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Where President Obama Vacations

Joelle Mentis, Writer

We’ve gotta give it to Michelle and Barack — these two just know how to live. Their travel destinations are what #goals are made of. They vacation with Oprah and Tom Hanks in French Polynesia, and take Tuscany on in their own private Italian village. But Hawaii, our former president’s home state, is extra-special to the family. This is really where President Obama vacations.

The Accommodations: Paradise Point Estates


This luxury rental is nicknamed the “Winter White House” for a reason. While the couple and their daughters were in the White House, they made it a tradition to cap off a presidential year with a tropical getaway to this estate.  This is really where President Obama vacations and decompresses with his family. The five-bedroom, five-and-a-half-bath home with a lagoon and hot tub spa is the designated recharge spot for the fam.  Its location is prime in gorgeous Kailua on the island of Oahu, with its world-class beaches, golfing and dining.

Only 25 minutes from where President Obama grew up, the home is rented for just under $5,000 a night. The estate blends seamless indoor and outdoor living. The home centers around an incredible lagoon-style pool ensconced by tropical waterfalls and native vegetation. Paradise Point Estates is the perfect place for a romantic getaway and is secluded enough for someone as high profile as President Obama.

The Restaurant: Ya-Ya’s Chophouse

The Obamas are always down for something upscale and cool, and Ya-Ya’s is just that. The steakhouse and seafood restaurant has all the classics. They have massive seafood towers and filet mignon, seared salmon and prime cuts of Wagyu.  This is not a stuffy steakhouse though.  The vibe is distinctly modern — low lit with music bumping in the background.

The couple and Barack’s sister came to the restaurant dressed in jeans. While it’s  a departure from their usual professional look, it matched the casual, unfussy ambiance of the evening. After all, this is where President Obama vacations, so he’s off-duty by definition. But that doesn’t mean they didn’t dish out the big bucks, as the restaurant charges a premium for the best cuts. Highlights on the menu are the king crab and the porterhouse.

The Hangout: Nu’uanu Pali

When in Hawaii, one of Obama’s favorite activities is golf.  He frequently hits the courses at the Mid-Pacific Country Club and Marine Corps Base.  But when the fam really needs to relax, they head to their favorite lookout spot — Nu’uanu Pali. Nu’uanu Pali offers cliff-top panoramic views of the surrounding Oahu coastline.

From the perch thousands of feet above sea level amid steamy Hawaiian clouds, you can view famous landmarks and historical battle sites. The view from the mountain’s peak is a site to behold.   From here there are seemingly endless miles of open ocean speckled with nearby islands.  It’s the iconic and picturesque and quintessential Hawaiian landscape. At just $3 for parking, the summit is an affordable way to spend an afternoon.  There’s no question why this is where President Obama vacations and really unplugs.

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