the vip lounge | desi oakley

Vacation is all about relaxing for ‘Waitress’ star

Actress Desi Oakley on the beach in Mexico.
Actress Desi Oakley on the beach in Mexico.

Desi Oakley said that while Tulum, Mexico, “stole my heart,” she can’t wait to go to Paris and practice French, which she once spoke fluently. Oakley, 28, is coming to Boston as the lead character in the musical “Waitress” (Feb. 20 through March 4 at the Boston Opera House) and she couldn’t be more excited. “I’ve never been to Boston, but everybody says it’s amazing,” she said. “I saw it on our tour list and I flipped out.” Based on the movie of the same name, “Waitress” tells the story of Jenna, a waitress and talented baker who enters a pie-making contest in hope of getting out of her small town and loveless marriage to an abusive man. Oakley, who has been in three Broadway shows — “Wicked,” “Les Miserables,” and “Annie” — and is now on her third national tour, was born and raised in Wichita, Kansas, and now calls New York City home. We caught up with the accomplished performer to talk about all things travel.

Favorite vacation spot? Tulum, Mexico, stole my heart with the combination of beautiful beaches, five-star restaurants, and opportunities to relax the mind, body, and spirit. I can stroll on the softest sand beaches after a hot yoga class with a green juice in my hand — and that is the epitome of vacation to me. Tulum is like a hip corner of Brooklyn on the beach.

Favorite food or drink while vacationing? My favorite drink on vacation is a French 75: Gin, champagne, and a twist of lemon — no simple syrup for me. [It’s] perfectly refreshing, and the bubbles make it celebratory.


Where would you like to travel to but haven’t? Paris, France. After finishing the National Tour of “Evita,” my best friend and I had a trip planned to visit, but we were set to land only 18 hours after the terrorist attacks in 2015. We ended up canceling our entire trip. I still can’t wait to taste the baguettes and sip rosé on the cobbled streets. Plus, I used to be fluent in French. I’m looking forward to it.

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One item you can’t leave home without when traveling? To be practical? My adjustable eye-mask. To be daring? A bold lipstick.

Aisle or window? Always window. When I fly, I’m reminded of how small I am. The view above the clouds will always be majestic to me.

Favorite childhood travel memory? Going to the beach with my family. When I was 8 or 9, I used to fear the ocean. It was so big and powerful and I couldn’t comprehend the inconsistency of the waves. My sister, Rebecca, used to drag me deep into the water. She would hold my hand and tell me to trust her. I would squint through the cold bursts of spray in my face as my body was forced to surrender to the weight of the tide. The farther we went, the calmer it was. Those moments made me.

Guilty pleasure when traveling? Taking the phrase “It’s 5 o’clock somewhere” very seriously.


Best travel tip? Live like a local. Skip the tourist attractions and dive deep into the culture.