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Akaash Singh loves India, but said he is itching to go to the Maldives on his next trip abroad. The Indian-American stand-up comedian, actor, and podcaster — who cohosts the popular “Flagrant” podcast with Andrew Schulz (on YouTube with more than 1 million subscribers) — is bringing his edgy comedy show to the Wilbur on Jan. 14. “I can’t wait to get to Boston. I love the city — outside of the weather,” said the 38-year-old Dallas native in a phone call from Punta Mita, Mexico, where he was vacationing with his wife, Jasleen. While admitting that he pushes the envelope on the joke front, he does so unapologetically. “I think there are fewer and fewer comedians who are willing to make laughter out of things that are otherwise uncomfortable. I am not disrespectful, but I like to laugh at things that people are not supposed to laugh at in society. People are able to do that at my show.” We caught up with Singh, who lives in New York City with his wife, who is working toward her master’s degree in business journalism, and their 5-year-old Maltipoo, Happy, to talk about all things travel.
If you could travel anywhere right now, and money was no object, where would it be? It would be a two-leg trip: first would be to India. I love Bangalore and Mumbai and also think Chandigarh is amazing, but would also love to see Kerala in the south. I’ve heard it’s amazing. Wherever we go, afterward I would stop by the Maldives before going back to America. I’ve heard it’s amazing and as much as I love India, it’s exhausting.
Where was the first place you traveled to after COVID restrictions were lifted? I gave quite a few people COVID on Thanksgiving 2020 — apologies again to Colin Quinn — the silver lining in that awful cloud, though, was we were immune before the vaccine. So our entire podcast — to whom I also gave it — headed down to Miami during lockdown. And after nine months of being locked down, seeing other people and escaping the constant cloud of COVID was one of the happiest times of my life.
Do you prefer booking trips through a travel agent or on your own? I always booked on my own, but now I got a great Indian travel agent named Sudeep Shah. If you travel a lot, especially for work, it’s very worth it. I had to miss two shows in Tampa in March because I had multiple flights canceled. Ever since then, I’ve been Team Travel Agent.
Thoughts on an “unplugged” vacation? I wish I could live an unplugged life. One of my life goals is to continue climbing in my career, eventually reaching a point where I no longer need my phone for work. I would give my iPhone to someone in need or do us both a favor and flush it down the toilet.
Do you use all of your vacation time, or leave some on the table? When you work for yourself, you typically work seven days a week. However, when there are a couple of days/weeks when things shut down — typically the last two weeks of the year — we take it.
What has been your worst vacation experience? For our one-year anniversary, I took a quick trip to Chicago with my wife. But health issues got in the way and she couldn’t do anything — at all. It was brutal for her, and seeing her go through it wasn’t great either. Our anniversary dinner was my wife lying in bed and me eating room service alone, watching TV on my phone so I wouldn’t wake her up.
Do you prefer vacationing to relax, to learn, or for the adventure of it all? It depends on how busy I’ve been. If super busy, I don’t want to do anything. If not, let’s see the world.
What book do you plan on bringing with you to read on your next vacation? On my way to Mexico now and taking the book “Sapiens: A Brief History of Humankind.” I barely read now because of this stupid phone though, so hopefully I can make a dent in it.
If you could travel with one famous person/celebrity, who would it be? Forget celebrities. I just want to convince my mom to take a trip.
What is the best gift to give a traveler? It depends on where you’re going. To France: a pocket translator. To India: toilet paper.
What is your go-to snack for a flight or a road trip? If I’m trying to be healthy, protein chips or turkey jerky. If I’m being a real human being, anything else.
What is the coolest souvenir you’ve picked up on a vacation? I used to buy mugs and magnets. Now I think souvenirs are fairly stupid. My house [has] got enough crap I don’t need. Why collect even cheaper crap that I need even less?
What is your favorite app/website for travel? Hotwire hot deals. But if I can’t get a hot deal, it’s all the same.
What has travel taught you? Go! Go everywhere. Live in different places. Experience every culture you can. The world is so much bigger than you think. See it all.
What is your best travel tip? I went to India in 2019 with my wife for our engagement and it was amazing. Also, the first time I went to Europe I saw Rome. And I remember when I saw the Colosseum — this thing I learned about in school but never cared about — I realized why people travel. Seeing things is so, so much different than reading about them. And as obvious as that sounds, you kind of have to experience it to really realize it.
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