Future-Proofing Travel with Porter & Sail’s Caitlin Zaino von During

The Co-founder and CEO of Porter & Sail, Caitlin Zaino von During is rewriting the rules of the travel industry. We chat about how to get under the skin of a destination, post-pandemic, eco-friendly adventures and her latest initiative, Hotel Credits.

As high-tech as it is high-touch, Porter & Sail was born out of founder Caitlin Zaino von During's desire to build bespoke, experience-driven travel experiences on a personalised e-commerce platform. Launched in 2015 - at a time when hotels were digitally disconnected to their travellers - Porter & Sail wasn't afraid to disrupt the travel sphere, pushing the hospitality oligarchs to one side and connecting travellers to destinations through hotels. Think of Porter & Sail as a worldly pal whispering insider tips in your ear.

When the pandemic hit, she - like most players in the travel industry - was forced to press pause on the upcoming development plans, which included a booking site so customised it was likened to a dating app. Instead, Caitlin completely pivoted. For many of the hotels to survive, they needed access to near-term cash flow, while travellers needed the reassurance that their favourite hotels would offer the flexibility needed to future-proof their travel plans.

And so, within just a few days, Hotel Credits was born. The platform invites travellers to purchase gift-card-like credits that offer heavily discounted stays and experiences at some of the world's best independent hotels, with most expiry dates stretching into 2021 and beyond. This is the kind of sustainable, supportive spending we can really feel good about.

A firm believer that the future of travel must be socially conscious, Caitlin is helping travellers put their faith back into hotels while encouraging spending in the local economies that need it most. Here, she talks to us about how Porter & Sail are shaking up the travel industry, how to get under the skin of a destination and why, in the post-pandemic travel landscape, travellers will have more power than ever.

Socially conscious spending and shaking up the travel industry with Porter & Sail Founder Caitlin Zaino von During

What was the inspiration behind Porter & Sail?

I had been working at the UN and travelling a ton, staying at some incredible hotels around the world. While the experience was often high-touch, I felt the properties were always a step behind my needs as a digitally connected traveller. For instance, recommendations for where to eat would be in an old binder or handed to me on printed paper from the front desk. This feeling extended beyond the hotel to booking, online travel agencies and the friction in making plans pre-arrival and at the destination. Porter & Sail was created to encourage digital innovation alongside seamless, personalised hotel stays. I wanted to modernise the entire experience, start to finish.

How is Porter & Sail changing the way we travel?

We are daring to take ingrained ideas about hotels and the booking experience and flip it on its head. With Hotel Credits, for example, we reward the guest for flexibility. Travel has always been a space in which to have flexibility in your trip - say, transferable bookings or moveable dates - you have to pay extra for it. We're doing the opposite, giving consumers a discount to have that flexibility.

We're eschewing the accepted ways that hotel communications and travel booking are supposed to happen at an operational level too. We're challenging the rules of the traditional travel industry and writing ones that are consumer-centric and guest-friendly, rather than driven by big commissions.

There is a demand for a new, better way to experience, connect, find and book hotel stays. We're trying to do it in a way that is sustainable and socially conscious too, aware that travel has - and continues to have - a material impact on our current global context, whether that's climate change or the pandemic.

Both professionally and personally, how do you balance being sustainable with encouraging people to travel?

On a professional level, we're supporting hotels that have strong sustainability elements or are connected to empowering local communities, looking at ways that we can extend their initiatives and drive additional capital to their projects. We're partnering with Saira Hospitality too, a non-profit that develops pop-up hospitality schools to provide resources and training to underserved communities. Through our partnership, every consumer has the opportunity to donate to Saira - funds will go directly to supporting the purchase of online training tools, like tablets, to enable distance-learning.

On a personal level, my family and I are reevaluating our travel habits. As the CEO of a travel startup married to a professional at the United Nations, business and leisure travel were a routine part of our lives. But with the pandemic, we are reconsidering the value and necessity of this kind of travel. Our summer destination this year? A local spot, tucked away in the woods, with minimal impact on the environment.

You recently launched Porter & Sail's Hotel Credits initiative. How did that start?

When COVID hit, our business went to zero revenue in a matter of days. Five years of hard work felt obsolete. Our hotels were struggling, calling us panicked about meeting their mortgages and watching their hardworking teams become unemployed.

So, we set out to drive money into hotels, even if they were shuttered. Our idea was to create a gift-card-like platform for consumers to purchase future credits to a specific hotel with a 30-per-cent or more discount. The catch? It's non-refundable, but transferable with super-long expiration dates. In exchange, hotels get cash in the door now, at a time when they need it most. Hotel Credits was built and launched in 48 hours.

A silver lining of the pandemic has been seeing how communities have come together. How can we embrace a communal spirit to make us more conscious travellers?

Hotels have an opportunity to redefine themselves as being connected to communities as much as they are tourists. We've seen this done by early pioneers who support locally entrenched lobbies and cafés. Yet this can be extended throughout the industry; hotels can serve as spaces for the community to gather, be it at the restaurant or bar, or maybe for locals to book a weekend staycation or a spot by a rooftop pool.

We should all be popping into our favourite nearby hotel. It supports the local community while giving you that serotonin hit travelling without having to leave your neighbourhood. Your environmental footprint is small but your impact on local spaces is great, especially when occupancy rates are so depressed. Supporting small can mean supporting hotels, too.

What do you think the travel landscape will look like post-pandemic?

I'm a firm believer that it's fundamentally changed. Pre-pandemic, everyone was an influencer trampling on Unesco sites to snap that picture. There were a million cookie-cutter boutiques dreamed up by big brands. I'm all for the industry growing, but it felt bloated and inauthentic.

My hope is that, post-pandemic, the consumer will hold more power. Consumers are demanding more flexibility, refunds and friendlier cancellation policies. The stream of visitors that hotels were accustomed to has changed, so they need to become more guest-centric.

Lockdown has proven that travel is a must-have for mental health - but it's also shown that travel doesn't have to involve a 24-hour flight. Consumers are realising that you can find great experiences just a drive or train journey away; it is redefining what travel looks like for them and, by extension, the industry.

How can we all support the travel industry post-pandemic?

Travel! Do it in a safe, smart way that meets your level of comfort and follows guidelines. But within that context, figure out what travel is right for you and your family. The industry wants and needs you, and you probably need the break too.

Now, more than ever, travellers really want to get under the skin of a destination. Do you have any tips to help people do this?

Seek out well-researched destination information that is editorially objective. User-generated content and comments can be such an unreliable source. Find the media and journalists that you jive with, and look in those trusted spaces for guidance. Plan like it's 30 years ago; head for magazines and books, eschewing forums and comment boards.

What's your favourite hotel for an off-grid getaway?

Hotel Esencia just north of Tulum. I visited the private and secluded villas a few times when I was living in Mexico City and, to this day, I use the soap it had in the room, just to have a momentary escape.

What about for a US staycation?

Buttermilk Falls Inn & Spa. It's a quick trip from New York City, yet feels a million miles away. The perfect antidote to urban hustle.

And a UK one?

Monkey Island Estate is the stuff of which English countryside dreams are made. The manicured gardens and bridges across the river are the kind of which I've romanticised about since I was a kid.

What about somewhere that's leading the way when it comes to sustainability?

Habitas are where it's at. Its Tulum resort esort is eco-friendly and has a zero-plastic policy. Its affiliate organisation supports art, culture and community infrastructure, and it has worked with our friends, Saira, when training staff for its Namibia property.

We've spotlighted multi-gen travel as the next big trend as people reunite with friends and family post-lockdown. Can you recommend a great place to do this?

It depends on where you live and your needs, but we love the idea of reimagining the summer-camp experience. We're seeking out family-friendly beach resorts, wooded escapes and desert adventures. One favourite, though pretty US-centric, is Getaway Piney Woods just outside of Dallas, Texas. There are 32 handcrafted cabins set among trees - perfect for gathering around campfires and connected holidays. But, equally so, there's no reason to not hop on a short flight to Greece and spend a week (or two) with family and friends on the beach in Crete. At the Minos Beach Art Hotel, book out a private bungalow or suite for six and mix days in the water with walks through traditional Cretan villages.

Where will you be travelling post-lockdown and why?

We're planning our first trip now, and exploring everything from ECO Lifestyle + Lodge in Barbados to Sound View in Greenport, Long Island. We want to continue to isolate as much as possible while also taking in beautiful surroundings and searching for a sense of peace. For me, the water is always the most calming, so we're seeking out beach resorts where we can live in the present, alone on the sand.

What about a destination that you haven't been to but is on your list?

Oh, that's Nayara in Costa Rica. I hadn't heard of it before Hotel Credits, but it's this super-luxe enclave in the tropical rainforest. The treehouse tents with private pools and views of the Arenal Volcano look totally dreamy. It's hands down one of our most popular spots, especially for couples as it's adults-only, and it's easy to see why.

Name some of your favourite hotels in the world.

Faena in Miami, with its over-the-top, whimsical flair but total appreciation for supporting local arts and cultural development. Anything from Bill Bensley, like the Shinta Mani in Siem Reap. Its foundation is also a leader in responsible tourism. And I love Swire's The House Collective, with such dramatic architecture and indulgent experiences.

Any ones to watch or secret recommendations?

We have two hotels in Lisbon, which are really stylish and hip: The Lumiares and The Vintage Hotel & Spa. Both feel super modern and creative, yet crafted and connected too. Exploring Lisbon is such a treat already, but coming back to this super turned-on yet welcoming retreat makes a city holiday feel like a restorative and energising one too.

Finally, what's in your SUITCASE?

Funnily enough, I've been living out of the same suitcase since February, when I left my apartment in Italy for a ski holiday and never returned as the outbreak began to take shape in Europe. So, in my literal suitcase, I'm lugging around thermal underwear in New York's summer heat. In any suitcase though, I pack at least two pairs of vintage pyjamas, complete with pocket squares and slim piping trim.

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