First Stop: Palm Springs
First stop, right after the Inauguration? The sunny climes of Palm Springs, California, where the Obamas stayed in an 11,000-square-foot mansion owned by White House interior designer Michael Smith and his partner, former U.S. Ambassador to Spain and Andorra, James Costos. Supremely private, it’s perched well above the majestic Coachella Valley—the same view (as Smith pointed out to Architectural Digest) that JFK woke up to 50 years ago when he stayed at Bing Crosby’s house Despite the cloudy skies, Barack got in a few rounds of golf in at Porcupine Creek, Larry Ellison’s private course.
How to follow suit: If you’re not friends with Smith, check into the historic La Quinta Resort nearby Under the Waldorf Astoria umbrella, it’s as ritzy as they come, and has hundreds of acres of golf courses to call its own.
Stop 2: British Virgin Islands
Just a few days later, the former FLOTUS and POTUS hopped on Sir Richard Branson’s private jet and flew to Necker Island, the billionaire’s private island in the BVIs. The 74-acre resort is almost as exclusive an accommodation as the Lincoln Bedroom: You have to rent out the whole thing, but it comes with meals and booze, a staff of 100, tennis courts, spa treatments, Pilates classes, a DJ, and room for 34 of your closest friends. Branson challenged Obama to learn to kitesurf—a sport that the Secret Service had nixed during the president’s term—thus setting up the best photo op of the year.
How to follow suit: If you don’t want to buy out the entire island, we have good news. Each year Necker Island has “Celebration Weeks”—periods where you can book a single room for a set 7-day period. This year’s window will be in September, every week, Saturday to Saturday.
Stop 3: French Polynesia
In March, the Obamas flew to yet another private island, this time in the South Pacific. The Brando, the former retreat of the Godfather himself, is now a secluded eco-luxe resort—powered by solar energy and coconut oil—with stunning white-sand beaches, coral reefs and a turtle sanctuary. Barry and Michelle stayed for a full month to begin work on their memoirs, but managed to find time for a little paddleboarding (no kitesurfing, though!) and even a jaunt on David Geffen’s $300 million yacht, which was moored off the coast of neighboring Moorea. Who tagged along? Oh, just Oprah, Tom Hanks, and Bruce Springsteen.
How to follow suit: We can help you with The Brando, but you’re on your own with Geffen’s yacht.
Stop 4: Tuscany
May saw President and Melania Trump heading to the G-7 summit in Sicily…. and the Obamas on a six-day romp through Tuscany (rub it in a little?). Staying at Borgo Finocchieto, a gorgeously restored century villa near Montalcino owned by John Phillips, Obama’s ambassador to Rome. The former president played a round at Castiglion del Bosco (an exclusive 18-hole golf course, open only for its Golf Members and hotel guests..and special occasions like a visit from the former president and first lady), the Ferragamo family’s golf club in the Val d’Orcia, and to top it off, he and the former first lady biked the Italian hillsides and strolled around Siena.
Stop 4: Tuscany The five houses at Borgo Finocchieto sleep 44 and must be rented as a group. If your entourage isn’t quite as large, check into the Rosewood Castiglion del Bosco, part of Ferragamo complex, and schedule a tee time.
Stop 5: Indonesia
With summer vacation in full swing, it’s time for family vacation. In June, according to the Jakarta Post, the entire Obama clan visited Barack’s boyhood home, making stops in Bali and Java. This wasn’t just about beach time: They paid a visit to Ubud’s Agung Rai Museum of Art, saw the famed Jatiluwih rice terraces and went rafting on the Ayung River. After wrapping up Bali, they flew to Yogyakarta, the cultural hub of Java, where Obama’s mother moved with him at the age of six.
How to follow suit: It's rumored that the Obamas stayed at the Four Seasons Resort Bali at Sayan, reach out to one of our agents and we'll customize your own Indonesian adventure.