23 Extravagant Celebrity Winter Vacations to Drool Over This Season

by Jason Pham
Dec 15, 2017 at 5:00 p.m. ET

When you think of your ideal vacation spot, it’s easy for your mind to go to warm tropical beaches in the dead of summer. And though there’s nothing wrong with lounging on a beach with a piña colada-filled pineapple in hand (we dream about it pretty much every day), we’re here to make the case for winter vacations.

Long gone are the days when we need to wait until summer to pack our suitcases and jet off to some extravagant getaway. Fun is year-round, so we might as well take advantage of that winter holiday time to travel the world — or, you know, the most Instagram-appropriate spots. Don’t believe us? Maybe the Instagrams of stars like Kourtney Kardashian, Victoria Beckham and Bella Hadid will convince you.

Scroll through any A-lister’s Instagram feed in the winter, and you’ll likely see albums of shots at some luxurious getaway. Whether it’s a sandy beach or a snowy wonderland, Hollywood knows how to vacation and a little cold isn’t going to stop them. To inspire your own winter vacation, we rounded up 23 drool-worthy celebrity getaway spots to fly to this holiday. See them ahead, and who knows? Maybe you’ll be buying plane tickets in the near future.


Originally posted on StyleCaster

1 /23: Kourtney Kardashian — Aspen, Colorado

1/23 :Kourtney Kardashian — Aspen, Colorado

In January 2017, Kourtney Kardashian, her ex, Scott Disick, and their three kids, Mason, Penelope and Reign, spent New Year's in Aspen, where they hit the slopes, played in the snow and spent tons of cozy nights in a fireplace-heated cabin. Even a vacation with her ex isn't stopping Kourtney from soaking in Aspen's gorgeous snow-blanketed views, as seen in this Instagram selfie.

2 /23: Nicki Minaj — Turks & Caicos

2/23 :Nicki Minaj — Turks & Caicos

To savor the last days of 2016, Nicki Minaj traveled to Turks and Caicos, where she served major looks in several jaw-dropping one-piece swimsuits. The rapper, who also celebrated her 34th at the tropical location, spent the trip, as expected, taking a slew of slayworthy Instagram selfies in studded swimsuits and heels. (Who says you can't wear heels on the beach?)

3 /23: Chrissy Teigen — St. Barts

3/23 :Chrissy Teigen — St. Barts

For Chrissy Teigen and John Legend's daughter Luna's first family vacation, the A-list couple took her to St. Barts in the West Indies. On the trip, the celebrity family did tons of kid-friendly activities, like sightseeing, swimming in shallow waters and taking selfies against gorgeous seaside backdrops. 

4 /23: Karlie Kloss — Sydney, Australia

4/23 :Karlie Kloss — Sydney, Australia

In December 2016, Karlie Kloss flew across the world to Sydney, Australia, to soak in the sun at the city's picturesque Tamarama Beach. There, Kloss posed for a selfie next to crashing waves, rode a double-decker buspaddleboarded and visited Bondi Beach like the true tourist she is.

5 /23: Taylor Hill — Grand Lake, Colorado

5/23 :Taylor Hill — Grand Lake, Colorado

For 2016's winter holiday, Taylor Hill returned to her home state of Colorado and ventured a few hours out from her hometown in Arvada to Grand Lake, a picturesque lakeside town with Instagram-worthy views of snowy hills and frozen ponds. Clearly, Hill took the opportunity to post her own 'gram in which she posed in front of snow-covered mountains while dressed in a snuggly scarf. Hill's vacay also shows you can still have a fun-filled winter trip without breaking the bank and venturing too far from home.

6 /23: Gabrielle Union — Miami, Florida

6/23 :Gabrielle Union — Miami, Florida

In December 2016, Gabrielle Union and her husband, Dwyane Wade, traveled to Miami, Florida, to celebrate the holidays. There, the couple lounged on yachts (while sporting killer sun visors, we might add), explored the city's sights and explored the city's beachside sights.

7 /23: Madonna — Switzerland

7/23 :Madonna — Switzerland

In winter 2016, Madonna and four of her children, Lourdes, Rocco, David and Mercy, traveled to Switzerland for a snowy family getaway. There, the family, along with Madonna's family friend, David Blaine, hit the slopes on the Swiss Alps, soaked in gorgeous snow-covered views and took tons of goofy selfies, proving that going on vacation with your mom (especially if she's Madonna) doesn't have to be a bore.

8 /23: Hilary Duff — Hawaii

8/23 :Hilary Duff — Hawaii

In January 2017, Hilary Duff and her son, Luca Cruz, rang in the new year with a trip to Hawaii. Though Duff didn't reveal the exact city she went to, her Instagram gave us plenty to ogle — including a mouthwatering colorful snow cone, plenty of bikini selfies and an epic shot of her sitting next to a Hawaii mural. Duff's Hawaii trip was only a few days after she and Luca left a snowy wonderland, so talk about a climate shift.

9 /23: Ashley Graham — San Juan, Puerto Rico

9/23 :Ashley Graham — San Juan, Puerto Rico

Before the end of the year, Ashley Graham and some girlfriends flew to San Juan, Puerto Rico, where judging from her social media, things got pretty lit. Not only did Graham soak in the city's beautiful architecture, but she also shared an epic video of her twerking on a beach. Ashley, invite us on your next vacay, will ya?

10 /23: Shay Mitchell — Maldives

10/23 :Shay Mitchell — Maldives

It might still be a few days from December, but Shay Mitchell is starting her winter vacation early. Recently, the actor traveled to the Maldives islands in South Asia, where she took tons of palm tree picturesate bananas, posed nude and drank coconut juice straight from a coconut. (It's the only way to do it.)

11 /23: Sara Sampaio — Lima, Peru

11/23 :Sara Sampaio — Lima, Peru

Victoria's Secret model Sara Sampaio rang in 2017 with a trip to Lima, Peru, where she and fellow model, Daniela Lopez Osorio, soaked in the gorgeous sights, as seen in this Instagram pic of the duo happily posing on a road separating the beach from the city.

12 /23: Chloë Grace Moretz — Telluride, Colorado

12/23 :Chloë Grace Moretz — Telluride, Colorado

Chloë Grace Moretz and her brother, Brandon, braved the cold in Telluride, Colorado, where they rode horses in the snow, for a trip in January 2017. Though the subzero temperatures probably weren't the most fun, Moretz did end up with this badass selfie of the duo looking extra cool mounting two steeds.

13 /23: Hailee Steinfeld — Nassau, Bahamas

13/23 :Hailee Steinfeld — Nassau, Bahamas

To celebrate the last few days of 2016, Hailee Steinfeld and her rumored boyfriend at the time, Cameron Smoller, traveled to Nassau, Bahamas, where they escaped the cold weather for warm sandy beaches, huge palm trees and beautiful sunsets.

14 /23: Josephine Skriver — Manarola, Italy

14/23 :Josephine Skriver — Manarola, Italy

Victoria's Secret model Josephine Skriver traveled to Manarola, a town in Cinque Terre, Italy, for a winter getaway in winter 2017. Though the location wasn't as warm as it is in the summer months, judging from Skriver's cozy attire, its sights were just as breathtaking.

15 /23: Halle Berry — Malibu, California

15/23 :Halle Berry — Malibu, California

Halle Berry didn't venture far from her Los Angeles home when she spent a staycation in Malibu, California in late 2016. The actor celebrated Christmas with a movie-moment run on the beach with her hair flowing in the wind against a gorgeous California ocean backdrop.

16 /23: Jourdan Dunn — Barbados

16/23 :Jourdan Dunn — Barbados

Jourdan Dunn traveled to Barbados in the Carribean to warm up in winter 2016. The vacation, which took place around the holidays, included drinking coconut juice straight from the source while soaking in the island's gorgeous green-blue seas.

17 /23: Bella Hadid — Aspen, Colorado

17/23 :Bella Hadid — Aspen, Colorado

For New Year's 2017, Bella Hadid, her sister, Gigi, and her mom, Yolanda, traveled to Aspen to spend a snow-filled vacation skiing, playing with adorable sled dog puppies and cozying up next to giant bonfires. It's a winter vacation straight out of Game of Thrones, minus, you know, subzero temperatures and giant ice monsters.

18 /23: Chanel Iman — Sydney, Australia

18/23 :Chanel Iman — Sydney, Australia

Like her fellow supermodel, Karlie Kloss, Chanel Iman also traveled across the world to Sydney, Australia, to spend the winter holidays in 2016. Though she didn't take as many pics as Kloss, Iman did share one stunning shot of herself walking down a beach with crashing waves and giant rocks behind her. Her caption, "Holiday Summer," speaks volumes about how you can spend your summer vacay in the winter.

19 /23: Kaia Gerber — Miami, Florida

19/23 :Kaia Gerber — Miami, Florida

Kaia Gerber and her family — mom Cindy Crawford, dad Rande Gerber, and brother, Presley Gerber — spent the last month of 2016 vacationing in Miami, Florida, where they soaked up the sun, frolicked in swimsuits and posed for beach selfies. Kaia even celebrated 1 million Instagram followers at the coast-side city, so you know that trip was good.

20 /23: Kate Hudson — Aspen, Colorado

20/23 :Kate Hudson — Aspen, Colorado

Kate Hudson, her mom, Goldie Hawn, her friend, Dakota Johnson, and Johnson's mom, Melanie Griffith, spent winter 2015 in Aspen for a Hollywood family gathering. There, the foursome cozied up in a cabin and even tried drunk skiing. (Spoiler alert: It ended up with them lying on their backs in the snow, though we're sure they had a good time.) Aspen seemed to be such a popular spot that Hudson returned the next year, though she was able to stand on her skis that time.

21 /23: Bella Thorne — Bahamas

21/23 :Bella Thorne — Bahamas

Bella Thorne rang in the new year with a trip to the Bahamas with a few girlfriends, where the actor did a ton of fun-filled activities — like pet a shark and sightsee with a Polaroid camera — with her sister, Dani, and several Famous in Love costars.

22 /23: Victoria Beckham — Maldives

22/23 :Victoria Beckham — Maldives

For New Year's 2017, Victoria Beckham, her husband, David, and their four kids, Harper, Brooklyn, Cruz and Romeo, traveled to the Maldives in South Asia, where they rang in 2017 with a selfie by a Christmas tree on the beach. On the vacation, Harper left her mark by expresing her love for her A-list parents in sand writing.

23 /23: Reese Witherspoon

23/23 :Reese Witherspoon

Though Reese Witherspoon didn't reveal where she spent her winter 2016 vacation, she did provide tons of photos to drool over. During the trip, the actor and her kids spent time drawing hearts in the sand, riding inflatable flamingos and watching stunning orange and purple sunsets