As the world seems to crash and burn around us, millennials often long for simpler times when the most pressing issues were finding the perfect low-rise jean or picking the most eye-catching AOL screen name. Y2K (the year 2000) also ushered in a whole new generation of beloved celebrities who influenced our entertainment and style choices. And though we often look back in disgust at our skinny eyebrows and obsession with glitter, there is no denying that these temporary bouts of nostalgia make us feel all warm and fuzzy inside.
But that feeling doesn’t have to fall by the wayside and into the pits of obscurity forever. So, we decided to pair a handful of our favorite Y2K celebrities with boutique hotels that capture the A-listers’ unique brands and personalities. Sure, many of these comparisons may be reaches, but it’s time we had a little fun with travel again by using our biggest childhood influences to make informed adult decisions, like booking high-quality accommodations.
Alcazar Hotel (Palm Springs, CA): Jennifer Lopez
Let’s get loud. There is no denying that Jennifer Lopez is a fashion icon, and arguably, her most famous look yet was the palm-adorned Versace gown from the 2000 Oscars. With palm in its name, a trip to Palm Springs can channel these chic desert vibes, especially at Hotel Alcazar, where the tall grass (not tree!) runs rampant around the property’s iconic pool and bustling courtyard. It’s a must-visit for anyone in need of a warm-weather escape.
Windjammer Landing Resort & Residences (Saint Lucia): Destiny’s Child
Windjammer Landing Resort in St Lucia debuted three-story beachside villas, complete with all the bells and whistles you’d come to expect at a luxury property in the Caribbean. And since the best things apparently come in threes (levels, in this case), we couldn’t help but sing the resort’s praises, much like famous R&B trio Destiny’s Child. Beyoncé would obviously get the primary suite to herself, but rooms are grandiose and designed to host entire families (or girl groups) and without the worry of bills, bills, bills back at home. Best of all? Each home away from home is equipped with a private rooftop pool that offers panoramic views of the resort and ocean.
SB Winemaker’s House and Spa Suites (Mendoza, Argentina): *NSYNC
While the resort boasts only a handful of suites, they harmonize flawlessly, much like a boy band, on the tree-filled property that sits adjacent to the Andes. Say bye, bye, bye to travel aches and pains upon arrival, as the property’s rooms are also fitted with oversized concrete tubs, as well as a dry sauna, steam room, and sensations shower that complement a robust menu of in-room treatments.
Tabacón Thermal Resort & Spa (Arenal, Costa Rica): Christina Aguilera
Get “dirty” during a hike up famed Arenal volcano before enjoying the fruits of your labor in one of Tabacón’s 20-plus thermal pools. Each dip is different from the next, much like Christina Aguilera’s diverse catalogue of albums, but you’ll ultimately find one that tickles your fancy and allows you to breathe, decompress, and enjoy the sights and sounds of Costa Rica’s thriving wildlife. Spacious rooms also offer unobstructed views of the region’s tropical landscape, including trees that contain birds, camouflaged insects, and even sloths.
Alexander’s Guesthouse (Key West, FL): Britney Spears
Embrace your inner Britney with a naked twirl around your living space (and the property!) at clothing-optional Alexander’s Guesthouse in Key West. The boutique hotel is also LGBTQ+-friendly to accommodate those who likely stan our pop princess and often find themselves in need of some island paradise (much like Ms. Spears herself, who can often be found on the beach or near a pool on Instagram). After one stay, you’ll inevitably “oops” and return again and again.
Calilo (Ios, Greece): Missy Elliott
Eclectic, eccentric, sometimes misunderstood, but full of heart, Calilo embodies the artistry of legendary Missy Elliott. This one-of-a-kind architectural masterpiece sits pretty on the secluded island of Ios with cascading suites, towering waterfalls, stone mosaics, and hand-painted sculptures that rival that of the late and great Keith Haring. And while its abundance of inspirational messages can often read as gimmicky and over-the-top, they ultimately inspire when set among a backdrop of this level of beauty and grandeur.
