Matt Bowles: My guest today is Dianni Hall. She is a queer Latina solo world traveler and freelancer who has been a full-time digital nomad with no permanent base since 2018. Born and raised in the United States. She started her journey with a solo trip to India and hasn’t stopped since. Dianni is the host of the podcast While She’s Away where she interviews female travelers about their experience and expertise in order to help other women live their best lives exploring the world. She also works fully remotely as a freelancer in content creation and podcast management as she travels the world.

Dianni, welcome to the show.

Dianni Hall: Thank you. You make me sound so cool. Like I love hearing someone read my bio. It makes me sound like such a cool person. So, thank you.

Matt Bowles: I am such a fan of you as a human being and everything that you are up to. So, I am so excited to have you on the podcast today. Let’s just start off though, by setting the scene. Unfortunately, we are not in person today. So, let’s talk about where we are in the fact that we have agreed to make this a virtual wine interview.

We’re kind of starting in the afternoon, so, we’re both going to Rosé all day, a little day drinking on into the evening, sort of happening here. I am actually based today in the Blue Ridge mountains of Asheville, North Carolina on the East Coast of the U.S., and where are you?

Dianni Hall: I am currently in New Jersey. Fairlawn, New Jersey. If anyone happens to know where that is, I’m about a 30-minute ride from New York City. And this is kind of like my home base, where I was born and raised, but where I come back to in between travels to pull back the curtain a little bit. We’re both drinking Rosé like you mentioned, but this is now probably going on my third glass quay in a little bit here. So just so everyone knows, just to preface, set the scene.

Matt Bowles: I have blocked the entire day out as a day drinking with Dianni. And so, we’ve already started our day drinking. We’re now pressing the record about midway through. So, you folks are all going to be able to listen to us finish the bottle of wine that we have already started.

Dianni, I want to start this. All the way back. Just to give folks context on you and your upbringing. And before we even talk about where you grew up, can you talk a little bit about your parent’s story, where they’re from and their experience coming to the U.S.?

Dianni Hall: Yeah, of course. So, I’m Puerto Rican Guatemalan.

My dad is Guatemalan. My mom’s Puerto Rican. On my mom’s side, my grandma was actually the one that was born in Puerto Rico. My mom was born here in the States. And on my dad’s side, my dad was born in Guatemala. He was there until he was about 15 years old, and he actually immigrated to the U.S. around that age and kind of bounced around from Chicago to different places until he ended up in New Jersey, which is where he met my mom.

And we, me and my two brothers, I say we, me and my two younger brothers were born here in New Jersey. And there’s a lot of aspects of that that I think have impacted it. The person that I’ve become today in being a second-generation Latina, just my family in general, we never really traveled much because I think my family or my dad specifically saw travel as more of a result of necessity than as a luxury of like vacations.

And we did take the occasional vacation, but it had a very different sense for him when we were growing up and that’s kind of his journey. And so, I’ve kind of taken that with me as a traveler as well with that in the back of my mind and always kind of recognizing the privilege that comes with what I’m able to do as someone who’s constantly moving around.

This comes from a place of just joy and wanting to live my life the way that I live my life rather than for him it came out of a place of necessity. And he actually hasn’t been back to Guatemala since he came when he was 15, I think part of that is fear of it being different. Then the country that he left, and he’s a little bit nervous about that, but my hope is that at some point we’re able to organize a trip where we go back together because I do have family that is there that I’ve never met that he hasn’t seen in a really long time and be able to experience his home, his country, his youth and kind of see him walk through it again while I’m there with him and be able to reminisce and be a part of that walking down memory lane, I guess.

Matt Bowles: Can you share a little bit about your experience growing up in New Jersey and just give folks a little bit of a sense of the diversity and the immigrant dynamics and then for you coming up there, how you navigated that, Latina identity in an immigrant home and your U.S. identity as you were coming of age?

Dianni Hall: That’s something specifically that has always been a real struggle for me. And I think I have a lot of other Latina friends who really identify with that like internal conflict of being American versus being from wherever they’re from. My like core group of friends that I’ve had since I was in middle school are one of them is from Dominican, one of them is from Colombian, the other one’s Colombian and we’ve just got so much diversity within our friend group. And so, we can all kind of have that conversation and really resonate on what it feels like to be Latina American or Colombian American, or, you know, all of these different things, Puerto Rican American. But for me specifically, I think one of the things that makes my experience a bit more unique compared to my friends is that I wasn’t raised with the Spanish language.

I learned Spanish when I was an adult and I lived in Spain, I learned it more fluently. I of course have like my grandma on my dad’s side doesn’t speak any English. And so, like we would communicate in broken Spanish on my end and her broken English on her end. And it’s really beautiful now as an adult to be able to have conversations with her in a way that I wasn’t when I was younger.

But because I was missing that language, it always felt like that Hispanic part of me, that Latina part of me wasn’t real. And I think we talk about like imposter syndrome when it comes to working in a space that we are new to or like as freelancers or different aspects of that. But I think I can relate that as well to my identity as someone who is Latina.

I always felt like a little bit of an imposter because yes, I am by blood, by birth, by my parents but did I fully identify that being born and raised here in America? Like, did I always know everything there was to know about being Puerto Rican or how to make Puerto Rican dishes or, you know, how to dance salsa and like all these different aspects.

I feel like I didn’t fully have all of those things. And so, as I’ve grown up, I struggled with that when I was younger, because I went to predominantly white schools. And so being in those environments, they would joke about me being Mexican because, of course, all Hispanics are the same we’re all Mexican.

And I would take that with a grain of salt because I didn’t really know any better. But as I grew up and got older and was truly struggling with that, like, kind of identity crisis, and still am, have kind of learned that one, that I’m not alone. There are a lot of other Hispanic Americans, no matter where they’re from, who weren’t taught the language and struggle with that, like, piece of identity.

And taking that opportunity to learn more about those parts of my identity. So, whether it’s going back to those countries by myself or learning more about my grandparents stories of their experiences there, or taking the time to learn traditional dishes. Like around the holidays now, my grandma was teaching me how to make arroz con gandules, which is rice and beans, but there’s a very specific way that Puerto Ricans make it.

And so, we were in the kitchen in her apartment and she’s telling me what to put in it and showing me how to do all these things. And really now cherishing those moments and those memories that like, are the things that I’m going to carry on and be like, these are the things that make me the Puerto Rican and that make me Latina and are part of my identity now that I didn’t realize when I was younger.

Matt Bowles: Can you also talk about your journey embracing your queer identity?

Dianni Hall: That’s a little bit more complicated than embracing my Latina identity, I think, because I was raised super Christian in a very religious household to the point where it’s like we couldn’t read or watch Harry Potter because it was magic and like that’s bad.

So, I will preface and say that I no longer identify as Christian because it just doesn’t resonate with me, and I have members of my family who still very much are so it can be a point of contention at times. But in growing up, I think my process of realizing my own queerness was very much delayed because I went to private schools and was continuously learning the rhetoric of like, being gay is bad.

You’re going to go to hell. Like that was the story. And I’d kind of prolonged it for as long as I could. And then there were moments, I guess, through high school that I was in question and then I felt like that didn’t fully start to come to light until I’d gotten into university because then there was just more diversity.

I wasn’t in kind of this of sheltered home anymore, this sheltered environment, this sheltered like the school system. I was able to meet other people who were queer and like to learn about their experiences, which allowed me to kind of become more okay with my own. And I also like fell in love with a woman, so then it was like, oh shit, I can’t really like, you know, I can’t really hide this anymore, I guess is to say, like, it was easy for me to like, push it off and push it further away until I got to a point where that was actively what was happening.

And then I was like, okay, well. Now, I have to navigate this and I think in that initial, that first relationship with a woman, there was a lot of internalized homophobia that I was working through, that I had just internalized through childhood, knowing how my parents felt and who they were and how much of their identity, their Christianity was, being an adult and navigating being in this relationship.

But the guilt and all of these aspects, it was really challenging. But then I’ve now at 27 have gotten to a place I love who I am and I’m really grateful for those times of that part of my journey, because it’s led me to this place where like, I really had to do a lot of work around. Being okay with who I am and becoming proud, not even just okay of like, yeah, okay, like I’m gay, like that’s eh, but proud of the fact that I am queer and choosing to be really active in queer communities and in queer spaces. And have friends who are also queer and surround myself with that and find so much joy and pride in that.

Matt Bowles: That’s so awesome. Can you also talk about how your interest in world travel initially started to develop when you think back?

Dianni Hall: It’s funny because it comes from that place of sheltered childhood. Like I said, I was raised Christian, and I went to private schools. So, one of those things that private schools offer are mission strips, which I’ve done other interviews and I’m like, let me preface and say that I understand that these are wrong now.

It’s very white savior complex going on that we are sent out to save other people, whatever. I know that it’s morally weird, it’s wrong, but at that time I was 14 when I went on that initial trip and so was very unaware. I was still very much indoctrinated in this Christian faith, and I went on a nine-day missions trip to Honduras. And during that time, we went to like landfills and visited orphanages and all of those things where you’re supposed to be helping the community. We were like helping build schools and different things, but we were also bringing the good word of God, which I say with quotes being with quotation marks.

Please don’t judge me. We were bringing the word of God, whatever. And one of the things that stands out to me is during those nine days, I don’t remember why, but we didn’t have cell phones. I think we were able to call our parents at the beginning, let them know that we got there safe. And then at the end and give them a little bit of a rundown and let them know that we were coming home.

But for the rest of it, like we didn’t have phones. So, there weren’t really any distractions. And I’d found myself just really being immersed in the experience of being there. Yes, the context was a bit iffy, but still meeting local, still getting to see parts of Honduras, still getting to like try local foods and different things I found myself so intrigued by.

And then I was having conversations with friends who were also on the trip. Oh, I miss home. I miss my family. And I was just so happy. I was so in it and so happy to be there. And I think that initial trip had kind of just sparked this curiosity in me of realizing, “Oh, there are other things out there”, because I had never left the country before that.

And so, it was like, “Oh my goodness”, there are other people, there are other things, there are other food, there’s other, of course, languages because they speak Spanish. But it just opened my eyes in a way that hadn’t had happened before then. And that led into me going into university and wanting to potentially join the Peace Corps or study abroad in Italy, or like trying to find different things.

And nothing had really panned out. So, when I graduated university, I was like, well, we’re just going to load up a backpack and fuck off to fuck off somewhere because nothing else has happened. So, I guess I’m just going to have to like to make this happen. But that’s the initial kind of entry way into travel.

Matt Bowles: Well, I know that one of your first major travel experiences was your trip to India. And that was really an impactful part of your now life trajectory. Can you share a little bit about the context of that trip? What led to that trip? And What happened in India?

Dianni Hall: It’s funny because I wasn’t even supposed to go to India. I was supposed to go to South America with my ex-girlfriend and I was saving up money and trying to eventually travel and I was like, okay, I’m not making a ton of money. I have to like pay rent and all these things, but we’re just going to save up as much as we can. And she and I had this talk and I was like, okay, in a few months, once we’ve gotten to this point with our savings, we’ll figure out logistics of like, where we’re going to go, all those things, where we’re going to stay, whatever.

And so, I was saving up money. And I thought she was as well, but because we were, what, 21, 22, broke and just trying to, like, survive at that point, she was like, I haven’t been saving, or I don’t have that much saved. And it presented an opportunity for me to be like, okay, am I going to continue waiting for someone else to go with me and wait for her so we can do this together or am I wanting to do this so badly that I’m willing to just go on my own and do this by myself.

And it did get to that point where I was like, I am happy to just go alone. And then I was on Work Away. And if you’re not familiar, you probably are if you’re a regular listener to this podcast, or you’re in the travel community at all. But for a little explanation, Work Away is just a platform where you can find volunteer opportunities around the world so you can stay for free in exchange for accommodation.

And so, I’d heard about it probably through like Nomadic Matt, like the blog or something. And found this ashram in the south of India that was run by this woman, and it was just all female and you would volunteer doing cooking and cleaning and different aspects and in exchange for a stay in this house and I’d done a call with her. And she was like, yeah, like you can come. And that basically started my trip. And I was like, okay, well, if I’m going to go to India, we also have like other parts of Southeast Asia that are nearby. I could hop over to Thailand, and I can hop over to Vietnam, and I can hop over to Laos, and I can, you know, wherever, Cambodia and there are other places I could go.

So that was kind of the molding of that, that India turned into me traveling for like three, four months. But India itself was so new, unique because, and I think that first place was such a beautiful place for me to start because it was. All of these women, and I was 23, I was quite young, and I’m meeting all of these women who traveled and lived in this way that I didn’t even know was a thing that I could be doing.

Because I was home before then, surrounded by friends and family who’d really never traveled at all, or did on like a two-week vacation basis, so for me to just fuck off to India and meet all these women who like, did this, I was like, “Holy shit, what is thing that people do that I didn’t know that people did?”.

I only thought like nomadic Matt on a blog. I thought he was the only person that did this. And it turns out other people do this. It was pivotal because it was so empowering to see women do it in such different ways. Like from one of the girls was also American and she would travel across the U.S. via motorcycle.

The other girl was Brazilian and had been backpacking for months. Another girl was German and seeing all these women from different places around the world. And they would share their stories with me, and I stayed at that Ashram for three weeks, probably a month before heading off to, I was in Varkala at first and then I headed off to Goa and I volunteered at an animal shelter, dog shelter for another month there, which was another incredible experience.

It was right on the beach. It was a gated area community. And there were like 50 plus dogs that lived there, and it was me and an Australian girl and we were in charge of feeding all of them and taking care of them and people would just bring random dogs off the street or puppies that were like sick. And I remember there was one point where I’ve got like a puppy the size of my palm in my hand and I’m feeding him with a bottle like trying to nurse him back to health and I’m a huge animal person, a huge dog person, so I loved doing stuff like that and I was staying in this little wooden put together hut on the beach.

It was the most eye-opening and life-changing part of that whole trip, but also just my life in general. Like it was the pivotal moment where I was like, “Okay, I can live life differently than I thought I was able to”, and I will be like forever grateful for like that specific part of my life where I decided to do that.

Matt Bowles: Can you talk a little bit about the Ashram and the experience that you had shaving your head while you were there why that happened and what impact you think that entire experience had on you as well?

Dianni Hall: I mean, for anyone who is a traveler and is listening and hearing me reminisce about my first trip, you know what it feels like to be on that.

That very first backpacking trip, that kind of like changes everything for you. But there was another layer with the shaving of my head on that trip and you can’t see me but if you go to my Instagram or go look at pictures, I have very big curly hair. And so, when I left on this trip, I also very had I think it was longer at that time but had very big curly hair. And that was pivotal because at the Ashram, like I said, there was one German girl who had dreadlocks.

And for a little bit more of like setting the scene, there were three levels of the house, and the top kind of had a roof on it, but it was open on the sides. And that’s where all of the girls slept. There were just like mattresses on that top floor laid out next to each other, you each had your mosquito net, maybe like a little desk next to you to put some personal items. But we were just sleeping on mattresses on the floor right next to each other. And she got lice. And that was a concern because we were all sleeping on mattresses next to each other. So, if she got lice, it spreads quite quickly and someone else would end up with it. So, we were all kind of invested in helping her get rid of this, but she had dreadlocks.

So, I remember afternoons like sitting on the balcony and I’m sitting behind her with tweezers like plucking lice out of her dreads trying to get it out. And it wasn’t working because obviously, lice are hard to get out of dreadlocks. And I remember her saying that she really didn’t want to shave her head because she’d worked really hard at getting it to this point and she was really happy with her hair.

I don’t know where this came from. I think it’s something I had kind of thought of randomly here and there. But I looked her in the face, and I was like, look, if you do it, I’ll do it with you. We can do this together. And she was like, okay. And I don’t remember, it was a random day, maybe a day or two after the plucking of the lice.

And I come back and she’s bald. And I still to this day can remember how beautifully radiant she looked with her blue eyes and her big smile. And you could kind of see her whole face and she just looked stunning. And I was like, okay, you’ve done it.

Like I will now do it as well. And I went downstairs, there was a shaman staying with us and he was the only one with clippers and they had one setting, which was like a one, it was as short as possible. And me and some of the girls that evening, like went up into one of the bathrooms and they kind of surrounded me with support and love and watched in the mirror as I shaved off all my hair.

And it was really conflicting because I think my hair has always been just this source of like confidence where people would be like, you are so beautiful, your hair’s so beautiful like we love your curls. And I think part of the reason I had wanted to do it was like a shedding of that portion of my identity, of that image that people had of me.

It allowed me to see like, how did I feel like Dianni without hair? How did I feel as Dianni by herself? And it was a struggle the first two days because you’re shedding some of those identities. And I had met people already in town while I’d been there who’d seen me with hair and now without hair, who were like, “But you had such beautiful hair. Why would you shave it?”.

So, I was navigating other people’s opinions, my own feelings about myself. But I think as days passed, I got to a point where I looked in the mirror and was just like, “Okay, like, that’s you”. This is what we are now, and I’d went on the rest of my travels that way, and it was such a unique experience, because as backpackers or travelers, you know, when you meet people in other countries, it’s an opportunity for them to meet, like, that version of you right then, not the version of you that is from your hometown, or the friends that you have that know all of these past experiences that you’ve had, but you’re meeting this person in this moment as you are. And it allowed me to meet people, like, like, as this other version of Dianni, who I was getting to know and they were also getting to know in this new way, which made it really beautiful.

So, there was that aspect, but the Ashram in general, we were getting up every morning at like 4 a.m. She would come in ringing a bell for us to wake up at 4 a.m. to meditate for an hour and to do yoga for an hour. And there was a shaman there who was kind of teaching us. And the whole focal point of it was just mindfulness.

And so, he was helping us with our meditation practices and also facilitating ayahuasca ceremonies that I did not partake in at that time because I didn’t feel like I was ready. But it was a really beautiful space of beginning this kind of spiritual journey that I think can be intertwined with travel.

So, I was beginning a spiritual journey of my own and then it was facilitated more through my experience at the Ashram and then I think it kind of led into also the rest of my travels on that trip.

Matt Bowles: Well, I definitely want to ask you about your experience in Southeast Asia, where do you go? What you were up to? And I really want to hear about how you experienced Vietnam by motorcycle.

Dianni Hall: Vietnam to this day is one of my favorite places in the entire world because it’s such an incredibly beautiful country.

But basically, after India, I’d headed over to Thailand and I was in Chiang Mai where I’d met someone. A little travel romance occurred, and we ended up traveling. They were supposed to head over to where I would think after Thailand, I was going to go to Laos, and they were going to Vietnam. And after Vietnam, they were heading to Australia to do a working holiday visa and live there.

And so, we spent like a few days in Chiang Mai and then headed up to Pai and spent like two incredibly lovely weeks up there because if you’ve ever been, it’s so stunning and beautiful. And we were just going to food markets and hanging around and just kind of enjoying the chill life there. And. Then they had asked me, we were at a waterfall with like a few other friends.

It was around Christmas time, and they had asked me like, “okay, well, I’m going to Vietnam next”. First, they were going to a monastery, but they’re like, after this monastery, I’m going to Vietnam for two weeks before I head. Do you want to come with me? Like, do you want to do this together? I was like, hell yeah.

I’m like, “fuck yeah, let’s do this”. So, I’d went to volunteer in Pai at another dog shelter for two more weeks where I was there, and then we met up in Ho Chi Minh in Vietnam, and we spent two weeks turned into a month, and we traveled from the south of Vietnam all the way to the north via motorbike. And we didn’t buy one because I met people who’d like to buy a motorbike, traveled the whole thing and then sold it.

I didn’t have enough money to do that. My whole trip was on like 3,000. So that’s, that’s all I had for all of it. And once that ran out, we were done. That’s all I could do. So, there wasn’t enough to do that, but we would rent one in one town and then drive to the next town and then stay for a few nights and then like rent another bike and then take it to the next town.

We’d basically just traveled up the coast, hitting a bunch of different towns that we went to. And I think one of the most memorable moments for me was doing the Hai Giang loop in the north of Vietnam because I’d never seen anything like it. The mountains are absolutely incredible. It’s also terrifying because you’re driving around curves on the edge of these mountains that are so close.

And I’m not the one driving, they were driving. So I’m like on the back, holding on, having no control over this, but like completely trusting them because I couldn’t drive a motorbike and they could, at that point, I did end up doing the Thakhek loop in Laos and that when I drove the motorbike, so I had graduated later on in the trip. I gained some confidence to be able to do it myself, but at that point, they were doing it and I remember it being wintertime. So, it wasn’t the like ideal time to do it. And you think like Vietnam, like warm weather. No, it was absolutely fucking frigid when we did it. And so, we’d bought a bunch of gear beforehand. But I remember having so many layers on and being so cold. But there were still moments where we’d like to pull over and just stop and sit on the side of the road and eat our Bryce wrapped in leaves.

I don’t even remember what it had in it. I’m pretty sure something tofu, but just being able to take in these views was absolutely stunning and driving through these communities and stopping in like seeing kids walking to school and just, I don’t know, so many moments of reflection where you’re seeing like people live their everyday lives in a way that was so completely different from what like everyday life had looked like for me. And this being my first backpacking trip, it was kind of one of my first exposures to what life looked like in different places. So seeing like mothers walking around with like baby strap to their back and them wearing like traditional clothing and all of these different facets and all the little pockets of moments where like I’d gotten to meet locals from staying at a homestay and then it was some holiday and like creating this huge spread of food and being able to sit and talk with them or me and the same person that we’d met and we were traveling together.

We were walking out of a corner store and this group of men were sitting on the sidewalk eating and they just invited us randomly over to sit and eat with them. And so, we’re sitting with them and just chatting and they’re asking questions about us and we’re asking questions about them. And I think all of these moments of like being able to connect in really small ways with locals felt like the biggest parts of my trip, like it’s a really small, like it was just a few hours sitting and, and talking with them, but those are the things that I remember looking back.

Matt Bowles: Well, I know another country that you and I have a shared love for that has had a big part in your travel journey is Spain.

Can you talk about what brought you to Spain and what your experience was like there?

Dianni Hall: There’s so much. Spain will forever and always have the biggest part of my heart in terms of places. And from now, when people ask me like, “Oh, what is one of your favorite countries?”. It’s always Spain. And I think it’s because of just the role it’s played in, like my development as a person.

After that Southeast Asia trip, I went back home. I’m home. And thankfully before I’d gone back home, I was already kind of insatiable in that I need to do more of this. What does that look like? And I’d met someone named Matt, who’s from London and Thailand. And he told me about this English teaching assistant program that Spain does, where you can go and teach English, and they give you a monthly stipend and you can work in a school and all these things.

And I was like, okay, well, that’s an in I’ve worked with kids. I’ve been a nanny. I can totally do this. That’s totally in. And so, I remember being in Thailand, like sitting at a cafe, filling out this application and submitting it, whatever. And then when I get back home, I find out that I got accepted.

And so, I’m starting the whole visa process to be able, to move over to Spain while I’m also working so that I can save up some money and go. And so, after a few months of being home, I, go to Spain. I was placed in this small town, Cartagena. It’s in the south of Spain, a middle of nowhere town. That’s where my school was.

And I lived outside of that in a slightly bigger city called Huelva, which is about an hour south of Sevilla. So just to give you some context of like where I was. And my first eight months in Spain, I was living there. But that initial experience was that I worked in the school and I was completely enamored with the kids that I was working with.

I think every few months I would like to switch grades. And I think my favorite still to this day was one fifth-grade class. And one memory that sticks out to me was like for my birthday, I’d come in and they’d brought me this box of cards that they put together and little goodies. They actually had bought me gifts.

Like they’d bought me a pair of sandals and lip gloss. And I had such a special connection with this specific class. And I remember walking in and I was sobbing because they handed me all these presents and were surrounding me, hugging me and all of these things with this like giant card that they’d all decorated and signed.

And I would spend my lunch periods with them. And I think at that point too, my Spanish wasn’t great. Like I was still learning. And so, there was a little bit of embarrassment in talking to other people. teachers my age, because I feel like I couldn’t fully communicate. So, I would spend my lunches with the kids.

Like I would eat in the teacher’s break room, and I’d head outside, and I would play games with them, and I would practice my Spanish and they would teach me. And it’s some of the fondest memories that I have of being there. And after that, I decided that I wanted to stay in Spain longer. And so, I was trying to figure out how to do that.

And I was like, okay, well, I’ve just worked with kids. I’ve nannied in the States, like I can Au Pair. And I found an Au Pair family in the North of Spain on the Costa Brava. And my friends in the South, he drove me, him and I did a road trip from the South of Spain to the North of Spain to get there. And I stayed with this family who ran a scuba diving school. And so, I was able to get my scuba diving certification for free because they ran the school. But they were the most lovely family, very kind of like hippies, free-spirited and so joyful. And it was an incredible place to stay. And the Costa Brava, if you’ve never been in Spain, is gorgeous. The ocean, the water, it was incredible, but it’s also the most broken I’ve ever been, I think, in my entire life. And there’s something so special about, like, being broke while living in another country, because I think I would just have, like, 20 dollars in my account. Au Pairs make 70 euros a week I think, something like that.

It’s not much. You can’t really do much on that. And so, it was enough for me to like to enjoy little things and be able to have meals out or like pay my phone bill. But that was really the extent of what I was able to do. And from there, I was like, okay, well, let me Au Pair again. Like, let’s just stay longer.

And so, I’d found another family in Madrid and ended up moving to Madrid for a few months. And I was in a Spanish school because you have to take Spanish classes because you’re there as a student technically. So, I was taking Spanish classes and making friends with people from different places in Madrid because I think Madrid is also another melting pot where there’s a lot of people from different parts of the world.

And I think Spain, all of those different kind of experiences in different places came together to just make this really unique time that, uh, It’s the time where I learned Spanish. It’s the time when I learned how to be really scrappy and live in a different country on next to no money and figure out how to make it work.

That’s Spain for me. I love it there so much.

Matt Bowles: It’s a really, really special place. I try to go back as frequently as I can and to go to different parts of Spain because Spain is so distinct and culturally diverse as you go to the different parts of Spain. And so, it’s just such a special country for me, as well.

I want to ask you about one more European country, Dianni. I have been to Greece a couple times, but I have not done a sailing trip through the islands. Can you talk about your experience in Greece?

Dianni Hall: It was actually quite random, I was in Mexico, and I had a friend who’s content creator, reach out and say like, “Hey, I can take a plus one on this sailing trip, med sailors”.

I don’t know if you’ve ever heard of them. They do sail trips around Greece and other places. And she’s like, I can. Take one person for free. Do you want to come? And at that point, my plan was to just travel through Central and South America. But I was like, am I going to pass up on this trip of being able to sail around to different Greek islands for free?

I just have to pay for my flight over there. So, I said yes, and eventually made my way over. And I’d never done a group trip of any sorts, but this was. And it was just so much fun, honestly, and we didn’t have any cell service while we were out there, of course, on the water, which made it really lovely and disconnected.

And I had kind of taken that week off of freelancing and let all my clients know. So, it was a really lovely week of being able to disconnect. But on top of that, I’d connected really well with all of the other people who were on the boat. Like we’d created this just really lovely community. And our sailor, the, Captain, I don’t remember what you call him, but he was from Ireland and we were just all from different places.

And basically, to give it a summary, it looked like a week of him sailing us to a different kind of secluded Cove. And we’d be able to jump off the boat in the morning and swim around until he called us back onto the boat for like breakfast in the morning. And we’d sit around and have breakfast and would sail around to like another area where we could be able to get off and explore said islands and do either hikes or try different restaurants or just kind of exploring our own way. And it was that basically on repeat for several days. And I’m not like a group traveler kind of person, but I think it was like the one unique experience that I would be willing and would be willing to do again in a group context because it allowed me to create community in a way that I, a lot of people talk about group travel doing, but I’ve always just been too stubborn and too much of a solo traveler to like be willing to venture into those group traveling spaces.

But I really did love that. And then after I spent a few days in Athens. With that same friend, just kind of eating our way around and doing those different things. And it was really lovely. It was a lovely week.

Matt Bowles: Well, I also need to ask you about another one of my favorite countries. I was just there a month ago, actually, which is Brazil.

I have been to Brazil four times. Every time I go to Brazil, I just feel like why did I ever leave this amazingly magical country? You know, it’s like people ask me that question all the time. When you tell them you traveled to a whole bunch of countries, like what’s your favorite country in the world?

I’m like, I can’t pick a favorite country. I love them all. They’re like, come on. What is it really? I’m like, “Fine. It’s Brazil”. You know? I mean, I feel like that’s kind of how the conversations go. It’s so special. I want to ask you though, because Sao Paulo, one of my favorite cities, but you have been to Sao Paulo for the Pride celebration.

I have not been there for that. Can you tell folks what that experience was like? Actually, also maybe just starting with your impression of Sao Paulo as a city in general and Brazil, how your experience was in the country and then what was the Pride celebration like?

Dianni Hall: Sao Paulo was one of the first place that I gotten to when I got to Brazil. And I just decided to go there I was in Colombia before then and it was okay, next month is Pride Month, June, where do I want to celebrate pride? And decided on Sao Paulo because apparently, it’s one of the biggest in the world with 3.5 million people or something celebrating it was insane. But before then I got to Sao Paulo a week before Pride started, which I’m really grateful that I did because if you do ever go, one thing I recommend is not just getting there for the actual day, but there are so many events leading up to that actual day that the city’s just holding in all different areas that it’s so worth getting there beforehand.

Cause you can meet people that are very specific to like, LGBTQ is plus is a huge spectrum of people. And so being able to go to like specific events that are happening geared towards you. So, there was like trans parades happening and there were sapphic festivals happening and ones geared towards gay men and all of these different facets of queerness.

And so, when I first got there, one of the most memorable parts was getting to my hostel that I was, had chosen to stay at. I don’t remember if someone else recommended it to me, I still have this. You can’t see cause it’s not a video, but I have the band. Still in my arms because when you stayed there, they gave you a band and you could kind of scan it to get food at the bar and stuff, but this hostel will always be one of my favorites in the entire world It’s called Odakasa and it’s a very much a party hostel. So be prepared for that. But it’s got this amazing energy. Brazilians are amazing. Like, as you’ve said, Brazil is one of your favorite places. I think one of the most special parts are the Brazilians. They are incredible people. They are vibrant people. They’re like loving, warm, want to party people. I was exhausted by the time I left there.

So, getting to the hostel, I walk in and there’s this huge LGBTQ flag on the wall and it just immediately felt like this safe and loving and warm space. And I was hanging out with some of the volunteers that like were workers that were working there who were Brazilian and then also other volunteers and going to different museums or just exploring parts of the city and it was a huge city. I don’t know if it’s somewhere that I would live just because I’m very much like a middle city kind of girl, like a medium sized city. I need something that’s a bit more walkable and Sao Paulo’s huge, but I absolutely loved it, and then I think it’s an incredible place to celebrate Pride because it’s such a queer friendly space, it’s such a queer friendly city, when it is or isn’t Pride, just in general.

So, during that week, I was really lucky because there were a lot of other queries staying at that same hostel. I’d made a nice little group of queer friends, and we would go to the different festivals that were happening and there would be vendors or performances or music and food and all these different things and there was one that was specifically sapphic that we went to sapphic festival which means it was all queer women which was amazing. And the music’s playing and blasting to the streets, and you see everyone just dancing and I have no other way to explain it besides just your joy of being able to celebrate who we are.

We went to like two or three different festivals, and then it led up to the actual day of Pride, which was so massive and so insane and really intense, but I think I would recommend, like, if you’re going with other people, to make sure you do go with other people. It might be a little bit overwhelming alone, and to try and get there early, because going to New York, it’s always kind of like barricaded where the parade starts and where you start, but this is just free for all. But it’s fun because the whole city is kind of vibrating with that energy of celebration.

It was, I think, one of my favorite Prides because you can just, Pride anywhere is probably amazing, but seeing people just fully celebrate themselves and who they are is always my favorite thing to do anywhere I am in the world. So, it was truly amazing.

Matt Bowles: All right. We’re going to pause here and call that the end of part one.

Everything that we have discussed in this episode is going to be in one place in the show notes along with all of the ways to contact, follow Dianni and listen to her podcast. Just go to themaverickshow.com and then go to the show notes for this episode. And be sure to tune in to the next episode to hear the conclusion of my interview with Dianni.

Good night, everybody