Cruise with Oprah Winfrey: What It's Really Like

Oprah Winfrey walks into a bar. In her pajamas. And gives everyone a free shot of tequila.

No, you are not dreaming. You are on the Oprah Magazine Girls’ Getaway cruise.

And yes, you are living your best life.

The three-night, four-day cruise, which set sail from Ft. Lauderdale and sailed to the Caribbean, was the most recent entry in the ongoing partnership between Holland America and O, The Oprah Magazine. For about $750 per person (more for a suite, less for an inside cabin), guests aboard the brand-new Nieuw Statendam ship were treated to an experience that can best be described as deep-diving into the pages of O.

Naturally, there is much to love about cruising with Oprah, so let’s break it down into a few of our favorite things, shall we?

1. Oprah. This cannot be overstated: Oprah is with you. On the boat. This is not the case with every Holland/O cruise — but for the Bahamas cruise she didn’t miss a moment. Even better, she roamed the ship like any other sunglasses-wearing passenger, which added an element of surreal surprise. Working out in the gym before breakfast? Oprah might just be on the treadmill next to yours. Savoring a steak dinner in one of the ship’s restaurants? Oprah just might appear to blow out candles on her 65th birthday cake. Listening to live music at the bar? Oprah might stroll in AND GIVE EVERYONE TEQUILA SHOTS.

2. Half Moon Cay. The private island where the Nieuw Statentam anchored for daytime excursions featured everything a tropical escape could need: glass-bottom boats, snorkeling, white sand beaches, blue skies and rum runners. Also, Gayle King on horseback!

3. The O Shop. This pop-up shop features curated products from the O List, custom pajamas (what else would you wear to drink tequila with Oprah?) and items from O, The Oprah Magazine’s new Talbots collection. In other words: all the favorite things.

4. Book Club. Billed as “O’s Reading Room,” the conversation with Tara Westover — author of the best-selling memoir Educated — was akin to joining Oprah’s book club in person. O Magazine books editor Leigh Haber had been scheduled to interview Westover, but in a surprise switch, Oprah herself did the honors. Turns out, she’s a pretty good interviewer.

5. The Feelings.

You know Oprah. You know her story. But you have never felt Oprah like this. During “A Conversation with Oprah,” the guru unspools her journey from a poor, brilliant child growing up in rural Mississippi to budding journalist to insecure actress to billionaire master of the universe. She shared what she has learned along the way, including advice on life, love and loss. There were hundreds of acolytes in the audience, and oceans of tears. I’m not a fan of the public ugly cry — in front of Oprah, no less! — but we were all in it together. And it was okay.

“The call isn’t something outside of you, ever,” Oprah told the “conversation” audience aboard the ship. “Everybody has it, and you have until the last breath to fulfill it. To contribute to this amazing planet we live on. What an incredibly amazing thing that you get to be you.”

Related note: If the call ever comes to take a cruise with Oprah, answer.

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