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The Travel Diaries
Brian Chesky, Airbnb Co-Founder & CEO
Today’s guest is the co-founder and CEO of Airbnb, Brian Chesky, an interview that has been years in the making, and a real honour.
For billions of us, including myself, Airbnb has completely changed the way we travel. It opened up people’s homes, creating an army of Superhosts in the process, bringing tourists and locals far closer together. It’s no short of lie that Airbnb created a travel revolution.
So you could say today’s episode is both Brian’s and Airbnb’s. For a CEO of his magnitude, it’s clearly hard for him to separate the two. The story of how Airbnb came to be, is not what you’d expect. Brian went to design school, he’s an artist, and came from humble beginnings. In fact, it was cereal boxes that first got Airbnb off the ground - you’ll have to stay tuned to hear Brian explain more about that, as part of the fascinating and surprising twists and turns on the path to Airbnb’s global domination.
Brain’s answers are very philosophical and a goldmine of both travel and business wisdom. As he says himself, he was a host before he was a traveler and many of his answers reflect that mindset. Travel for him is about getting into a locals POV. You won’t get luxury hotels, you’ll get stories of people and experiences.
We also hear at the end how Airbnb are pivoting to drive the next revolution in travel.
I hope you enjoy it.
Destination Recap:
- St Louis, Missouri, USA
- Rhode Island School of Design (RISD), USA
- Los Angeles, California, USA
- San Francisco, California, USA
- Flatbush, Brooklyn, New York, USA
- Tokyo, Japan
- The Walt Disney Family Museum, San Francisco, California, USA
If you want to follow in mine and Brian's footsteps and become a host on airbnb you can go to airbnb.com/host to sign up, and try out airbnb.co.uk/askasuperhost to speak to other UK hosts for advice.
Thank you to today's sponsor, DK Eyewitness. Find their guides on special offer at wordery.com - simply enter the code DKEYEWITNESS at checkout for a 10% discount.
If you’re enjoying the podcast, then it would be wonderful if you could leave a rating or a review on your podcast app - it really makes a big difference because it helps other people to discover the podcast.
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To find out who’s joining me on next week’s episode, come and follow me on Instagram, I’m @hollyrubenstein - I’d love to hear from you.
If you can’t wait until then, there’s always the first five seasons to catch up on, with guests from Sir Michael Palin and Jo Malone, to Sir Ranulph Fiennes and Raymond Blanc.
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Ardal O'Hanlon's Ireland - Bonus Destination Special
41:15||Season 15On today’s bonus Destination Special we’re heading to Ireland, one of my favourite places in the world. Ireland has this special kind of magic. It asks you to slow down, to dig beneath the surface, to chat to the people behind the bar and to take your time - to walk, to wander, to just sit and soak it all up.Joining me is someone who knows the country inside and out - the brilliant comedian and actor, Ardal O’Hanlon. You’ll know Ardal, of course, from TV's Father Ted, where he stole the show as the endlessly lovable Father Dougal - and from the extremely popular BBC series Death in Paradise, where he swapped windswept clifftops for tropical crime-solving in the Caribbean. He’s also an incredible writer, stand-up, and most recently, travel presenter, in The Emerald Isles, his BBC series which explored Ireland’s lesser-known islands, uncovering their culture, music, and wild beauty.In this episode, Ardal shares the places in Ireland that have stayed with him, from childhood summers in Galway and Donegal to his all time favourite destination, a lunar landscape in County Clare, and my favourite part of the episode, his hidden gems, which really bring to life some of the wild islands off the mainland that he visited while making his TV series - a lot to add to your bucket list. We talk about the joy of slowness, the quirks of island life, and his new tour - Not Himself - which he’ll be taking across the UK and Ireland soon.So whether you’re planning a trip to Ireland, dreaming about one, or you’re just here for the stories - settle in and enjoy!Destination Recap:Crockwell, Galway, Co. GalwayConnemara National Park, Co. GalwayMagheragallan Beach, Gweedore, Co. DonegalErrigal Mountain, Co. DonegalThe Burren, Co. Clare Skellig Michael, Co. KerryGreat Blasket, Co. Kerry Tory Island, Co. Donegal Rathlin, Co. Antrim Sligo, Co. SligoSaltee Islands, Co. Wexford Visit Ireland.com for more inspiration planning your trip.Ardal is heading back on tour this autumn with his brand new stand-up show, Not Himself. You can find all the tour dates and ticket info at ardalohandlon.com.Thanks so much for listening today. I’ll be back with a brand new season - Season 15 - in a couple of weeks! In the meantime, come and follow me on Instagram - I’m @hollyrubenstein - and you’ll also find me on TikTok.Jon Sopel
58:16||Season 14Today’s guest is a titan of political journalism - someone whose calm, incisive reporting helped us make sense of the madness during one of the most dramatic chapters in American political history. It’s Jon Sopel, the former BBC North America Editor, who spent eight rollercoaster years covering the United States, through Trump, through Covid, through history being made in real time.He’s interviewed presidents, grilled press secretaries, and yes - even been shouted at by Donald Trump himself.Now, Jon’s back on home turf - though the country he’s returned to isn’t quite the Britain he left behind. In his brilliant new book Strangeland, Jon turns his razor-sharp eye on post-Brexit Britain, peeling back the layers of a nation that feels unfamiliar even to someone who grew up here. It’s part political memoir, part social commentary, and entirely unputdownable.These days, you’ll know Jon as one-third of the brilliant trio behind The News Agents, one of the UK’s most popular news podcasts, which he co-hosts with Emily Maitlis and Lewis Goodall. It’s completely redefined how many people consume the news - and it’s an absolute must-listen if you don’t already.In this episode, we dive into the shifting political landscapes of both the UK and the US and of course, we set off on Jon’s Travel Diaries - from his long stint in Washington D.C. to the sun-drenched Riviera, the energy of Rio, and the beauty of Sydney.Holly’s Destination Recap: Puente Romano Hotel, Marbella, Spain Jon’s Destination Recap:New York City, USA French Riviera, FranceSt Paul de Vence, France La Colombe D’or, St Paul de Vence, France Paris, FranceMusée Marmottan Monet, Paris, FranceJardin du Ranelagh, Paris, France Andia (formerly Restaurant La Gare), Paris, France Afghanistan Rio de Janeiro, Brazil Tokyo, Japan Sydney, Australia Noosa, Queensland, Australia Blackberry Farm, Smoky Mountains, Tennessee, USAMaine, USANantucket, Massachusetts, USAShelter Island, New York, USACosta RicaThe Galapagos RwandaStrangeland: Is This Britain’s New Normal? By Jon Sopel is out in paperback on 29th May (Penguin £10.99).With thanks to my sponsors - UPPAbaby -The new UPPAbaby Minu V3 is available to pre order at all UK stockists nationwide now.Airbnb - Visit Airbnb.com and find out more. Prospective Hosts can learn more about how much they can earn sharing their space through the What’s My Place Worth Tool.Saily - Download the SAILY app and use our code TRAVELDIARIES at checkout to get an exclusive 15% off your first purchase.Thanks so much for listening If you want to be the first find out who is joining me on next week’s episode come and follow me on Instagram, I’m @hollyrubenstein, and you’ll also find me on TikTok.Reeta Chakrabarti
55:18||Season 14This week’s guest is someone who many of us will feel we already know. A calm and trusted presence in our living rooms each evening, she’s one of the most familiar faces in British broadcasting - BBC News presenter, correspondent, and author, Reeta Chakrabarti.Raised in Birmingham, Reeta spent part of her teenage years in Calcutta, India - an experience that would later shape her global perspective both as a journalist and a writer.Her career has taken her all over the world, from covering the war in Ukraine from Lviv, to reporting on the 70th anniversary of Indian and Pakistani independence and most recently, covering the Pope's funeral from Rome. She began her career behind the scenes in radio before making the leap to become a correspondent, and finally landing in the iconic BBC News presenting chair - at the age of 49, no less. Proof that there’s no one path to success and it’s never too late to pivot.Her travel diaries today take us from Italy to Chile, Greece to India and much more.Destination Recap:Holly -Cothelstone Manor, Somerset, EnglandReeta -Calcutta, India Rome, Italy St Peter’s Basilica, Rome, Italy Castel Sant’Angelo, Rome, Italy Lahore, Pakistan Santiago, ChileValparaiso, ChileFranceLviv, UkraineParis, FranceTaj Mahal, Agra, India Amorgos, GreeceBrazilArgentinaFinding Belle by Reeta Chakrabarti, published by HarperFiction, out in hardback, ebook and audio on 8th May*COMPETITION*For your chance to win a 3 night all inclusive stay at LUXME hotel on the Greek island of Kos, head to my Instagram @hollyrubenstein. The winner will be announced on May 20th, T&Cs apply!With thanks to my sponsors today - Citalia - Discover the real Italy with Citalia, the UK’s leading Italian holiday specialists. Let the Italy Experts craft the perfect holiday for you and experience Italy like a Citalian.Airbnb - Visit Airbnb.com and find out more. Prospective Hosts can learn more about how much they can earn sharing their space through the What’s My Place Worth Tool.Saily - Download the SAILY app and use our code TRAVELDIARIES at checkout to get an exclusive 15% off your first purchase Thanks so much for listening today. If you want to be the first find out who is joining me on next week’s episode come and follow me on Instagram I’m @hollyrubenstein, and you’ll also find me on TikTok.Gaby Roslin
38:23||Season 14Today we’re joined by Gaby Roslin. Gaby first burst onto our screens in the early 1990s, co-hosting The Big Breakfast with Chris Evans - a show that would become one of the most iconic breakfast TV programmes in the UK. Since then, she’s carved out an extraordinary career as a presenter and broadcaster, spanning television, radio, and podcasting interviewing everyone from Michael Jackson, to the cast of Friends.Gaby is also a passionate traveller, with a deep-rooted sense of wonder about the world. In this episode, she takes us from the thundering majesty of Victoria Falls in Zimbabwe, a country close to her heart, to the timeless beauty of Rome and Florence in Italy, and the rhythm and soul that captivated her in Havana, Cuba.So let’s dive into the travel diaries of Gaby Roslin.Holly's Destination Recap:Ikos, Andalusia, Spain Gaby's Destination Recap: Zimbabwe Victoria Falls, ZimbabweRome, Italy Florence, Italy Galapagos Islands, EcuadorSan Juan Islands, Washington, USAAlonissos, GreeceHavana, CubaNo 15 Guesthouse Hotels, Bath, England ThailandIndiaHimalayas, NepalThe Nest, The Treehouse Hotel, London, England With thanks to my sponsors today - Citalia - Discover the real Italy with Citalia, the UK’s leading Italian holiday specialists. Let the Italy Experts craft the perfect holiday for you and experience Italy like a Citalian.Airbnb - Visit Airbnb.com and find out more. Prospective Hosts can learn more about how much they can earn sharing their space through the What’s My Place Worth Tool.Saily - Download the SAILY app and use our code TRAVELDIARIES at checkout to get an exclusive 15% off your first purchase Thanks so much for listening today. If you want to be the first find out who is joining me on next week’s episode come and follow me on Instagram I’m @hollyrubenstein, and you’ll also find me on TikTok.Dame Prue Leith
01:06:18||Season 14Today’s guest is quite literally a national treasure. She’s a Dame, a queen of the kitchen, an author, a restaurateur, and of course, the judge who has been serving up wit and wisdom alongside cakes and crumbles on The Great British Bake Off since 2017… it is the one and only Dame Prue Leith.Born and raised in South Africa, Prue moved to London in the swinging Sixties and quickly became a force to be reckoned with in the culinary world. She founded Leith’s - a hugely successful restaurant in Notting Hill that went on to earn a Michelin star - and later opened Leiths School of Food and Wine, which has trained generations of top chefs and food writers.Over the decades, she’s written best-selling cookbooks and novels, been a newspaper columnist, a judge on the Great British Menu, and has sat on countless boards and advisory panels, all while campaigning tirelessly for better food in schools, hospitals, and prisons. Her impact on British food culture is hard to overstate. And now, at 85, she’s showing no signs of slowing down. She’s back on our screens in the new season of her wonderfully warm and personal ITV series, Prue Leith’s Cotswold Kitchen, filmed in her beautiful country home, where she shares family recipes, chats with friends, and brings a bit of sunshine to our screens.If you thought Prue’s adventures were limited to the kitchen, though, you can think again. From the deserts of Turkmenistan and the ancient silk roads of Uzbekistan to beach drives in Western Australia and mountain drives in Bhutan, her travel diaries are as rich and surprising as her legendary glasses collection.So settle in for a deliciously inspiring chat with a woman whose life has been anything but ordinary.Destination Recap:Holly:Elkstones, Chipping Campden, England (Part of Simon Escapes' collection)Prue:TurkmenistanUzbekistanAshgabat, TurkmenistanKruger National Park, South AfricaUmhlanga Rocks, KwaZulu-Natal, South AfricaIpswich, EnglandParis, FranceCape Town, South AfricaPerth, Western AustraliaKalgoorlie, Western AustraliaLucky Bay, Western AustraliaCore by Clare Smyth, London, EnglandCotswolds, EnglandBhutanAmir Temur Mausoleum, Gur-e Amir Complex, UzbekistanSharm El Sheikh, EgyptThe Kimberley, AustraliaPrue Leith’s Cotswold Kitchen continues on ITV1, ITVX, STV and STV Player on Saturday 19th April 2025With thanks to Wexas, Airbnb and Saily for their support of today's episode - Download the SAILY app and use our code TRAVELDIARIES at checkout to get an exclusive 15% off your first purchase Thanks so much for listening today. If you want to be the first find out who is joining me on next week’s episode come and follow me on Instagram I’m @hollyrubenstein, and you’ll also find me on TikTok.The Budget Travel Special with Chelsea Dickenson aka Cheap Holiday Expert
54:57||Season 14Welcome to our first Budget Travel Special! This is one that you, the listeners, have been asking for a lot - and I get it! Travel can feel expensive and overwhelming, but what if I told you that it really doesn’t have to be?That’s why I knew I had to bring on the ultimate budget travel expert - someone who has made it her mission to help people travel smarter, stretch their money further, and still enjoy incredible experiences, Chelsea Dickenson, aka the Cheap Holiday Expert.Chelsea has built a huge following all thanks to her easy-to-follow, no-nonsense travel hacks. You’ve probably seen her viral videos on how to snag the best hotel upgrades, fly for less, or even go on an amazing holiday for under £100. And if you’re a fan of This Morning, you’ll recognise her as their go-to expert for low-cost travel. She’s also the co-host of Passports Please, the travel podcast that helps you hack your holidays. Now, I know budget travel is something so many of you are interested in, and you’ve sent in loads of brilliant questions on Instagram for this one. We’re covering everything, from whether five-star hotels are actually worth it to the best destinations where your money goes furthest, plus Chelsea’s ultimate flight-booking hacks that will save you time and money. So, whether you’re planning your next getaway or just love hearing about the best travel tricks out there, this episode is packed with useful tips and plenty of fun stories too.Destination Recap:Berlin, Germany Krakow, Poland Wroclaw, PolandGdansk, Poland Budapest, HungaryKozmo, Budapest, HungaryVilnius, Lithuania Seville, SpainTurkey Nidum Casual Luxury, Innsbruck, Austria Vietnam Ha Long Bay, VietnamCat Ba Island, VietnamKoh Lanta, ThailandDubaiIcelandChill out hostel, Zagreb, Croatia South KoreaUzbekistan Today's episode was produced by Alexandra Calder.With thanks to Visit Guernsey and Airbnb for their support of today's episode.Thanks so much for listening today. If you want to be the first find out who is joining me on next week’s episode come and follow me on Instagram I’m @hollyrubenstein, and you’ll also find me on TikTok - I’d love to hear from you. And if you can't wait until then, remember there’s the first 13 seasons to catch up on, that's over 145 episodes to keep you busy there.Charlotte Church
01:07:20||Season 14My guest today is a true force of nature. From the moment she burst onto the scene as a child prodigy with that voice, she became one of the most famous classical singers in the world, performing for presidents, popes, and royalty. It is of course, Charlotte Church. Her early career was a whirlwind - global fame, relentless travel, and a life that few could truly understand. We talk about what that was really like behind the scenes, the highs and the inevitable challenges of growing up in the spotlight, and how travel became both an escape and a source of inspiration for her.But Charlotte’s journey didn’t stop there. These days, she’s also the founder of The Dreaming, a magical retreat space in rural Wales dedicated to healing, creativity, and connection. Throughout the year, The Dreaming hosts a range of immersive retreats - some focused on families, others on music and self-discovery, including Charlotte’s own deeply personal Song of the Soul retreat. It even celebrates ancient traditions with gatherings around the folkloric calendar, from the Spring Equinox to Halloween.Charlotte’s travel diaries take us from the neon-lit streets of Tokyo to the wild beauty of Dominica, the savannahs of Kenya, and, of course, the rolling green hills of Wales, her home. Her outlook on life is truly unique - spiritual, alternative, and deeply connected to nature and the world around her. So, this is a conversation you won’t want to miss. Let’s get started - here’s Charlotte. Holly's Destination Recap:Homewood, Bath, EnglandCalcot & Spa, Tetbury, England via PoB hotelsCharlotte's Destination Recap:Brazil Lake Geneva, Switzerland Los Angeles, CaliforniaTokyo, Japan The Dreaming, Elan Valley, Wales KenyaElan Valley, Wales St David’s, Pembrokeshire, WalesLlanidloes, WalesAnglesey, Wales The Gower, WalesMerthyr Mawr, WalesDominica Pittsburgh, USAPeruJapanYellowstone National Park, USACosta RicaYou can find out more about Charlotte's retreats at The Dreaming.co.ukWith thanks to Airbnb for their support of today's episode.Thanks so much for listening today. If you want to be the first find out who is joining me on next week’s episode come and follow me on Instagram I’m @hollyrubenstein, and you’ll also find me on TikTok - I’d love to hear from you. And if you can't wait until then, remember there’s the first 13 seasons to catch up on, that's over 145 episodes to keep you busy there.Nile Rodgers
56:50||Season 14I can’t quite believe we’re here - Season 14! And what a way to kick things off because today’s guest is nothing short of musical royalty. Nile Rodgers is a man whose music has shaped generations. A Rock & Roll Hall of Fame and Songwriters Hall of Fame inductee, he’s the genius behind some of the biggest songs in history, think Le Freak, Good Times, and We Are Family. As the co-founder of CHIC, he pioneered the sound of disco and funk, but his influence didn’t stop there. From producing Let’s Dance for David Bowie to Like a Virgin for Madonna, working with legends like Diana Ross, Duran Duran, and Daft Punk, Nile’s fingerprints are all over some of the most iconic records of all time. And that’s before we even get to Get Lucky, the global smash hit with Daft Punk and Pharrell that introduced his magic to a whole new generation.Beyond his music, Nile’s life is an incredible story of resilience, of reinvention, and creativity. His journey from the streets of New York to the biggest stages in the world is filled with extraordinary moments which he shares with us today. And since we recorded, Nile has had even more reason to celebrate, because at the Grammys, Beyoncé officially made history by winning Country Album of the Year - Nile worked with Beyoncé on the record which we discuss on the episode today, and he’s long been an advocate for breaking boundaries in music, so I can only imagine how much joy that moment brought him. We spoke in December at the stunning Royal Lancaster Hotel in London, in a beautiful suite overlooking the rooftops of the city. If you’re new to the podcast, this interview is not how my voice typically sounds, I was ill and could barely speak unfortunately, but that didn’t get in the way of what I look back on as a magical conversation. Destination Recap:New York city, New York, USASao Paolo, Brazil Power Station Recording Studio, New York, USA Los Angeles, California, USA JapanProvidenciales, Turks and Caicos Iceland Montana, USAKazakhstanNile and CHIC will be touring across the UK and Europe this summer, bringing the good times (literally!) to a stage near you.With thanks to Airbnb for their support of today's episode. Thanks so much for listening today. If you want to be the first find out who is joining me on next week’s episode come and follow me on Instagram I’m @hollyrubenstein, and you’ll also find me on TikTok - I’d love to hear from you. And if you can't wait until then, remember there’s the first 13 seasons to catch up on, that's over 145 episodes to keep you busy there.Lily Allen - British Columbia Destination Special
52:49||Season 14I’m so excited to bring you the third and final holiday special to round off 2024. And once again thank you for tuning in throughout the year—your support has been incredible. On today’s Destination Special we’re joined by a truly extraordinary guest—someone who’s not only a trailblazer in the music industry but also a passionate traveller with a love for extraordinary adventures. She’s a singer, songwriter, actress, and cultural icon whose music has been the soundtrack to so many of our lives. Yes, Lily Allen is here on The Travel Diaries!Lily’s debut album, Alright, Still, launched her to global stardom, and since then, she’s won BRIT Awards, Ivor Novellos, and devoted fans worldwide. But what you might not know is that Lily is also an avid traveller, and her recent trip to British Columbia is one of her most unforgettable yet.British Columbia is Canada’s westernmost province, a land of extraordinary natural beauty where dramatic coastlines meet ancient cedar forests, and snow-capped peaks plunge into pristine fjords. It’s a destination that feels alive with adventure and wonder. Getting there from the UK couldn’t be easier—just hop on a direct flight to Vancouver. Vancouver itself is surrounded by ocean and mountains, making it one of the most picturesque city settings in the world—and certainly one of my favourites.From Vancouver, the possibilities are endless. You can take a floatplane to a remote coastal lodge, drive along the breathtaking Sea-to-Sky Highway, or catch a ferry to Vancouver Island. Whether you're exploring the city’s cultural gems or heading into the wild for close encounters with nature, BC offers something for every kind of traveller.In this episode, Lily takes us along for her unforgettable journey through BC. We’ll hear about her encounters with humpback whales, bears, and orcas. and how the restorative power of its nature left her mind at peace and her heart full - Lily calls it one of the most special experiences of her life, and you’ll soon understand why.Destination Recap: The Loden Hotel, Vancouver Tofino, Vancouver IslandCathedral Grove Forrest, Vancouver IslandHot Springs Cove, Vancouver IslandWolf in the Fog, Vancouver IslandAlert Bay, Cormorant IslandAlert Bay Lodge, Cormorant IslandIf you’d like to find out more about British Columbia, then don’t forget to check out your favourite travel titles, magazines and online guides, and you can also find a lot more information on the tourist board website, www.hellobc.com/Thanks so much for listening today. If you'd like to hear more from the podcast don’t forget to hit subscribe, or if you use Apple Podcasts to press follow so that a new episode lands in your podcast app each week. If you want to be the first find out who is joining me on next week’s episode come and follow me on Instagram I’m @hollyrubenstein, and you’ll also find me on TikTok - I’d love to hear from you.And if you can't want until then remember there’s the first 13 seasons to catch up on, that's over 130 episodes to keep you busy there. Don't forget that all the destinations mentioned by my guests are included in the episode show notes here on your podcast app, and listed on my website, thetraveldiariespodcast.com