Porter & Sail: A smarter way to travel

Established in 2015 in New York, Porter & Sail is a travel app which looks to help make travel a more seamless experience through personalised mobile user experience and smart technology. Working with some of the best boutique hotels around the world, guests can plan and book their stays through Porter & Sail and enjoy room upgrades, late check-outs, keyless room entry, mobile check-in as well as access to a 24-hour concierge. The app is also regularly updated with curated destination guides by the likes of actor Stellan Skarsgard (Stockholm) and musician Moby (LA) and a reservations service which allows you to to making bookings for the top dining spots around town.

Caitlin Zaino von During

We spoke to co-founder and CEO Caitlin Zaino von During to learn a bit more about their service as they start to expand into Asia: 

Tell us a bit about how you came up with Porter & Sail?

I’ve always been totally enamoured with hotels – something about fresh linens every day and always having your bed made. Early in my career, I had the pleasure of staying at some amazing properties around the world, first while working with the UN and later when I pivoted into food and travel media. I’d have these incredible stays at brilliant hotels where every detail was perfect, except their recommendations for how to uncover the destination were dated and disappointing, and how they shared that information with me – paper maps and lists of restaurants on an A4 sheet — was completely incongruent to how I was traveling: on my mobile. It was clear that the exceptional service hotels were bringing to every detail of their properties was totally falling down when it came to digital or the authentic, truly experiential moments I was seeking. Porter & Sail was born out of my attempt to connect hotels that I loved better with their guests both through meaningful recommendations and well-placed, beautifully-crafted technology.

There are so many apps out there, especially travel apps, what does Porter & Sail offer that will make it stand out?

Porter & Sail is for a specific moment in travel: hotel travel. This isn’t a Lonely Planet or Louis Vuitton guide that generally covers a city, regardless of whether you’re in a hostel, AirBnB or big-brand hotel. We have obsessed over creating an entire guest experience that is infatuated with serving each moment of a stay. Our booking environment is personalized and highly curated, based in contextual and proactive discovery; pre-arrival guests are offered exclusive opportunities to upgrade or build their bespoke stay; and in-stay users are given the tools to experience a truly smart hotel, from mobile check-in to keyless room entry, coupled with authentic, real-time destination information. Every aspect of that hotel stay is thoughtfully catered to, with the goal of augmenting guest experience and creating a seamless, instant, and anxiety-free holiday that will anchor memories for a lifetime.

Our content bases itself in editorial integrity and quality that is best-in-class, combined with ahead-of-the-curve UX, stunning UI and innovative technology, like machine-learning. We are as high-tech as we are high-touch, and we reflect the elevated experiences of our hotel partners themselves. This combination, alongside the hotel-focused moment in travel, is truly unique in the space. We are architecting and revolutionizing hotel travel.

Walk us through how your curate hotels to offer as part of your collection? What are the key things you look for and why focus on design-led properties?

We are rigorous in our hotel curation, while also leaning into an instinctual, innate feeling that comes from experiencing a property. We seek out beautiful, forward-thinking design, extraordinary food and beverage, and details that push the meaning of a hotel beyond the lobby walls. We love thoughtful touches and quality products, whether it’s found in the amenities, the wallpaper, the linens, or the art. Being truly of a place – and not just a cookie cutter version of one hotel style recast in multiple destinations – is also a key factor. This isn’t about simply 5-star hotels from big boxed brands, but rather unique and exciting properties that are anchored in a destination.

For us, this is the joy of working with design-led properties. These spaces are often built by innovative owners, architects and designers, who are seeking to serve a creative class meaningfully. Their guests demand smart technology, yet the hotels struggle to understand how to offer on-brand digital experiences that they can stand behind. We saw an opportunity to fill this gap. With Porter & Sail, hotels don’t have to feel the pressure to live as technology companies in order to deliver digital products that speak to their guests.

For you personally, what has been your favourite hotel or travel experiences and what made them so special?

Hotel Esencia just north of Tulum is one of my favorite hotels. There are less than 15 rooms on site and it was the Duchess of Ferrari’s former private residence. When the property was conceived of for guests, they worked closely with the local Mayan community to bring in practices from that tradition. The result is a stunning, luxury space nestled partly within the jungle and partly on the sea. Every detail is well thought of, from how you enter the property to the scents, the spa, and the music in the rooms. The staff to guest ratio means any request is always attended to instantly, and yet there’s a sense of privacy and secludedness that is hard to experience at many Caribbean properties, especially in this region.  

What are the key things you look for when you book somewhere new?

Design, location, size (preferably less than 100 rooms) and anything that stands out, whether its an arts programme or travel-worthy food and drink. Design is absolutely foremost as it tends to reflect the vision of the space and if done well, is followed-up throughout the entire on-property experience.

Tell us a bit more about your ‘insiders’ and the exclusive deals you’ve managed to secure for guests who book through your app.

There’s something wonderful about the feeling of being in good hands that a hotel provides. We’ve applied that idea to our neighbourhood guides and insiders. If you stay at AirBnB, you may go to Yelp for recommendations. But if you stay at a hotel, you want the city’s true experts to point you to the absolutely must-visit places, and to explain why. Your time is too short for a misstep. So our Content team reaches out to those insiders on the ground who really know their stuff. Sometimes it’s well-known names like Moby or Stellan Skarsgard, and other times it’s a Vogue editor or an award-winning chef, who are whispering in a guest’s ear. Our intel is juicily insider. It’s of the ”tell Jimmy we sent you” variety—so you can feel part of the community, the moment you arrive.

The deals are all part of living like a member of the Porter & Sail community. From the moment of finding a hotel and booking, our goal is to have every user feel like they’re already on their holiday being treated like a VIP guest. We want users to have a travel experience with Porter & Sail and feel like they could never have one without us again. From the insider intel, to our exclusive deals, it should feel like a private, global club that you’re now a part of.

How do you think travel has changed over the last few years – with so many review sites and different booking platforms to choose from?

When review sites and booking platforms first came out it was thrilling to have this entire process of travel planning consolidated in one place, with filters and dynamic pricing and that instant gratification of booking. I’m old enough to remember calling hotels for availability…So, these Online Travel Agencies like Booking.com or Expedia, were disruptive and changed entirely how people booked travel.

But decades on, it’s dated. They’ve gone from disrupters to the online oligarchs that are failing to innovate. Reviews and products are mass market, user-generated, and standardized. Sorting through reams of hotels to find the best match is a chore. As technology has evolved and consumers can now access personalized, curated, ‘smart’ recommendations for everything from which shoes to buy to which groceries to order, hotels and these OTAs have not innovated and they’ve failed to keep up. There is an entire generation for whom booking platforms and review sites make no sense. We are standing for that generation.  

How are you looking to approach launching in APAC?

There are the obvious considerations to our product and business, thinking about things like localization, technology expectations, language, market concentration, and how Porter & Sail can and should position ourselves and our brand as a meaningful player in the region. We are outsiders in many ways, but we also bring insider knowledge. So much of our NY team has spent years living in Asia and most of our shareholders are in the region – we are ready and excited.

But putting business implications aside, we’re just thrilled to be launching in these incredible destinations. We like to take each in turn, rather than think about APAC in regional or national terms. And in that sense, there are heaps of brilliant creative capitals we are getting ready to cover, which are brimming with authentic, amazing experiences. Hotels are innovative and forward-thinking, and we’re seeing this move away from the nameless 5-star hotel experience that was prevalent in these destinations for decades. An increase in independent and boutique properties are opening, more firmly rooted in their cities than ever before. Gone are the days of austere spaces because, ultimately, a guest may not remember that chandelier in the lobby, but they’ll always remember the chicken rice from the hawker stall. This is what we’re all about.  

Do you feel like travel needs or experiences differ between places such as Hong Kong, Singapore, London and New York?

Experiences in each destination should differ and our goal is to help our users uncover and celebrate those differences. It is the truly local which makes travel so exciting and we want to be a vehicle to empower our users to access those experiences. If Singapore, Hong Kong, London and New York feel the same as a traveler, then you haven’t gone deep enough. Discovering a city through its people, culture and food is the joy of travel.

That said, I don’t think travel needs differ that much. Ultimately, it comes down to ease and reducing anxiety: how do I get to my hotel, what time is check-out, how can I connect with the hotel, where should I eat and drink, how do I call a car, etc. This is where travelers needs are the same around the world and where digital can provide that seamless, instant and painless experience. If I know I can order a car, find the best spots to eat, chat with my hotel, and open the door to my room all on my mobile, then so many of my needs are taken care of in an instant. For Porter & Sail, we always think about the guest pain point and solving for that.  

Where do you see Porter & Sail going in the next five years?

Revolutionizing travel. Revolutionizing how we find and book hotels. Leading the way for how the next generation experiences a hotel and a destination. We want to define and disrupt the travel space for the future in the same way that Expedia, TripAdvisor and Booking.com had decades ago. We want to stand for the future of hospitality and the future of travel. In five years, I hope we’ve redefined how we travel now.  


In this Story: #travel / #destinations / #hotels & resorts