The Holafly Podcast

Holafly
  • 5.0 (1)
  • Places & Travel
  • Updated Daily

The Holafly Podcast is a weekly travel show hosted by Harry Jaggard and Travel with Chris, two of YouTube’s biggest travel creators. Each episode features conversations with travelers, creators, and adventurers about destinations, real experiences, and stories from the road. The podcast offers honest, unfiltered discussions, including behind-the-scenes moments, the business side of YouTube, the realities of being a content creator, and what it’s really like to build a life while traveling the world. It invites listeners to join the adventure and see travel from a more authentic perspective.

  1. 3d ago

    How I ended up in a Lebanese PRISON | The Holafly Podcast #18

    In this week's episode of The Holafly Podcast, @harryjaggard and @travelwithchris reunite in Lisbon, Portugal, for one of their wildest conversations yet. What happens when an adventure goes completely wrong? Harry shares the unbelievable story of how a travel challenge in Lebanon turned into an experience he'll never forget, while Chris reveals what was happening behind the scenes. From unexpected situations in the Middle East to exploring some of the world's most misunderstood destinations, they discuss the reality of traveling beyond the usual tourist routes, the kindness of strangers, and the experiences that completely change the way you see the world. They also dive into unforgettable moments from Syria and Somalia, react to some of your craziest travel stories, and put their geography knowledge to the test. 🌍 Have you ever had a travel experience that went completely wrong? Share your wildest story in the comments. We might feature it in an upcoming episode! More from Holafly:Newsletter with exclusive content: https://theholaflypodcast.substack.com More from Holafly: LinkedIn: https://www.linkedin.com/company/holafly/Instagram: https://www.instagram.com/holafly_esimWebsite: https://esim.holafly.com/ LISTEN TO OUR PODCAST ON: 🎧 Spotify: https://open.spotify.com/show/033ErockaMiqATlYCzSjBV?si=bn51HMopTrm6mf8DZGn5dg 🎧 Amazon Music: https://music.amazon.es/podcasts/e78b7798-086e-474b-a662-c63672228390/the-holafly-podcast 🎧 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-holafly-podcast/id6784201832 #HolaflyPodcast #HarryJaggard #TravelWithChris #Lebanon #TravelStories #TravelPodcast #Syria #Somalia #AdventureTravel #Lisbon

  2. Oct 17

    Southeast Asia's most OVERRATED and UNDERRATED places | The Holafly Podcast #17

    Thailand, Cambodia, the Philippines, Malaysia… which Southeast Asian destination is actually worth the hype?In this episode of The Holafly Podcast,  ⁨@harryjaggardtravel⁩  and  ⁨@Travelwithchris⁩  sit down with travel creators Tony and Sara from  ⁨@TheDetourDuo⁩  to talk about what years of full-time travel have taught them about Southeast Asia.From Tony’s unexpected journey from the U.S. Navy to travel filmmaking and the couple’s decision to leave everything behind and build a life around travel, the conversation quickly turns to Thailand, Cambodia, the Philippines, Malaysia and some of the most memorable places they’ve experienced.They discuss why Thailand keeps pulling travelers back, whether its popularity has changed the country, the destinations in Asia they believe deserve more attention, and how their own way of traveling has evolved over the years.They also get into tourism, local hospitality, nightlife, food, travel apps, hidden islands, cultural immersion and why slowing down can completely change the way you experience a country.#Thailand #SoutheastAsia #TravelPodcast #TravelCreators #Backpacking #Cambodia #DigitalNomad #TravelTips #Bangkok #HolaflyMore from Holafly:Newsletter with exclusive content: https://theholaflypodcast.substack.comMore from Holafly:LinkedIn: https://www.linkedin.com/company/holafly/Instagram: https://www.instagram.com/holafly_esimWebsite: https://esim.holafly.com/LISTEN TO OUR PODCAST ON:🎧 Spotify: https://open.spotify.com/show/033ErockaMiqATlYCzSjBV?si=bn51HMopTrm6mf8DZGn5dg🎧 Amazon Music: https://music.amazon.es/podcasts/e78b7798-086e-474b-a662-c63672228390/the-holafly-podcast🎧 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-holafly-podcast/id6784201832INDEX00:00 Trailer03:25 A Tinder Love Story That Turned Into a Travel Adventure06:15 Why They Spent 4 Months in Thailand09:50 Harry's Wild Adventure in the Golden Triangle11:00 Is Thailand the Best Country for First-Time Travelers?14:56 Thailand's Best-Kept Secret Island17:12 The Dark Side of Tourism in Thailand20:20 Thailand Is More Than Parties, Drugs & Nightlife26:13 Southeast Asia Showdown: Most Overrated & Underrated Destinations31:00 The Best Food in Southeast Asia

  3. Oct 10

    From DAKAR Rally to Racing BOATS for Will Smith | The Holafly Podcast #16

    In this week’s episode of The Holafly Podcast, @sarapricemx joins @harryjaggard and @TravelWithChris to talk about a life built around speed, risk and competition.  From starting motocross at just eight years old to racing at the X Games, becoming a professional stunt driver and taking on one of the toughest motorsport events in the world, Sara’s career has taken some unexpected turns. She opens up about the sacrifices behind competing at the highest level, what really happens during the Dakar Rally, dealing with serious injuries, racing against men and women at the same level, and why sometimes chasing a dream means putting everything on the line. We also get into her transition from two wheels to four wheels and now to racing electric boats with Westbrook Racing, owned by Will Smith.  An episode about ambition, resilience, taking risks and constantly learning how to evolve.  More from Holafly: Newsletter with exclusive content: https://theholaflypodcast.substack.com More from Holafly: LinkedIn: https://www.linkedin.com/company/holafly/ Instagram: https://www.instagram.com/holafly_esim Website: https://esim.holafly.com/ LISTEN TO OUR PODCAST ON: 🎧Spotify: https://open.spotify.com/show/033ErockaMiqATlYCzSjBV?si=bn51HMopTrm6mf8DZGn5dg 🎧 Amazon Music: https://music.amazon.es/podcasts/e78b7798-086e-474b-a662-c63672228390/the-holafly-podcast 🎧 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-holafly-podcast/id6784201832 #Holafly #TheHolaflyPodcast #SaraPrice #DakarRally #Dakar #Motorsport #OffRoadRacing #Racing #Motocross #E1Series #ElectricBoatRacing #WillSmith #WomenInMotorsport #ExtremeSports #RallyRacing #TravelPodcast #SaraPrice #DakarRally Chapters 00:00 - Trailer 01:45 - From Motocross to Professional Racing 07:00 - The Injuries That Nearly Broke Her 09:00 - Racing in a Male-Dominated World 12:49 - Inside the Dakar Rally 20:00 - “I Sold Everything to Get There” 30:35 - The Reality of Racing Dakar 32:45 - Racing for Will Smith 36:20 - The Truth About Hollywood Stunts 38:40 - Evolve or Get Left Behind

  4. Oct 3

    The TRUTH About New York City: Prices, Scams & Tourist Traps | The Holafly Pocast #15

    What is New York City really like beyond Times Square and the tourist attractions? 🗽 In this episode of The Holafly Podcast,  ⁨@harryjaggardtravel⁩  and  ⁨@Travelwithchris⁩  sit down with New York creator  ⁨@SarahFunky⁩  to uncover the real side of NYC. From $7,000 apartments and expensive hotels to tourist traps, tipping culture, where to actually stay and the mistakes first-time visitors make, Sarah shares the local knowledge you need before your next trip. She also reveals what happened when she dressed up as a tourist, grabbed a hidden camera and deliberately walked straight into some of New York’s biggest tourist traps. Is New York still the best city in the world? And is it really worth the price? More from Holafly: Newsletter with exclusive content: https://theholaflypodcast.substack.com More from Holafly: LinkedIn: https://www.linkedin.com/company/holafly/ Instagram: https://www.instagram.com/holafly_esim Website: https://esim.holafly.com/ LISTEN TO OUR PODCAST ON: 🎧 Spotify:https://open.spotify.com/show/033ErockaMiqATlYCzSjBV?si=bn51HMopTrm6mf8DZGn5dg 🎧 Amazon Music: https://music.amazon.es/podcasts/e78b7798-086e-474b-a662-c63672228390/the-holafly-podcast 🎧 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-holafly-podcast/id6784201832 #Holafly #HolaflyPodcast #NewYork #NYC #NewYorkCity #Travel #TravelTips #SarahFunky #VisitNewYork #TouristTraps #TravelPodcast #HarryJaggard #travelwithchris Chapters 06:35 Which NYC food spots are overrated? 08:17 What are the biggest NYC tourist scams? 15:33 Why did she quit Disney? 19:52 Where should you stay in New York? 22:23 How Expensive Is New York REALLY? 27:01 When is the Best Time to visit NYC? 32:26 What is living in NYC REALLY like? 33:49 How Much Money Do You Need to Live in NYC? 35:31 Why are there fewer Female Travel creators?

  5. Sep 26

    I Got Drunk With a North Korean Secret Agent | The Holafly Podcast #14

    In this week’s episode of The Holafly Podcast,  ⁨@harryjaggardtravel⁩  and  ⁨@Travelwithchris⁩  sit down face-to-face to talk about the side of travel and content creation that rarely makes it into the final video. Surreal experiences across North Korea, Guatemala, South Sudan and beyond, the conversation quickly goes from creator life to stories that sound almost impossible. They also get into how travelling changes when your life becomes content, the unexpected people you meet on the road, the risks that come with exploring unfamiliar places, and the moments when an ordinary trip suddenly turns into something much bigger. Expect honest creator talk, wild travel stories, quick-fire opinions and a few moments that probably shouldn’t have happened. #Holafly #HolaflyPodcast #HarryJaggard #TravelWithChris #TravelPodcast #TravelStories #NorthKorea #SouthSudan #Guatemala #TravelVlog #AdventureTravel #ContentCreator #YouTubeCreator #WorldTravel #CrazyTravelStories #TravelYouTube Subscribe for more travel stories, honest conversations and crazy experiences from around the world. More from Holafly: Newsletter with exclusive content: https://theholaflypodcast.substack.com More from Holafly: LinkedIn: https://www.linkedin.com/company/holafly/ Instagram: https://www.instagram.com/holafly_esim Website: https://esim.holafly.com/ LISTEN TO OUR PODCAST ON: 🎧 Spotify: https://open.spotify.com/show/033ErockaMiqATlYCzSjBV?si=bn51HMopTrm6mf8DZGn5dg 🎧 Amazon Music: https://music.amazon.es/podcasts/e78b7798-086e-474b-a662-c63672228390/the-holafly-podcast 🎧 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-holafly-podcast/id6784201832 Chapters 00:00 Intro 02:56 Inside North Korea 🇰🇵 09:33 Drinking With a Secret Agent 17:03 2 Truths, 1 Lie 19:49 My Uber Driver Worked for the Cartel 27:03 Questioned About North Korea 31:49 The Most Beautiful Place on Earth 35:25 I Accidentally Started a Tribal War

  6. Sep 19

    Our MOST DANGEROUS Experiences EVER | The Holafly Podcast #13

    For the first time ever, The Holafly Podcast goes in person! 🎙️🔥 @harryjaggard and @travelwithchris sit down together in Lebanon to relive some of the wildest travel stories they’ve ever experienced this time with ALL the details. Some of these moments were caught on camera. Others happened completely off-camera and have never been properly told before. From a boxing match in Nigeria that went completely wrong, to a terrifying night in Panama, chaos in Cameroon, police encounters, unexpected arrests and travel situations that sound straight out of a movie… this episode is packed with stories you have to hear to believe. No filters, no short clips, no missing context — just two full-time travellers finally sitting face-to-face and telling the full stories behind some of their craziest moments around the world. 🎧 Full episode out now on YouTube, Spotify and Apple Podcasts. Subscribe for more travel stories, honest conversations and crazy experiences from around the world. More from Holafly: Newsletter with exclusive content: https://theholaflypodcast.substack.com More from Holafly: LinkedIn: https://www.linkedin.com/company/holafly/ Instagram: https://www.instagram.com/holafly_esim Website: https://esim.holafly.com/ LISTEN TO OUR PODCAST ON: 🎧 Spotify: https://open.spotify.com/show/033ErockaMiqATlYCzSjBV?si=bn51HMopTrm6mf8DZGn5dg 🎧 Amazon Music: https://music.amazon.es/podcasts/e78b7798-086e-474b-a662-c63672228390/the-holafly-podcast 🎧 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-holafly-podcast/id6784201832 Chapters 00:00 Intro 04:13 Boxing match in Nigeria 15:12 Almost die in Panama 23:40 Harry’s Secret Past 28:50 Robbed in Cameroon 39:16 Strip-Searched by Police in Bulgaria 50:50 11 Days in Hospital

  7. Sep 12

    This Actually Will Save You Money | The Holafly Podcast #12

    How do you actually afford to travel full time and which travel “hacks” are actually worth listening to?In this episode of The Holafly Podcast,  @harryjaggardtravel  and  @Travelwithchris  sit down with  @awaytogether  to talk about the money behind a life of travel. From leaving the corporate world and turning content creation into a business to earning money on the road, using points and miles, booking smarter, and deciding when it’s actually worth spending more.They also get into travel gear, accommodation, remote work, cheap vs. expensive destinations, business class, and some of the travel advice that sounds great online… but might be complete nonsense. Whether you’re planning one big trip or trying to build a lifestyle that lets you travel more often, this episode is packed with lessons on getting more value from your money while seeing the world.More from Holafly:Newsletter with exclusive content: https://theholaflypodcast.substack.comMore from Holafly:LinkedIn: https://www.linkedin.com/company/holafly/Instagram: https://www.instagram.com/holafly_esimWebsite: https://esim.holafly.com/LISTEN TO OUR PODCAST ON:🎧 Spotify: https://open.spotify.com/show/033ErockaMiqATlYCzSjBV?si=bn51HMopTrm6mf8DZGn5dg🎧 Amazon Music: https://music.amazon.es/podcasts/e78b7798-086e-474b-a662-c63672228390/the-holafly-podcast🎧 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-holafly-podcast/id678420183200:00 Trailer01:02 The Money Behind Full-Time Travel05:19 When Content Became a Career06:02 How Travel Creators Actually Make Money11:20 Making Money While Traveling16:28 Travel Hacks That Actually Work19:24 The Points & Miles Game22:20 Staying Connected Anywhere23:32 The Two-Card Travel Rule25:47 What’s Actually Worth the Splurge?31:14 Travel Gear Worth Paying For36:31 Cheapest vs. Most Expensive Countries#Holafly #HolaflyPodcast #AwayTogether #TravelHacks #TravelTips #BudgetTravel #TravelMoney #FullTimeTravel #DigitalNomad #TravelCreator #TravelFinance #TravelSmart #ContentCreator #TravelPodcast

  8. Sep 5

    She traveled ALONE to Russia, Azerbaijan and Venezuela | The Holafly Podcast #11

    Some of the countries we’re most afraid to visit can completely change the way we see the world.In this episode of The Holafly Podcast,  ⁨@harryjaggardtravel⁩  and  ⁨@Travelwithchris⁩  sit down with  ⁨@aventuralina⁩  to talk about traveling through some of the world’s most misunderstood destinations including Russia, Venezuela, Azerbaijan, Colombia and more. Alina shares why she continued traveling even when the government told her not to, what it’s really like traveling solo as a woman in these destinations, and how reality often compared with the image she had been given before arriving.They also talk about Harry’s nightmare Azerbaijan road trip, crossing the Russian border, Venezuela’s incredible landscapes, safety versus perceived danger, and why separating a country’s people from its government can completely change the way you travel.Plus: their most overrated and underrated destinations, the best food in the world and the cities they would actually choose to live in.More from Holafly:Newsletter with exclusive content: https://theholaflypodcast.substack.comMore from Holafly:LinkedIn: https://www.linkedin.com/company/holafly/Instagram: https://www.instagram.com/holafly_esimWebsite: https://esim.holafly.com/LISTEN TO OUR PODCAST ON:🎧 Spotify: https://open.spotify.com/show/033ErockaMiqATlYCzSjBV?si=bn51HMopTrm6mf8DZGn5dg🎧 Amazon Music: https://music.amazon.es/podcasts/e78b7798-086e-474b-a662-c63672228390/the-holafly-podcast🎧 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-holafly-podcast/id6784201832Summary:00:00 Trailer01:54 Traveling solo to “crazy” destinations05:22 Azerbaijan completely surprised them10:30 Why fewer women travel these countries12:10 The scary reality of solo travel14:50 Russia: completely different than expected20:38 The truth about traveling Venezuela31:00 Rapid-fire travel hot takes31:42 The most overrated destinations32:41 The world’s most underrated countries35:05 Best city in the world to live36:58 Spain vs Germany: where would she live?#Holafly #HolaflyPodcast #Travel #SoloTravel #Russia #Venezuela #Azerbaijan #TravelStories #FemaleTravel #AdventureTravel #MisunderstoodCountries #TravelPodcast

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About

The Holafly Podcast is a weekly travel show hosted by Harry Jaggard and Travel with Chris, two of YouTube’s biggest travel creators. Each episode features conversations with travelers, creators, and adventurers about destinations, real experiences, and stories from the road. The podcast offers honest, unfiltered discussions, including behind-the-scenes moments, the business side of YouTube, the realities of being a content creator, and what it’s really like to build a life while traveling the world. It invites listeners to join the adventure and see travel from a more authentic perspective.

Information

  • Creator
    Holafly
  • Years Active
    2026
  • Episodes
    19
  • Rating
    Clean
  • Copyright
    © Holafly
  • Show Website
    The Holafly Podcast

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