You know owner Mark Christy as the owner of Hobie, the ubiquitous maker of sailboats and surfboards. Now the Laguna Beach, Calif., native is adding a feather to his cap with the opening of his first hotel, the Ranch Laguna Beach. It’s the first addition to the local hotel scene in over a decade, set on 83 acres of canyons and coast. Inside, the vibe is more upscale cottage than surfer cool, with batten wood-clad walls, distressed leather chairs, and rope-suspended, wrought-iron lanterns. Bonus: There’s extensive programming for all ages, including a Ranger Station kids' camp, yoga, archery, whale watching, and plein air painting classes. From $479.


Oil Nut Bay
Virgin Gorda, British Virgin Islands

It’s only accessible by helicopter, but this exclusive gem in the British Virgin Islands is worth the journey. It’s part of the “Billionaire’s Playground,” a nicknamed chain of islets that are mostly private-owned (by the likes of Richard Branson and Larry Page). Here, 88 villas, some forming a resort and others available for ownership, are spread on a parcel of 300 pristine acres; guests have access to such activities as deep-sea fishing, snorkeling, sailing, and pickleball—an increasingly popular spin on tennis. From $750.


Faena Miami Beach
Miami

There isn’t always substance behind the glitz and glam of Miami Beach, but that’s not the case at Faena, a new hotel and cultural complex by the namesake Argentine developer. It’s home to some of the most whimsical décor this side of the Atlantic, including sumptuous custom fabrics on nearly every surface, a mural-covered space that’s literally called “the Cathedral,” and “Gone But Not Forgotten,” a gilded wooly mammoth by Damien Hirst that guards the pool deck. The food cred doesn’t hurt, either—after a months-long pop up of Chicago’s Alinea, the first floor now contains the country’s first restaurant by South American grill master Francis Mallman; upstairs, there’s a spot by Austin darling Paul Qui. From $381.


The Asbury
Asbury Park, N.J.

Luxury on the Jersey Shore? In a former Salvation Army building, no less? Believe it. Thanks to a multibillion-dollar renovation, Asbury Park has its first upscale hotel, making the long-forgotten destination a viable alternative to weekends out East. Among the retro-inspired draws: a rooftop movie theater meant to resemble an old-school drive-in, a rec room with pinball machines, and direct access to the completely reimagined boardwalk, whose summer musical lineup includes such names as the Lumineers and the Violent Femmes. From $95.


Four Seasons Lanai
Lanai, Hawaii

This iconic resort, known as the spot where Derek Jeter golfs and Bill Gates proposed, has been given a stem-to-stern overhaul by its new owner, tech billionaire Larry Ellison. Now rooms all face the ocean for postcard-worthy views, and the dated interiors have been swapped for a kitsch-free Hawaiian aesthetic. (Think thatched wallpaper, sculptural rattan chairs, and bamboo-clad bathrooms.) If it meets Ellison’s exacting standards—and after a $450 million investment, it does—it’ll certainly meet yours. From $1,075.


Tcherassi Hotel + Spa
Cartagena, Colombia