5 Girlboss-Approved Getaways for the Holidays ✈️
We’re not saying we’ve already mentally clocked out for the holidays, but we’re also not not saying that. 🤪 In between Q4 deadlines and back-to-back meetings, the Girlboss team has been scheming up our dream holiday escapes. So, why not take a break and plan yours?
Here are five Hilton stays we’d book in a heartbeat, from a Caribbean beach trip with a chihuahua and a wine-soaked weekend in Napa to a Manhattan Christmas straight out of a movie, a dreamy Hawaiian escape, and a ski getaway with Dad.
Pick your favorite, then go ask for the days off.
Oh, and why should you book with Hilton? Guests can earn Hilton Honors Points on eligible stays, access member-exclusive pricing, use Points & Money redemptions, and enjoy the benefits associated with their Hilton Honors status. Sounds like a no-brainer to us.
Waldorf Astoria Riviera Maya, an All-Inclusive Experience
📍 Cancún, Quintana Roo
“I’ve always dreamed of taking a trip with my chihuahua, Romeo, which is why my pick is the pet-friendly Waldorf Astoria Riviera Maya. Travelling with him has always felt too complicated, but having a personal concierge to handle the details would give me real peace of mind. He’d be spoiled with treats, a cozy bed, and his own in-room dining menu.
The resort sits on 100 acres of private coastline and mangroves, the perfect backdrop for morning yoga by the sea. I’d spend my days in the resort’s swim-up pool or snorkelling in the Caribbean. In between swims, I’d be grabbing chilaquiles at Chaya or tacos at JA’O. For a bit of adventure, I’d head to Tulum’s archaeological site, then cool off in one of the region’s cenotes. And every evening, I’d unwind by watching the sunset to live music, with Romeo curled up next to me.”
— Vanessa, Managing Director
“As a wine lover, the Casa Mani Resort Napa Valley, Curio Collection by Hilton is at the top of my list, and you don’t even need to drive anywhere to take advantage of all the things Wine Country has to offer. I’d start my mornings by walking to First Street’s tasting rooms, then spend my afternoons doing wine tastings in the resort lobby. After a day of sipping, I'd unwind with a spa circuit or a dip in the outdoor pool and hot tub. Plus, there are wine fridges in every room and patios with private fire pits. Cheers to that.”
— Janelle, Brand Partnerships Manager
New York Hilton Midtown
📍 New York City, NY
“As a lifelong fan of Home Alone 2: Lost in New York, I’ve dreamt about spending the holidays at a cushy hotel in NYC for as long as I can remember. Considering that the New York Hilton Midtown is in the heart of Manhattan and just a three-minute (!!) walk to the iconic Christmas tree at Rockefeller Center, I can’t think of a better hotel to live out my Christmas in New York dreams. And yes, I plan on ordering a glorious room service sundae complete with all the fixings!”
— Lara, Contributing Writer
“Hawai'i has been on my dream destination list for years! So my pick would be The Ambassador Hotel of Waikiki, Tapestry Collection by Hilton. I'd love a getaway with plenty of beach time and the chance to learn more about Native Hawaiian history and traditions!
My perfect day would start with a sunrise hike, followed by breakfast and some relaxation time by the ocean. Then I'd join a lei-making class led by a cultural practitioner to understand the meaning behind the craft, stop for some yummy poke, and spend the evening enjoying Hawaiian music and hula!”
— Cheska, Social Media Editor
Canopy by Hilton Deer Valley
📍 Park City, UT
“My favorite memories of wintertime are skiing with my dad, but where I’m from isn’t known for world-class slopes (sorry, Ontario, Canada!). So my dream trip would be a ski getaway at Canopy by Hilton Deer Valley in Park City. It’s a powder hound’s paradise because the gondola is right out the front door, and the ski valet and heated boot storage mean my gear stays nice and toasty.
After a day on the hill, I’d soak my sore legs in the steam room and head up to Alpine Attic for a mocktail with gorgeous mountain views. Then I’d finish the night with a big bowl of cavatelli al pestoa at Tavolona (my gluten and dairy intolerance doesn’t exist in this fantasy world). Plus, the trip wouldn’t be complete without a stroll down Historic Main Street, all lit up for the holidays. And forcing my dad to snap some pictures for IG. 🤪”
— Victoria, Executive Editor
There’s a Hilton for whatever kind of break you need this holiday season. Guests who book directly through Hilton can earn Hilton Honors Points on eligible stays, access member-exclusive pricing, use Points & Money redemptions, and enjoy the benefits associated with their Hilton Honors status.
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