Go Away With … Kendra Cunningham

By Jae-Ha Kim
Tribune Content Agency
August 29, 2017

Stand-up comic Kendra Cunningham, who holds a master’s degree in forensic psychology, has appeared on shows such as “Saturday Night Live” and “Mom’s Night Out” and enjoys bartending when time permits. She is also the author of “Blonde Logic” and has released a comedy album of the same name. For more information on Cunningham’s projects and live dates, check out her website and Twitter account.

Q. What is your favorite vacation destination?

A. Cape Cod, especially Dennis Port. My family has been going there for years and it’s a less populated area on Cape Cod in the summer than some of the bigger towns.

Q. To someone who was going there for the first time, what would you recommend that they do during their visit?
A. Get fried clams at Sesuit Harbor Café. Rent a canoe at Cape Cod Waterways. I highly recommend the Ocean House Restaurant, which is right on the water on Depot Street. The food is consistently on point, the view is amazing and there is always a fun social scene at the bar. Always! No matter what time of day you show up, people are having a good time and are eager to draw you into it. The also have a Tiki Bar outside overlooking the beach, where you can get the upscale food from the Ocean House in a laid back setting. It’s the perfect place to watch the sunset. You can stay at the Three Seasons. My mother worked there. They did the place over a few years back and it’s pretty cozy. They have a pool, but it’s usually filled with kids. You can get rooms that open up right to the beach. If you want to bring your dog, Sea Shell Motel is right down the street and also has rooms opening up onto the beach.

Q. Where are your favorite weekend getaways?

A. Living in Brooklyn, my favorite weekend getaways usually involve a lot of open space and nature. Getting to a beach in Long Island and renting a B&B, Bear Mountain, Woodstock, Beacon. Puerto Rico is a great one, too. It’s not that long of a flight and the Puerto Rican culture is so rich.

Q. What was the first trip you took as a child?

A. The first trip I remember was to Walt Disney World in Florida. I remember loving the rides, but I got sun poisoning on my face. My face swelled up and was really itchy. My family had to bring me to the hospital and I felt like I ruined the trip.

Q. What’s the most important thing you’ve learned from your travels?

A. Traveling has taught me that you can live your life however you want to live it. There is probably somebody somewhere with the lifestyle you want. The only difference is they did it. Everybody has a story and a wish.

Q. Where have you traveled to that most reminded you of home?

A. I still think of Boston as home, even though I’ve been in New York City for over a decade. Chicago reminded me a lot of Boston. Boston is a pretty contained city. You can walk to a lot of different areas and not get bored.

Q. Where is the most romantic destination?

A. Mykonos. But I was with my mom and my sister, so I have to go back with a man.

Q. If you’ve ever gone away for the holidays, which was the best trip?

A. One year, my mom, my sister and I went to Playa del Carmen for Thanksgiving. It was such a great way to spend the holiday. We went for five days. We went to Tulum, held monkeys, rode a donkey, played tennis. … It was the most action-packed five days. We did not have turkey, but we didn’t care. We befriended a handsome tennis pro who came to dinner with us on Thanksgiving. Every year since, I advocate for travel on the holidays.

Q. What are your favorite hotels?

A. I’m a big fan of the Kimpton Hotels. Now it seems like there are more and more boutique hotels popping up. I remember reading an article about Bill Kimpton and how hard it was for him to convince people that his vision for boutique hotels would work. Underdog story.

Q. What are your five favorite cities?

A. Boston, New York, Milan, Amsterdam, Kilkenny.

Q. Where would you like to go that you haven’t traveled to yet?

A. I want to go to Eastern Europe — Lithuania, Poland, the Czech Republic, Croatia. My grandmother came to the U.S. from Lithuania and she was a cool lady. There is something about Eastern Europeans that seems honest, but secretive at the same time. I would like to be immersed in that.

Q. When you go away, what are some of your must-have items?

A. I have to have water, moisturizer, sunscreen, my notebook and nice bedding

Q. What would be your dream trip?

A. Extended travel. I’ve never traveled for more than two weeks. I would love to travel for a month. Maybe even live in another country for a while. I’d love to check out India for a bit. Right now I am really into tarot cards, yoga and spiritual enlightenment.

Q. What is your guilty pleasure when you’re on the road?

A. Spa services. I like to get a massage or a facial, especially after a long flight. I need to have soft luxurious bedding. I have been known to buy sheets for the B&B I rented.

Q. What kind of research do you do before you go away on a trip?

A. I research things to do, restaurants, vintage clothes stores, if there will be any comedy or musical acts I want to see, museums. I like to see if there are any town fairs going on or city celebrations.

Q. What is your worst vacation memory?

A. The worst trip I ever took was with my family. We went to Maine. We got there and the hotel was really scary. Light fixtures missing bulbs, people hanging out in the hallways, the rooms seemed dirty. We barricaded the door, but we never made it through the night. We packed up around 2 a.m. and drove home.

Q. Have you traveled to a place that stood out so much that you felt compelled to incorporate it into your work?
A. As a comic and a writer, there have been places that I travelled to that inspired me so I feel as if I incorporated them into my work that way. There are also a bunch of places I’ve been that I think, “I want to shoot a movie here.” Location can tell a story on it’s own.

© 2017 JAE-HA KIM
DISTRIBUTED BY TRIBUNE CONTENT AGENCY, LLC.