Well-Traveled: Globetrotting Stiletto

Metanoya Webb

If you like to see someone travel in style, Metanoya Z. Webb a.k.a the Globetrotting Stiletto is your girl. This NYC-native’s wardrobe is always on point with colorful dresses, perfect sunglasses and a mean shoe game. We’ve followed Webb around the globe from Bangkok to the Cayman Islands to Sicily where she’s shown us gorgeous locales and, of course, great looks. Find out how she initially got into travel blogging and how she navigates traversing the globe.

What was your first memorable trip?
Metanoya Z. Webb: My first impactful travel memory is going to do Missionary work in Puerto Rico when I was 13. What made this trip so memorable was that it was my first introduction to traveling on my own, without my parents. They trusted me to go with a church group and do my own thing. We were doing missionary work helping underserved communities in Loiza, a predominately black town in Puerto Rico. Through that experience, I learned that I was okay traveling by myself, and I think that helped shape my confidence to go study abroad in college.

Where did you study abroad?
I studied in London — that experience helped me develop my independence even more. I had a chance to hop around Europe; I could just get on the Eurostar and see all these different cities for super cheap on my own. For me, that dispelled the notion that travel was expensive. I realized that there were ways to do it economically and that you don’t have to have a ton of money to be able to see places and do things. I would say that those two experiences helped shape and inform my travel perspective, it helped show me how accessible travel was and that I want to continue to do it forever.

Metanoya Webb

When did you decide that traveling was something you could do for a living?
I have a traditional publishing background. I worked for magazines and then as the industry started to evolve I followed in the footsteps of some of my mentors who had pursued lucrative contracting and freelancing opportunities. When you’re a contractor, you have a little bit more flexibility, you can work remotely. It was then that I realized that I could do that and also travel on the side to make money. I did partnerships with different brands, it just happened organically. I went to TBEX one year, which is huge, it’s the best resource for travel bloggers or travel professionals who want to do things on a larger scale, get branding and secure funding. As a travel writer, you’ll get a good trip and you have this luxurious, awesome experience but how does that translate to dollars and cents? You’ll find many travel bloggers and writers, who aren’t as “successful” monetarily as you would think. I was intentional about the different opportunities I would take. I made sure to hook up with a variety of blogger networks and do partnership opportunities through them. These things weren’t paying huge money, but if you do enough of them on a consistent basis it can supplement your freelance income.

Why Globetrotting Stiletto, what does that mean to you?
Back in the day, I loved stilettos. I’m a mom now and very rarely walking around in my five-inch heels, but there was a time when that was my thing. I was sitting down with a girlfriend talking to her about wanting to brand what I was doing and we came up with that name. I think it’s relatable to a lot of women out there. To me, Globetrotting Stiletto caters to women who are very fashion-conscious, who don’t mind splurging on experiences. I don’t mind spending the extra money to really make sure that my experience is worthwhile. Globetrotting Stilettos like to put thought into their looks before they travel because that part matters too. GTS caters to fashion and style-savvy women who really are committed to making travel a prominent part of her their lifestyle.

Metanoya Webb

What’s a place that you would love to visit again and why?
I would love to go back to Croatia. What made that trip so special is that I didn’t know what I was getting into. One of my close friends’ sorority sisters is half Croatian, so her father and father’s family still live there. We had such an authentic amazing experience! We stayed in Nedešćina, a small village in Istria and rented a guest house which is very popular in Europe. AirBNB because wasn’t even a thing back then. We had wine delivered to us several times a week in recycled two-liter bottles. We were in wine country so we got the wine before it was formally packaged and distributed — family-style. We had red wine, white wine, and dinners every night, it was perfect. It was not your typical touristy vacation at all. We all felt like we were like submerged in the culture for the two weeks that we were there. What made this trip so special was sisterhood. To have five or six professional black women stepping through the streets of the former Yugoslavia before yacht week was a thing and brown folk had zero interest in that region of the globe, is major!

Does being black affect your travel experience, if at all?
I think my perspective is a little more evolved because I grew up in a household where my mom was an educator (she’s a retired NYC public school principal). My siblings and I were taught to be proud of who we are and not to shrink because of the color of our skin. So traveling while brown is something I never even thought about when I embarked on this journey two decades ago, I just wanted to go! Being a black woman wasn’t and still isn’t a deterrent for me. My mom always said that most times ignorance comes from a lack of understanding. It was interesting when I was in Croatia — we could tell they weren’t used to seeing black people. For someone else it that might be offensive to have young boys staring at you bemused, but I took that as an opportunity to educate. Like you don’t know me, so this may be one of your few encounters with a black person with kinky hair, a round face and a whole lot of curves. I want this to be memorable for you in a positive way, so I took that opportunity to just let them learn. It was a special moment. I don’t think I’ve ever really felt unwanted in any country anywhere that I’ve visited. It was more situations where I could tell that they weren’t accustomed to seeing people like me or people like us.

What’s the most photogenic place you’ve visited?
Brazil is beautiful. The landscape is stunning great; Rio is amazing and it wasn’t until I was visiting that I remembered they have quite a few Wonders of the World. I love Jamaica, that’s where my family is from. It never gets old, every time I visit, I’m always in awe. Costa Rica is another place that is really magical—the rainforest, the beaches, everything is great. Both the Caribbean and the Pacific coast of Costa Rica are super photogenic.

What’s your travel advice for somebody who maybe isn’t a seasoned of a traveler as you?
Just go explore! Don’t be afraid to throw away your itinerary and just roam. Don’t be afraid of the locals and don’t be afraid of doing things that are off the beaten path. There’s so much more to see in destinations other than what’s publicized and or reported on. Sometimes the best way to get an enriching experience is by wandering, getting lost and talking to strangers. I think people are so afraid to talk to strangers when they travel, but you never know who you will meet and what they may able to offer you and your experience. Of course, being safe and cautious as a woman is important if you are traveling alone. But still, you should talk to people, really interact and be respectful of cultures. I think that sometimes Americans we can be arrogant and obnoxious when we travel. We just want to bring our culture to and just drop it in a different environment. I try to be conscious of other countries’ customs and respectful of their way of life.

Metanoya Webb

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