Get a prime view of one of Oprah's favorite things. Photo courtesy of Ladera resort.

Ladera Resort, St. Lucia
Oprah named the Piton mountains of St. Lucia one of the five places to see in your lifetime. And perhaps the best view of the natural wonders comes courtesy of eco-chic Ladera resort, featuring open-wall rooms built into the hillside directly overlooking the prime scenery. The rustic, luxury treehouse feel may be a big change from stars' usual accommodations, but that didn't stop Oprah, Bill Gates, David Bowie, and Matt Damon from taking in the view at the resort. The ultra-private rooms even feature their own plunge pools, so there's barely any reason for stars to leave their hillside enclaves.
What to wear: An old bathing suit (to enjoy the nearby sulfur springs like Jake and Vienna on "The Bachelor") and a Rachel Pally maxi dress for dinners al fresco.

Gansevoort Turks and Caicos
The Gansevoort Hotel in New York City is known for attracting a stylish crowd. Those seeking the same amenities in a sunnier location can now visit its Caribbean sister hotel in Turks and Caicos. The luxe resort caters perfectly to fashionistas (the staff's uniforms are designed by Rag & Bone), beauty buffs (thanks to the full-service Exhale Spa), and the celeb set (Ellen Pompeo, Molly Sims, Ashley Greene, Rashida Jones, and Emmanuelle Chriqui have all been guests).
What to wear: Ikat bikini by Tibi -- this resort is trendy, trendy, trendy.

The Oberoi Rajvilas, Jaipur
When stars like Brad Pitt, Madonna, Julia Roberts, and Naomi Campbell visit India, they head straight for the country's most lush and opulent luxury hotels (lucky them). They've all stayed at the stunning Oberoi resort in Jaipur, which features your choice of well-appointed rooms, "luxury tents," or villas with private pools. The spa offers both Ayurvedic and western treatments, and models some of its pampering packages after royal Rajasthani traditions.
What to wear: A white eyelet dress and big floppy hat to block out the sun in style.

Villa Aquamare, Virgin Gorda
This super-exclusive resort may only be a few years old, but it's already hosted Hollywood bigwigs like Rihanna and Harisson Ford & Calista Flockhart. The draw? Villa Aquamare consists of only three 8,000 sf villas on a private beach enclave, so it feels like you're the only ones on the island. Take that, papparazzi! www.villaaquamare.com
What to wear: Sunglasses. Havaianas gladiator sandals. Whatever else you do (or don't!) wear is up to you at this super-private villa.