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Shailene Woodley

Joelle Mentis, Writer

Shailene Woodley

When your movies make over one billion dollars, it puts you in a special class of achievement. It also means that you’ve traveled to a place or two to film a movie, attend a premiere, and take some well-deserved time off. So we’ll go where Shailene Woodley is headed. Here are a few of her favorite spots.

Shailene is pretty amazing. But those billions in box-office receipts also came from some great teamwork. An actor needs to have good relationships in order to thrive. And Shailene prioritizes those, especially when she’s on set. Traveling with her co-stars is often a bonding experience for her. In 2013, on the set of The Spectacular Now, Shailene met her future best friend and vacation partner, Miles Teller. Miles is arguably just as famous and talented as Shailene. And the two had similar tracks, together going on to star in the Divergent series and in The Fault in Our Stars. Here are some of their favorite locales.

Maui Vibes

For a sweet couples’ vacation in Maui, Shailene and then-boyfriend Aaron Rodgers, as well as Miles and model-wife Keleigh Teller (nee Sperry), spent time hiking to waterfalls and enjoying beachside dinners. Instead of doing big resort-y things, they opted to steer their trip toward the hidden natural features of Hawaii with the help of a local guide. A key benefit of that? Finding ponds with prime cliff-jumping.

In Maui, it wasn’t a surprise that Shailene spent most of her time on foot. If we were to guess where she hiked, we would think Pipiwai Trail for the waterfalls. Located above the Seven Sacred Pools, Pipiwai is a four-mile loop with multiple waterfalls for swimming. One even has a 400-foot drop. The views provide the picture-perfect Hawaii experience and made really great backdrops for her Instagram. Because the couples loved traveling together so much, they dubbed themselves the “soulmate squad.”

Recently, COVID-19 drew attention to the lack of sustainability of some tourism in Hawaii. We’re guessing Shai thought about that by using local guides and leaving no trace where she visited. Beyond her travels, Shailene opts for the natural side as well, adhering to an inspired regimen of plant-based products for her diet, skin, and clothing. We’d also bet she’d stay at Sensei, a resort promoting sustainability. Inspired by a prominent ex-physician and scientist, Sensei wants guests to learn and live by the best lifestyle practices possible for long-term wellbeing.

Kentucky Derby Dreams

The soulmate squad also got “Down and Derby” at the famed Kentucky horse race, thoroughly enjoying the classic Churchill Downs event (which Rodgers frequently attends). Some people think that the Derby is the best sporting experience there is. Not only do guests watch horses race around a track. But they also share in the pomp and circumstance of it all. The Kentucky Derby draws over 150,000 guests. And they’re not just sitting and cheering. They’re wandering, drinking, and showing off their impeccable, if impractical outfits. Shailene and friends were part of it all — from stopping by to see the track up close to finding the perfectly poured mint julep. Typically, Shailene isn’t one to obsess over fashion — let alone hats — but she gladly lived up to the hype in a hot pink suit and large, white wide-brimmed hat. Her companions were also dressed to the nines.

While Shailene and Miles have the kind of friendship that’s never-ending and makes vacations much more exciting, Shai’s on-again off-again relationship with Rodgers is now off. She recently broke her engagement with the pro footballer. Despite the tumult since their travels, the strong run of couples’ trips should inspire all adventurous couples out there.

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