their holiday. They want to arrive and immediately be on holiday. They want to relax.

That’s where boutique hotels really shine. You arrive, you’re welcomed by a friendly receptionist or manager, shown to your fresh, beautifully prepared room, and maybe there’s even a bottle of wine waiting. It’s that convenience and care that people value.

So I believe if you’re better than your competitor and really deliver, you’ll always thrive in this market.

Nadja: Yes, and often it’s the small details guests remember.

Lesley: For us, it’s the butter at breakfast shaped like a pineapple.

Nadja: In my hotel, I was proud of serving coffee on a silver platter with vintage pieces I found on eBay. Staff wore black dresses and tuxedos—it was a small detail, but people loved it.

So let’s wrap up. From everything that’s happened, what’s the boldest decision you’ve made?

Rupert: We started with nine rooms and lived next door. Then we made the bold decision to move out of our home and turn it into part of the hotel—expanding to 14 rooms. Guests can rent either the nine-bedroom villa, the five-bedroom villa, or 14 individual rooms.

Lesley: At first it was hard to think of our home as a commercial space. But it’s brought so much joy to see guests enjoying the space where we raised our children. We’ve laughed, cried, and lived our lives there. Now it’s a joy to see others creating memories in that home. Expanding from nine to 14 rooms has also been a commercial game changer.

Nadja: That is bold—sharing your home’s soul with others. But clearly very successful. Thank you both so much for your time and for sharing your story. I really enjoyed it and I’m keen to discover more about Pineapple House.