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

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.

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

And so, within just a few days, Hotel
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

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
, 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

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

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
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

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
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

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
, 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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