INTRO: This is part two of my interview with Darren Chew, better known simply as Chew. If you did not yet listen to part one, I highly recommend you go back and do that first because it provides some really important context for this episode. If you have already heard part one, then please enjoy the conclusion of my interview with Chew.

Matt Bowles: Well, Chew, you have stayed at some of the most incredible hotels in the world, and I can vouch for that because I have seen your YouTube channel, my friend. I want to ask you first of all to just describe some of these experiences because I am watching these videos of you and your wife taking seaplanes into French Polynesia, into the Maldives, landing on the water, staying in overwater bungalows that surely cost many thousands of dollars per night. And you guys are doing this for free or for incredibly discounted rates. And so, I want to ask you to put people on game as well and share some tactics and some strategies. But first, can you just share a little bit about some of the experiences you have and then we’ll get into how you actually were able to achieve them?

Darren Chew: For sure. My wife is a humongous Hilton fan, and that is because she only stays in the best of the best Hiltons in the world. She thinks that all Hiltons are world of Astoria over water bungalows, because those are the experiences that we’ve had. But we’ve been blessed to be able. A lot of places that people call their bucket list we’ve been able to visit, such as French Polynesia, whether it’s Bora Bora, Tahiti, Mo’orea, whether it’s the Maldives, Seychelles. Every March we go on one of these crazy luxury experiences, and next March, we’re actually going to Mauritius. We’re super excited to go to Mauritius and see that experience. But yeah, it’s just amazing of those. My wife’s favorite experience is the Seychelles. We went to a Waldorf Astoria on a private island called Platte Island that just opened up. We were one of the first people that actually went there and visited. And it’s just amazing there, prior to Waldorf Astoria, being on that island, it was a virgin island. It’s just coconuts that were there. There still are sea turtle nesting places. There’s sea sharks and crabs, and you name it, they have it there. And it’s literally in the middle of the Indian Ocean. It’s crazy.

Matt Bowles: All right, so let’s break down some of the tactics and strategies for people that would love to do a completely over the top, ridiculous luxury experience that they could never afford like this.

Darren Chew: So, one of the best things that has happened with travel, it completely changed my perception, especially with the credit card points and miles game and allowing me to have experiences that I could never, ever dream of. I went to Bora Bora and my whole life I thought I was poor. Like, I was able to just do crazy experience. So, I’ll talk about some of the experiences that we’ve had doing it and how we were able to do it. For example, one of the reasons why my wife loves Hilton is because of the amazing experience that we get and perks that we get by being a Hilton Honors credit card holder. One of my favorite cards is the Hilton Aspire, which has a high annual fee, but the perks that we get from it definitely outweigh the benefit. One of the benefits that they give you is a free night award. So, I pay the annual fee. And just by doing that, I can state anywhere that Hilton has a property.

And I’m not going to use that at the Times Square Hilton Garden Inn. I’m going to go to Bora Bora, an overwater bungalow. Like I’m going to get my annual fees worth out of it. A lot of those things also is that just by having that card, I also get free breakfast, I get room upgrades. I get a lot of things that I do all of these things for my wife that make my wife happy. Get on the good side. So, I’d say the Hilton Honors card. And then also one thing is every time that I have a big purchase, whether that’s paying taxes, whether that’s paying my car insurance, I pay my car insurance every six months, strategically, because I’m going to open a new credit card during that time. If I’m moving, if I have something, I’m opening up a new credit card for the signup bonus. And then from there I’m also referring my wife for it. And I get points for referring my wife. And then my wife will also meet that spend. And now I have a player two that we both can travel affordably with using credit cards.

Matt Bowles: So, if people wanted to start getting into this, and I would love for you to go a little bit deeper as well in terms of thinking about designing a trip like this, because I know there’s a lot of strategy and you and your wife plan really far in advance to be able to get the best of, the best of the premium experiences that you want. So, I’m wondering if you can share a little bit about if somebody wanted to plan an over-the-top trip and say, I want to go to Bora Bora and I want to fly business class and I want to stay in an overwater bungalow and land in a seaplane and do all of the things. What does that planning process look like and what types of hacks or techniques can you share?

Darren Chew: Okay, so there’s two main things that you need to figure out. The first thing is who flies there. And then you want to know who, who has hotels there, because from there that’ll determine your strategy, what it’s going to be like to get there. So, for example, we flew to Seychelles. I’ll tell you how we did the Seychelles trip. We flew to Seychelles. The people that fly to Seychelles, when we looked at it was Emirates, Qatar and I think Air France, we flew with Qatar. So, once we fly Qatar, the first thing in our mind is we got to figure out how we can get points into Qatar’s currency, which is the Avios. So, from there I’m looking at which credit cards can transfer points in the currency that Qatar gets. The good thing is that Qatar uses Avios as their currency. If you are not familiar with points currency, I want to try to dumb this down as much as I can. Avios is their currency that not just Qatar uses, but British Airways uses, Iberia uses.

There’s a bunch of different people in that network of international carriers that use Avios. And if you can transfer your points from the credit card that you have to Avios, you can then use those points to redeem for all of those different airlines. So, the first thing that I want to figure out is which airlines fly there. I found out that Qatar flies there, so I need to get points into Qatar. The good thing is a lot of credit card companies have points that can transfer to Qatar, whether that’s Chase. So, a good beginner card that I’d recommend is the Chase Sapphire Preferred, Capital One also transfers to Qatar. Or you can get Avios currency. One of my favorite cards is going to be the Capital One Venture X, but also even the regular Capital One Venture card is another card that transfers to Qatar. There also are great cards that transfer to it like Citibank cards. Citibank cards can transfer to Qatar.

So, once I figure out who can transfer those points to Qatar, I then need to figure out how many points I need to fly there. So, then you want to do some searches, a good search engine that I use is Seats Aero. It’s a great thing that allows you to search many different airlines and multiple dates to figure out availability. Then you can figure out which card can get you the sign-up bonus to get you the points required to fly over there. And then once you have those, you transfer the points over to that airline and then you redeem the flights and you just pay the taxes and fees on those flights. So that’s one part done with the flights.

The other part you want to figure out is hotels. For me personally, I am not a humongous hotel person. I like to spend my trip outside of a hotel. But there are certain experiences that you can only have at certain hotels and I live for those experiences. So, I’m going to look at which hotels are on those islands and we’ll cater our trip to those islands for those hotels, such as the Seychelles, Platte Island. We found that Hilton has a brand-new hotel and we wanted to figure out how to get there and stay at that hotel. Hilton is one of my favorite hotel companies because there’s no cap on the points that you can use a free night award on if you stay with Hyatt, if you stay with Marriott, if you stay with a lot of these things, their caps, they’ll give you 50,000-point free night awards. You can only spend up to 50,000 points.

Well, when you look at it, the Bora Boras stay or the Maldives day you want to stay at is really 100,000. So now that 50,000 points that you get the free night award you can’t even use at the places that you want to get to. And that’s one thing that I really like about Hilton is that there’s no cap in terms of where you can use those as long as you can find a free knight available. Now this is a great thing that for these days if you have a player too because it’s easier to accrue a good amount of points. So, what I found out was Hilton, I would say every year at least runs promotions where even their basic card or the card with, I think it’s $150 annual fee, which is The Hilton Honors Surpass will give you 130,000 points and a free night award built into it. Those are the times when I get those cards. So, there’s some card, the Hilton Honors regular card, that has no annual fee. It’ll have a promotion where it says 80,000 points and a free night award. I’ll get it. No annual fee. It’ll be a low annual spend, like $1,000 in three months or something. I’ll get it. Then I’ll refer my wife. I get the referral points for referring my wife. My wife gets that card. It’s a $0 annual fee. She gets the 80,000 points free night award. Now we have two nights, and then we have 80,000 points and 80,000 points. It was 160,000 points. That’s three nights at the hotel. And we spent money on our purchases, but we have not spent any money in our annual fees. If, depending on the amount of stays that we want, she can refer me for the Hilton Surpass card. That Hilton Surpass card has $150 annual fee, but it also will give me 130,000 points and a free night award. That’s two more nights. And using those cards, by spending $150 in annual fees, we’re able to get a $15,000 Hilton Platte Island stay that we could never even dream of. And also, with those cars, we get free breakfast. We get so many different perks. We got room upgrades that we couldn’t even dream about.

Matt Bowles: And the free breakfast is a lot more valuable at a spot like that than what most people think about of a regular free breakfast. Can you explain that?

Darren Chew: I know I’m saying free breakfast, so you’re thinking buffet style, but no, these are the best. They have fruit bars; they have sushi bars. At breakfast, they have red velvet croissants. The amazing food and cuisine. It’s more than just experience. And realistically speaking, a lot of these breakfasts, they are really like $100 breakfast. If you were to not have that perk, breakfast would be so expensive. And also, when you’re in these experiences, like we were in Platte Island and Seychelles, you’re on an island, you can’t go anywhere else and get food you need to eat. So just having the breakfast there by itself will at least cover one of those costs to help you save money when you’re traveling as well.

Matt Bowles: And I think the other thing about the super advanced planning is number one, so, you can reverse engineer it exactly as you said, pick out your ideal, most epic experience. Figure out which hotel you need to get points for to do that, figure out which airline you need to get miles to fly on, and then retroactively reverse your strategy so you’re getting the cards and building the points and miles. The other thing, though, is that some of these hotels have blackout dates for the use of points, and some flights as well are going to be more expensive, meaning they require more miles to fly on this date versus another date might be less expensive in terms of the miles required. So how do you plan around that?

Darren Chew: So, I would say within the last year, my wife and I have been way more intentional about the places that we go to. Prior to last year, anywhere we see a cheap flight, we’re going. And that’s why my travel schedule has been so crazy with work, because my wife knows she’s the one with reason. I see a cheap flight to go to wherever, I’m like, oh, there got to be something, dude, let’s go. My wife is like, hi, you going to do that? Because we come back on a Tuesday and we leave on the next Thursday, and you can’t work those two days. Something like, she needs my voice of reason.

So, like you said, because of using points, I had to be way more intentional in terms of planning my trips. Because waiting for availability and getting availability for these resorts and these flights, you have to do them as early as possible. A lot of the calendars open up 330, 350 days in advance. So, a lot of these bucket list travel destinations, it’s not. Not just your bucket list, it’s a lot of people’s bucket list as well, for a reason. So, the further out that you plan, it’ll be better for you to save for that trip, but also allows for the availability. So, what I would say is now at this stage in our life, we’re really intentional about the places that we go to. I still will mix in some, oh, it’s a cheap flight, let’s go. But we go to places for reasons, whether it’s someplace that she wants to go to or I want to go to, or it’s a new hotel that’s there. We do this as far out as possible now.

Matt Bowles: Yeah, I think those are two really good and really different types of strategies, right? Like, a lot of people do that follow the deal, not the destination. Wherever you can get the best deal least expensively, just go there, because surely there’ll be awesome stuff to do there. You’ll see a new country, you’ll have a new experience, and you can learn stuff specially if you’re not really familiar with that particular place. And a lot of people do that. And that’s a really good travel hacking strategy is just look for the best deals where it’s least expensive for you to go from the airport that you’re flying out of and just go there.

But then there’s this other side, which is that if I wanted to architect this super over the top, epic bucket list legendary experience, how would I retroactively do that so that I could have something for free or for a super inexpensively that would normally be totally prohibitive for most people to do. And then you can strategically work backwards and design that particular specific experience in that particular place, which I think is a combination of, of the place and the experience. If I’m hearing that right. It’s like, yeah, we want to see Bora Bora. And also, we want to stay in an overwater bungalow and land in a seaplane and have all of that kind of epic stuff in one. And then you reverse engineer it. Are there any other more advanced or lesser-known hacks or tips or techniques that in doing this for so many years now you can share with folks on top of what we’ve already talked about?

Darren Chew: Even though I’ve been doing it for some years now, the landscape of it is ever changing. There are new people that are added to alliances, there’s new airlines that are joined, there’s new transfer partners, there’s new credit cards that are opening. So, it’s an ever-changing fluid environment. One thing that I realized more recently is one of my favorites, I guess hacks is one of my most valuable points is Alaska Airlines being in New York. I don’t fly Alaska often, but I have found myself trying to get and redeem Alaska points. And the reason why is one thing that Alaska allows you to do is to have, I believe it’s seven-day free layover or stopover in anywhere that you’re going. So, for my birthday as of right now, I have this planned where I really wanted to go to the Uni Salt flats in Bolivia during my birthday. It’s the wet season so you could have that amazing mirror effect. It’s supposed to be one of the most beautiful experiences that you can have.

But I also found that flying with LATAM, who is an Alaska partner, you can actually fly directly into Chile. And I’ve never been to Chile. So as of right now, I booked it to fly direct from New York to Chile. I have eight days in Chile on a stopover and I was looking to see If I can get over to Easter Island. But the flight prices look crazy, so I don’t know if I’m going to do it. But I might just stay in Chile. There’s enough to see in Chile and then from there go Chile to Bolivia. And instead of having a four hour or even 20-hour layover, I have literally eight days and I didn’t pay more for my flight. You just got to find the availability. And Alaska Airlines is a real unique airline because you’re allowed to do those essentially for free. Even if you were to book that separately, the flight from Chile to Bolivia or the direct flight from New York to Bolivia, it’s crazy. So that’s one hack that I think that not enough people talk about. That I think is an amazing feature.

Matt Bowles: It’s a really good one. And there’s different levels of that too. I think sometimes if you are booking a flight and the airline carrier, whatever country it happens to be from, like the national base, they will often invite you as they’re routing you on your layover through that country. Would you like to spend 48 hours or 72 hours in this country on the way? Because you’re welcome to do that, right? I feel like Iceland might have been the one that started it, Icelandic era. And they were like, all these people are going on their route from the US over to mainland Europe and they’re like, do you want to spend like 48 hours, 72 hours in Iceland? Because you’re welcome to do that, get no extra charge and no visa.

And then I just start finding that on all of these other carriers. Last year I was flying from D.C. to Bangkok and I just looked up what’s the cheapest flight from D.C. to Bangkok. And it happened to be on Saudia Airlines, which is the national carrier from Saudi Arabia. And I go on their website because that’s the cheapest way to book it. And they’re like, want to spend 48 hours in Riyadh on your way? Because you got to transfer through here anyways, no extra charge. I’m like, sure. So, you can kind of do that stuff. Or even the really quick hacks are like the stuff that you did in Kenya, which is that you just got 20 hours and you go out and you see the city.

Or even props to the airport in Vienna, Austria, which I think does this better than any other airport I have seen, is they facilitate an experience where if you have a layover of at least like four, four hours. You can lock your luggage that you’re carrying with you in a locker, jump on an express train that shoots you from the airport right into the old city of Vienna. Walk around, get a coffee, hang out for a little bit and then get back on and it shoots you back to the airport. You grab your bag and you go to your gate, right? So, I love the layover experience and the longer you can do it, if you can spend three days, four days, eight days in Chile, that’s going to be amazing. I think that’s a really, really good hack and a great way to see more places.

Darren Chew: For sure. And when you say that there’s so many airlines that offer that. Copa Airlines in Panama, you have Iceland Air in Iceland. We did a Turkish stopover with Turkish Airlines. Qatar Airlines did that we were in Doha two different times where we had that stopover in Qatar. They actually will facilitate and give you the five-star hotel for like $30 a night or something, depending on the stay that you’re doing it. There’s some that will give you free stays. We did it in Singapore as well. And a lot of them will even give you accommodations and transportation and tours throughout the city as well. So, layovers to me get bad reps, but I love me a good layover.

Matt Bowles: Hundred percent. Yeah. And if you can structure it for to spend as much time there as possible, I’m super excited you’re going to Chile. I spent about a month in Santiago. I was based there and it’s just a spectacular city. You’re right near Valparaiso on the coast. You can just do an hour out there, spend the day there. It’s one of my favorite cities as well. But the salt flats in Bolivia. I will say this as much as I talk about how much I love Brazil and I love Chile and I love Colombia, like all these countries. If somebody says to me, I have one week to spend in South America, anywhere on the continent. And I’ve been to Machu Picchu, I’ve been to all these epic places. I know you have too. But if somebody says to me, I have one week to spend anywhere in South America, I’ve never been anywhere on the continent. Where should I go? I’m going to tell them to go to Bolivia, man.

I spent eight nights in Bolivia and I’ve been a lot of, I mean, props to the Galapagos Islands. Like, I’ve been to a lot of epic places in South America. Bolivia, man, it was just something so special and so different and so unique. Like, I went with a group of about eight people and we were in, we were based in Lima, Peru, for the month. And we just were like, yo, let’s just go to Bolivia for a week. We go to Bolivia for eight nights and everybody’s mind was just blown. And these are very experienced travelers I was with. I mean, mine’s just blown every day. Like, we’ve just never seen anything like this. It just feels like you’re on a different planet every day. When you’re in the salt flats and then even when you’re in La Paz, the capital city, people get around in La Paz by cable cars. That’s like the regular form of working-class transportation. I mean, it’s built into the. I mean, it’s just totally different, totally over the top, totally spectacular. So, I’m really excited that you’re going to Bolivia and definitely want to hear about that. I’m excited to see your video because if you’re able to fly your drone and get footage that way as well, man, I know you do, that’s going to be really special.

Darren Chew: I’m excited. That’s why I chose that place for my birthday. Let’s see if that goes through. But that’s the plan. I have flights booked already for us.

Matt Bowles: I love it, brother. Well, Chew, I want to ask you now just for some reflections and tips based on all of the travel that you’ve done so far. I know we’re both going to go to the Black Travel Summit. You’re one of the speakers there. And I know a lot of the content that you do is for black travelers in particular. And I’m wondering if you can share a little bit, just reflecting on your travels, about how have you experienced this, the dynamics of anti-blackness around the world as a traveler. And also, when we say that anti blackness, there’s a lot of intersectional dynamics that go along with that in terms of are you speaking with an American accent, are you speaking with an African accent, and other types of class dynamics and things of this nature. So, I’m curious, at this point in your travel journey, what are some of your overall experiences, but then also reflections and analysis of that.

Darren Chew: By traveling, I realize how different people think about my blackness. I think one hot topic content that goes viral is people saying, going to this place as a black person, I have never done that. I see a lot of people saying that that’s the first thing that they do. First thing is I want to experience a place for myself before I form an opinion on it. Not saying that racism is not a thing that exist. As we all know, racism does exist and there are different layers between that. But I travel with the intention of having experience. And if something racist happens to me, to figure out why that is and how it could have happened the way that it did. But also, I have benefited for a lot of places that I’ve go to because I am American. I have American passport.

I’ve gone to places in Europe and even in Africa where they treat me differently until I open up my mouth and they, oh, this is an American. Like, I am above anybody else because of my citizenship, having an American accent, and it is, I guess, eye opening. We were just recently in Uganda, and when I was in Uganda, people were treating me a certain kind of way because they thought I was Ugandan. And then when I started talking to them, everybody wants to be my friend and everybody wants to be nice to me, which I’m grateful for, that the people want to be nice to me, but it shouldn’t be because I am American. So, I definitely benefit from being an American.

Matt Bowles: Well, I also want to ask you about how all of the travel that you have done together as a couple with your wife has impacted your relationship with her.

Darren Chew: So, this is really interesting because I never traveled as a kid growing up outside of Jamaica, and my family, we used to go on one big trip every year to Florida. And my wife’s upbringing was different than mine, where she went on a lot of family trips. She stayed in nice places and she went to beaches and she relaxed. And her idea of a vacation was different than when she travels with me. And the best thing that I would say about my relationship with my wife is that we are both compromising in each other. I would say that travel has strengthened our relationship because it’s something that we both are passionate about and we learn so much about each other that it’s relationships that we have built with each other. I know a lot of people say that you don’t really know somebody until you travel with them. And I wouldn’t want to travel with anybody but my wife.

Matt Bowles: I recommend that to people all the time. When you get into a relationship with someone, go on a trip with them as early in the relationship as possible. Because when you interact with people on a trip, when you’re traveling together in a place that you’re both not familiar with, you will learn so much about that person. So, when you think back about all the travel that you have done now, starting with going to stay with your teammates in Europe and all of the things that you’ve done up until now, how do you think that all of that travel has impacted you as a person?

Darren Chew: My handle on everything is ChewsToExplore. It has kept me curious. It has helped me explore not just the world, but also different things in my life and avenues that I never considered seemingly possible because of travel. So, I would say definitely opened my mind and kept me curious, kept me adventurous, kept me young.

Matt Bowles: Well, the other thing that you and I have in common is that we are both on team Carry on and we do not check luggage when we travel. And I know your wife is also on team Carry on, which I love. There is a quote on one of your blog posts. It says we’ve never checked a bag. For us, minimalist packing has become more than a strategy. It’s a lifestyle choice for travel that’s worry free and truly enjoyable. And I loved that because I travel the world full time with Carry-on Luggage only. And so, I really appreciate that. For people though that are not yet on team Carry-on and would like or aspire to potentially get there. Can you share some tips? And I think both maybe from your perspective, but also what your wife might say to the women listening out there as well on how to travel the world without checking a bag.

Darren Chew: So, my biggest tip that I tell people is leave it at home. Anything that you want, generally speaking, you can find. And there’s things that you realize that you think that are essential that are really not essential. I’ve never been somewhere and been like man, I wish I had this before. If I do need it, I go to the store and I’ll get it. Granted, that’s my perspective. There’s not much that I need or want my travel for the experience and not the other things. But that is my perspective. My wife is a woman and she is not as much of a minimalist as I am, but I am blessed beyond measures that she also has joined me. And not just in carrying, she just travels with book bag. We went on our honeymoon; we went all these places with just a book bag. Also, it does help that I travel so minimally that she puts a lot of stuff into my bag. But we both have two book bags.

So, what I would say is there’s a lot of different ways that you can minimize the things that you have. The first thing that you realize is you go through your stuff. And what I do with my wife is there’s ever outfits that she brings that she does not wear. She’s never able to bring that outfit again because it just wasted space in her luggage. So, it’s just being strategic. My wife is a type A planner so she always wants to have things just in case. So, all her outfits are planned before the trip. She knows where we’re going to go and she knows that this outfit will be good with this place. And this helps because she’s not bringing extra stuff because she knows what she’s going to wear, she knows what she’s going to see and if there’s anything else. My wife loves to shop. She’ll go shopping. So, the only thing that I feel like is nonnegotiable or difficult for her as a black woman is finding hair products.

We go to certain places that just will not have black hair care. So, some of those things can get challenging in terms of keeping her hair moisturized and letting her style her hair. And if she ever does have a really long trip, what she does is normally just braid her hair. It makes it easier for her to manage and she doesn’t really need much in order to take care of it.

Matt Bowles: Well, you and your wife do an amazing job of documenting your travels on your YouTube channel ChewsToExplore, as well as your blog and your website and your social media and all of that. Which raises my next question that is, as someone that consumes your content and follows you, I really appreciate the amount of effort that goes into the drone footage and showing how gorgeous these places are, and then you and your wife showing what you’re doing and giving your feedback and your tips and your advice and the videos and all that kind of stuff. So as a traveler and as a consumer of your content, I love that. I’m asking you, though, behind the scenes for you and your wife, how do you balance documenting the experience, getting the footage, creating all that amazing content, with actually being present in the moment, having the travel experience yourself, and actually living it.

Darren Chew: So, the biggest thing that I would say with that is that we enjoy creating content. It is not a chore to us. It is fun and we both are on the same page with it. We know how blessed and we are so grateful to have the experience that we have. And we know that so many people, especially like people in America, have not had the experiences that we have had. So, I wouldn’t say that we feel like we owe them to show these experiences, but we want to show our experiences. We started creating our YouTube channel because so many people would ask us, what is this place like? What is that place like? And rather than telling them, we put things together to show them. So basically, our YouTube started as a digital scrapbook for us. We just did it not for views, not to make money, literally, just to show people what our experience is. And also change people’s perceptions around what travel is like and how you can also do it affordably, relatively speaking.

So, through the years, I think this year makes four years we’ve been on YouTube. We have been able to have a good idea in terms of what we need from a specific shot, a specific place, a specific anything so that we’ll go somewhere. And because we know we need an overhead shot, we need a coming in shot, we need to talk about the food, the price, and how it made me feel. It’s relatively easy because we know what we need before we go into the places. So, I guess planning and being detailed will save you a lot of time. But I think the biggest thing is really that we enjoy it. It’s not a chore. It’s taking you guys along the journey with us. And when we get amazing shots, we’re like, wow, I can’t wait to show you. It’s like. Like, you guys can see how amazing this is too.

Matt Bowles: Yeah, I love that, man. So, for couples, let’s say, specifically who might be at the earlier stage of traveling together, as you said, it can be an incredibly enriching experience for relationship, but it can also have issues raised to the surface that maybe didn’t come to the surface when you weren’t traveling. So, I’m curious, any tips that you might have for couples that would like to do more traveling together?

Darren Chew: For sure. So, the biggest thing is compromise. Okay? You guys want to be on the same page, and that’s many different things. My wife and I are so different in the way that we travel. My wife loves beaches. She loves pina coladas. She loves hanging out on the beach. If she could, she would spend the whole day on a beach. Me, I go to a beach, I step on the sand, I look at the water. I said, this is great. And then I can go. I say, what else is there to do here? But it’s all about compromise. So, whether it’s a destination is a compromise. You go to someplace that has many different things, or you have one day of relaxing, one day of adventure, one day of history that you both can compromise and have experiences with, that is the important thing in terms of finding that balance between the relationships. And if you guys are both on the same page, then it’s even better because there is not much of a compromise. But it’s just really about communication and understanding in terms of relationships.

Matt Bowles: All right, Chew, let me ask you one more question, and then we’ll wrap this up and move into The Lightning Round. You have now traveled to over 60 countries. You’ve been doing this for many years. Why are you so passionate about continuing to travel? At this point in your journey, what does travel mean to you?

Darren Chew: It’s just the feeling that I get when I’m in a new place and a new experience. And it’s just like getting me out of my comfort zone, seeing people trying food. At this point in my life, I’m still so curious. There are still parts of my life that I have not even found out yet. And a lot of these experiences getting out of my comfort zone, I learned through travel. I learned that I like these things. I learned that I don’t like these things. And I hope that I will stay curious for the rest of my life.

Matt Bowles: All right, well, I think that’s the perfect place to end the main portion of this interview. And at this point, Chew, are you ready to move in to The Lightning Round?

Darren Chew: I’m ready.

Matt Bowles: Let’s do it. All right, question number one. Are the New York Knicks going to win the championship in 2026? Is this the year?

Darren Chew: This is absolutely the year. Listen, the Knicks were taking it and we’re winning it in five games.

Matt Bowles: Folks, you heard it here. And Chew is going to have receipts when that comes to pass later in 2026. All right, what is one book that you would recommend that other people should read?

Darren Chew: I read a book by Dave Ramsey. He’s the person that kind of put me onto financial freedom and being financially savvy. And The Total Money Makeover by Dave Ramsey was an eye opener to all thing’s money to me.

Matt Bowles: All right, who is one person currently alive today that you’ve never met that you’d most love to have dinner with just you and that person for an evening of dinner and conversation?

Darren Chew: This might sound a little cheesy, but I want to say Barack Obama. And I say that because I feel like outside of being the first black president and all those things, I feel like he is such a well-rounded person and he knows so many different things and it would be amazing conversations for sure.

Matt Bowles: All right, knowing everything that you know now, if you could go back in time and give one piece of advice to your 18-year-old self, what would you say to 118-year-old Chew?

Darren Chew: Stay curious.

Matt Bowles: All right, of all the places that you have now traveled to, what are three of your favorite destinations you would most recommend, other people should definitely check out.

Darren Chew: Of course, I have to say Jamaica. I’m going to also say Rio de Janeiro. As we spoke about it highly enough. It’s an Amazing place to be. And one experience that I think that everybody should do is to go to Namibia. Namibia is one of my favorite places I’ve been to as well.

Matt Bowles: Love that. Do you want to give a shout out to Namibia and just say what you loved about it that was so special.

Darren Chew: My wife and I rented a 4×4 camper and we went throughout Namibia. It’s the second least densely populated country in the world. And it was just my wife and I in a camper. The most amount of stars I’ve ever seen in my life. The wildlife here, the sand dunes, the beaches, the food, the culture. My words aren’t going to describe it. Watch our YouTube video on it because you will see how amazing this country is.

Matt Bowles: We will link up your YouTube video on Namibia in the show notes so folks can go and see that. And then, of course, Jamaica, I’ve got to get your recommendation for people that would like to experience Jamaica beyond a standard tourist experience in Jamaica. What would you recommend? How should people experience your country?

Darren Chew: Jamaica is amazing because it is so diverse. In my home parish of St. Elizabeth, one of the best things that if you are into history, especially Black Liberation, is there are people called the Maroons in Jamaica. And the Maroons are from the mountains. What they did, they were one of the first people to revolt against the British. And the Maroons actually had a treaty with the British prior to slavery even being abolished. There was experience we had in maroon town in St Elizabeth, where we got to learn about the history, learn about the culture, their ties back to Africa, how they were strong people and were able to fight off the British army, which was at that time one of the of the best armies in the world.

Matt Bowles: All right, Chew, what are your top three bucket list destinations, places you have not yet been highest on your list you’d most love to see?

Darren Chew: I definitely want to go to Ethiopia. I love the idea of Ethiopia because of places in Africa. It’s the only one that was not colonized by a European invader. Especially with my Jamaican ancestry, the ties to Ethiopia are astounding. And it’s definitely a place that I want to go and spend a lot of time in. In that same breath, I want to visit Haiti and have an actual experience in Haiti because once again, that Black liberation, the story that they were able to revolt against the fresh army and have the first free country in the Americas and inspire even the United States of America at that time. Also off of that train, I definitely want to visit Socotra in Yemen. I want to see the Blood Dragon Trees. I want to experience it because a lot of people give Yemen such a bad rep. But it is a lot of beautiful things to have you where you go. And that’s such a unique thing to see as well.

Matt Bowles: 100% shout out to the people of Yemen as well. All right, Chew, we have now come to the most important two questions of this interview. I’m about to ask you to name your top five hip-hop emcees of all time. And I’m going to ask you to name your top five Jamaicans dancehall artists. Let’s start. Before you name your five. When we go into that, can you just share a little bit about what music has meant in your life, specifically Jamaican dancehall and hip-hop and how you connected with those art forms and what they mean to you.

Darren Chew: Being raised in New York, music is such a big part of it. Anywhere you go, anywhere you see, it’s just live music, whether it’s the people walking down the street with a speaker on their shoulder. You’re on the train and you’re trying to tell somebody to shut up and turn their music off. People walking around handing you, their CDs. Music is such a big thing here in New York, especially being such a diverse place and the influx of immigrants. You learn so much about people and their culture. And then also when we talk about dancehall, the interesting thing actually, my mother, even though I am Jamaican, my mother grew up not listening to any dance. I didn’t really listen to dancehall until I started going to parties. Because in New York, if you go to a party and they don’t play dancehall, if they play anything else besides dancehall, now, they play Africa Afro beats, too. But if you go to a party that doesn’t play dancehall or doesn’t play Afro beats, nobody’s going to the party. There’s no party without having those.

Matt Bowles: Well, as you know, I was a hip-hop DJ in the 1990s, and in my opinion, that’s when the best hip-hop ever was coming out. And it was coming out of New York. Like, for me, 1990s East coast hip-hop is my love language, my heart and soul. But at the same time, the 1990s Jamaican dance hall that was coming out was unbelievable. And then you had this incredible crossover where you had people like Super Cat that were putting Biggie on the tracks. And then you had KRS-One doing stuff with Mad Lion. And then you had all of this intermixing of the New York City hip-hop with the Jamaican dance hall. And it was like the most unbelievable thing and so forth. For me, those genres are so special and they’re so meaningful. So, without further ado, let’s start with the Jamaican dancehall artists. Who are your top five?

Darren Chew: For sure. I got to put Buju in there. I listen to a lot of Buju. I listen to a good amount of Vybzs. I got to put Vybz in there. I got Popcaan, for sure. I got Gyptian. I’m going to throw Beenie Man in there just because I listen to a lot of Beenie too. I can’t miss Beenie.

Matt Bowles: Amazing. All right, and so the very final question of this interview. Top five hip-hop emcees of all time.

Darren Chew: First, I got to put Jay Z. I’m New York. My artistry right here is going to be very New York. Jay Z. I’m also putting Nas in there because these are two top tiers also growing up, elementary school, middle school, 50 Cent. I got to put 50 in there. Even though he doesn’t have the large catalog of everybody else, 50 in this top is in his prime there. Now this maybe I’m talking about a non-controversial Kanye West. I’m talking non-controversial. And then I’m throwing DMX in there because I really, I grew up on a lot of DMXs. Still New York hip hop. Yeah, that’s my five. I’ll stick with it.

Matt Bowles: All right, amazing.  Chew, at this point, I want you to let folks know how they can find you, follow you on social media, check out your YouTube, your blog. How do you want people to come into your world?

Darren Chew: For sure. So, my wife and I have many platforms. On every platform, it’s ChewsToExplore. That’s on YouTube. That’s on Instagram. We have TikTok. We have other platforms that we have threads. Any platform that you guys use, we’re on. And it’s ChewsToExplore.

Matt Bowles: And you also offer some incredible free things for people when they come onto your site that they can grab. Because you guys do an amazing job, I think of, number one, profiling different places so people can actually get a visual. They get amazing drone shots and they can see what places look like. But then you also give them tips and hacks about, like, stuff I wish I knew before I went to this place. And you give them like the 10 things they need to know if they’re going to plan a trip there. So, I think you’re saying is really, really good for trip planning. First of all, picking out, where would I want to go? Let me see. What does Sri Lanka look like? What does Malaysia look like? What does this place look like? And then, ooh, okay, yeah, I want to go there and see that. Then you have a separate video that’s here’s 10 things I wish I knew before I went there. So now if you want to plan your trip, you help them plan the trip. So, a lot of that stuff is just through your videos, but then talk about some of the special offers that people can opt in for and get totally for free for sure.

Darren Chew: Absolutely. Our website is the number one place that you guys can find resources for as you said, trip planning experiences. A lot of people I know read blogs and blogs are on chewstoexplore.com is the best way to do it. We also have information about going places, about how if you are interested in travel hacking, using points in order to travel, it’s on our website. Destinations, places that we want to go. The website is a one stop shop for basically all things travel and also for staying connected with us as well.

Matt Bowles: Yeah, it’s a trove of free content folks. They go a lot deeper on some of those points and miles and smart travel strategies that we discussed in this episode. So, you can go out in for some things, get a whole bunch of cool stuff and just check out the amount of content that you have on your YouTube and everything at this point. It’s just amazing. I’ve gone through a lot of it and it’s really, really top notch. So, we are going to link all of that up in the show notes. You can just go to one place at themaverickshow.com, go to the show notes for this episode. There you’re going to find direct links to everything we have discussed on this episode, including all of the ways to find, follow and connect with Chew.

Brother, this was so amazing. Thank you so much for coming on the show. It was great to have you here.

Darren Chew: Thanks for hanging out with me for a couple hours here. I appreciate you, my brother.

Matt Bowles: All right, good night, everybody.