What makes Puerto Rico such a special place to visit?

I would encourage any tourist going to Puerto Rico to check out what’s playing at the Pública Espacio Cultural, a cultural center near San Juan. They’ve always got two or three shows going at the same time. Even when we were doing “Hamilton,” there was a kid’s show that we were sharing a dressing room with, and it was wonderful to get to know them while we were all getting ready to do our performances. It’s a bustling cultural center. Also, there are incredible museums in San Juan, and we’ve been partnering with Google Arts & Culture to digitize the art there so that wherever you are in the world, you can see these sixteenth- and seventeenth-century paintings from Puerto Rico. It was very different then from how it is now, and you get amazing glimpses at Puerto Rico’s artistic history from seeing that work.

Another thing we have done as a family that I really enjoy is work with an organization called Parguera Eco Tours. There’s one in Fajardo where you get to see the bioluminescent bay, but you do it in an eco-friendly way. Because if you’re all jumping in there with your hairspray and your suntan lotion, it harms the bay. And so it’s an ecologically responsible way to experience that incredible phenomenon.

If you know nothing about Puerto Rico, but you’re a fan of mine, my uncle and my family in Vega Alta, our hometown, have created this placita [small square] in our hometown named after my paternal grandfather, Abuelo Wisin. It has a big mural of him, and there’s just amazing coffee and food, and then there’s a gallery nearby of my stuff — my Grammys and my awards. We send that all to the museum down there. So there’s this little corner of the world where my family came from, and it sort of charts our journey. It’s very surreal for me because my grandfather owned that little corner and every summer it was often a different business. Sometimes it was a restaurant. My favorite years it was a video store, Miranda Video, and now it’s dedicated to him because he made small businesses work on that corner for so many years.

What was a particularly transformative travel experience?

One of the more transformative travel experiences I had was actually a chorus trip my senior year in high school. Our high school jazz chorus went to Senegal to sing, and we were those kids selling candy in the subway to raise money for our travels. We sold Reese’s Peanut Butter Cups, Snickers, and those cheap box sets, and then we went to Senegal and got to spend time with students at the University of Dakar. The really transformative experience was that the common language we shared with them was hip-hop. We had nothing in common. They were older than us; they came from a totally different country on a different continent, and yet we were all fluent in Biggie and Tupac and we were all singing those songs together by the end of the night. So that was an amazing education about how music transcends boundaries at a very formative age. Whether it’s Mexican goths who love Morrissey or English-speaking kids who are all at the Bad Bunny concert — music transcends language, and it transcends culture. It’s always remarkable to see that.

Your work often engages with history. What has been a valuable history lesson for you?

One of the first books I picked up during the pandemic was “Will in the World: How Shakespeare Became Shakespeare.” I was like, all right, we’ve been through plagues before. Let me go read through what it’s like to live through plagues and be an artist living through plagues. So I picked up this book and sort of figured out what Shakespeare did while he was writing plays, and the theater kept getting shut down because of plagues. Because that felt analogous to the moment we were in. I have often looked to history to try to make sense of the moment we are in. And I was not a history buff prior to writing “Hamilton.” I think it’s important to say that because people will come and start talking to me about some American era, and I am like, Oh dude, I learned just enough to write my show. I’m like the substitute teacher who just read the syllabus and took the parts that I thought rhymed and presented them to you.

But for me, because Hamilton was born in the Caribbean and was the proto-immigrant of the founding era, that was my way in. That was my way of being like, I understand this guy. I can’t get my head around the whole thing, but I understand this guy and his energy and his momentum. And that was my key to being able to dramatize it. And I think that’s what great writers do and what great biographers do — they make us understand someone. I felt the same way when I read “Team of Rivals” by Doris Kearns Goodwin. Lincoln’s impulse to bring the people he ran against into his cabinet to be like, “I’m going to need these perspectives,” and to understand how rare and valuable that was. So yeah, I wish I had a great book recommendation to make sense of this moment, but I don’t. I’m muddling through the best as anyone else. That book is maybe yet to be written.

What is the best neighborhood in the world to wander around in?

I’m going to say my neighborhood, Washington Heights. I’m still there, and I’m still wandering around.

What’s the best gift you ever brought back for someone from a trip?

Oh, I can tell you about a failed gift. My dad bought a bottle of ’54 Port when we went to Portugal when I was a kid. When I was 13, my mom used it as cooking sherry by mistake. It was the worst fight they ever had. Years later, when my wife did a semester of her law school in Spain, one day she looked at me and said, “Let’s go get cheap Ryanair tickets to Portugal. Let’s go find that ’54 Port.” So we went. We never found it. We came back empty-handed, but it was a great trip anyway.

What do you always take with you on any travel adventure?

My wife makes fun of the fact that I buy so many neck pillows. I have an entire household filled with neck pillows and I always leave them at home. Then I buy more of them at the airport. So she would probably say that. But, honestly, the most important things to remember are your chargers.

Header image: Photography by Mark Hartman