Nowadays, probably no one remembers about the time you could ask a concierge of a hotel you are staying at for a valuable advise. What’s the best seafood restaurant in the area? Any coffee places worth checking out? Instead, today an average traveler spends up to 20 hours on the web planning a trip prior to landing in the destination of choice. Porter & Sail is an application inspired by traditional, The Grand Budapest Hotel concierge type, which takes the experience of having a personalized advise to a new, digital level. Beautifully designed and innovation-driven, this service is so much more than another city guide. It is your intelligent, 24/7 helper who provides you with exceptionally relevant information and content. We talked to its founder, Caitlin Zaino, to know more.
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There are quite a lot of digital city guides out there. What makes Porter & Sail different? 
Porter & Sail was born out of my own experiences traveling around the world and constantly asking (or being asked) where to go, and what to do in a city. The great concierge had disappeared from the boutique hotels I’d stay at, and front desk recommendations were lacking. Honestly, I didn't expect someone who worked in a hotel to know the best new bar, a store or a restaurant: I wanted to hear it from a local stylist, a barman, a passionate chef. I truly missed that reliable person on the ground. I wanted Porter & Sail to reflect the best advice imaginable, available where and when I needed it. Once I started to imagine how technology could elevate this entire experience, I was completely obsessed with this idea.
You see, Porter & Sail is much more than just a city guide in digital form. We reimagined city exploration for today’s hotel guests. We’ve come up with this idea of “actionable content”– which is expert tips and images delivered with innovative tools like geo-location, time-sensitive features, push notifications and user intelligence, to ensure that the traveler is virtually taken by the hand and led to each location throughout their stay. You can’t get that from some Louis Vuitton or Lonely Planet guide. And we’ve seen wild success. Guests spend up to 50 minutes in-app per trip, tapping and scrolling addictively through hundreds of screens. We trend above gaming apps!
How is it that the Porter & Sail app reinforces the functions of the hotel concierge? Is there something old-fashioned in it that served as an inspiration?
I’m infatuated with the classic concierge, the Wes Anderson The Grand Budapest Hotel type. For a guest in the upscale hotel of yore, the concierge was the person at your behest, making your stay seamless and unforgettable. He knew everywhere and everyone, and he knew you, too. But nowadays, there are too many places, people, openings and ideas for any one person to stay on top of. And, as a guest, you want that level of service 24/7. That’s where we come in. As the guest uses the app, we’re able to gather information (with their permission) and share it with the hotel. The vision is that when a guest turns up at the hotel, their room is ready, their favorite cocktail is waiting, and their dinner reservations are booked. With Porter & Sail, we make all of that possible again – just like it used to be!
Do you think using the app facilitates the communication between hotels and their guests? Why?
Definitely. Hotels are struggling to remain relevant during the guest’s journey and we’re bringing them back into that ecosystem in a meaningful way. Guest behavior has shifted; they’re not talking to the hotel anymore. Travelers almost never call to make a booking. They’re using Expedia, in which case the hotel receives only minimal information. Plus the average guest spends 20-plus hours online planning a trip, making it less likely to ask the hotel for recommendations when they arrive. Where does the hotel fit in to this equation? A few minutes at both the check-in and checkout.
So, we start by being present where the traveler is – on their phone. Once in the app, guests can contact the front desk, housekeeping or concierge. They can inform the hotel of their arrival time, request restaurant reservations, order room service and view all onsite amenities, restaurants, events and other highlights. Right now we’re testing messaging too, which will directly connect the hotel and guest in-app and on SMS. Everything in the app is linked back to the property where the guest is staying. With Porter & Sail, the hotel is very much the center of the guest experience again.
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Why do you believe being mobile present is important in the 24/7 digital era that we now live in?
If the hotel is struggling to remain relevant, then they need to be where their consumer is: on mobile. Guests bring 2.6 devices with them on a single trip, and they’re using their phones for destination information pre and on arrival. That being said, Porter & Sail is a conduit for a larger experience – one that happens off your phone. A guest may learn about a spot through Porter & Sail and use the app to get there, but once they arrive at that spot, they’re living the experience in real time. We are the conduit, but the wonderment kicks in once they dive into that real authentic moment. 
We came up with this saying, “Tell Jimmy we sent you.” The idea was that our app could get guests to that unique hidden bar, gallery, restaurant in any city, and point you to “Jimmy,” who might be the bartender, waiter, owner, and Jimmy will hook you up with that insider experience that makes your stay unforgettable.
Why did you decide to launch the app in Barcelona? What is so aspirational about this city?
We felt like Barcelona was having a real moment right now. With technology companies, start-ups and innovative influencers descending on the city, you can feel a palpable shift towards the “new.” And hotels are absolutely part of this movement. When we began researching Barcelona, we didn’t expect to find this plethora of young, boutique and lifestyle properties that had come online within the last 12 months. Our partners, including Casa Bonay, Yurbban and Margot House, are new hotel concepts that reflect the creative, innovative scene in the city, and highlight the amazing Catalan talent that is propelling Barcelona forward. We pride ourselves on being ahead-of-the-curve futurists. Riding that wave inspires us, and we could not be more proud to stand alongside the local influencers, writers, photographers, hoteliers, restaurateurs, gallery owners, artists and tastemakers who are making Barcelona the exciting and vibrant city it is today.
What are the criteria for choosing future partners?
We look for hotels that offer their guests authentic, unique and memorable experiences. We are creative professionals, global citizens and boutique travelers seeking the unexpected. Any hotel that caters to that audience is a brilliant fit. Often, these are hotels with forward-thinking owners and staff, who are excited to dive into a new wave of hospitality and to bring creative concepts to their guests. There is immense thoughtfulness put into every detail of these properties, from the glassware, to the in-room welcome gifts, to the music on the rooftop bars. We, too, pay excruciating attention to every detail of our product, and want to partner with hotels that match that obsessiveness around quality.
“Porter & Sail is much more than just a city guide in digital form. We reimagined city exploration for today’s hotel guests.”
The application, the photography and social media pages are all extremely visual. Which part do aesthetics and design play in building both an attractive and functional business?
Travel is beautiful. Wanderlust is aspirational. And we believe that to create obsession with a digital product in this space, you have to provide an extraordinary experience that taps into this emotional, ephemeral response. Our aim is to use imagery and design to invoke desire from the moment you book a hotel until your ride home from the airport. A strong brand is critical in hospitality – especially when working with boutique, lifestyle and luxury properties. Brand is everything for these hotels and the technology that they share with their guests must reflect that ethos, and be as beautiful as it is useful.
Porter & Sail is a premium service created exclusively for the partnering hotels’ guests. Do you think the power of community helps to build loyalty? Won’t this prevent from expanding your audience?
Our recommendations are not by the crowd, nor are they for the crowd. We’d rather mean a lot to that small group of discerning travelers than not much to a large group. But that “small community” of like-minded travelers is absolutely helping to promote loyalty. Our goal is to bring together creative professionals and global citizens from around the world, who seek the authentic when they travel both on and off property.
What are the big plans for Porter & Sail? In which cities would you like to launch your app in the future?
World domination! I love the idea of curating and networking all of the extraordinary hotels in creative capitals all around the world, so that wherever you step off any plane, you know exactly where to head to for a truly extraordinary experience.
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