The spring break week initially began with Trump's three eldest children and their families, including Donald Jr. and Vanessa Trump and their five children, Ivanka Trump and Jared Kushner and their three children, and Eric and Lara Trump, who announced earlier this week they are expecting their first child in September, and also brought along their two dogs.
Not present: the President himself, the first lady, Tiffany Trump or Barron Trump.
The President's signature 757, dubbed "Trump Force One," was the transportation of choice for the trip. Donald Trump Jr. posted a shaky video from the cockpit as the plane took off from New York.
But after a safe landing, an accident unexpectedly ended the trip for Donald Jr.'s family: son Tristan, 5, broke his leg shortly after arrival.
"For those who don't know Vanessa and I had to cut our vacation short (from 5 days to about 12 hours... ugh😭) because our other little man Tristan fell and broke his leg pretty badly," Trump Jr. posted on Instagram.
The President's eldest son, his wife, and four of their five children returned to New York; son Donnie, 8, stuck around with his cousins, aunts and uncles.
The remaining Trump siblings and spouses have taken advantage of the Aspen amenities, Ivanka posting a photo of her "exhausted little skiers" Arabella and Joseph, Lara posting "awesome views" from a morning hike with Eric and his brother, and paparazzi snapping the family skiing and grabbing ice cream cones.
It's unclear how much the vacation is costing taxpayers, as the family travels with a bevy of Secret Service agents -- some of whom even accompanied their protectees on the ski slopes. The Aspen Times reported
that the Secret Service "signed a contract last week for more than $12,000 with the Aspen Valley Ski and Snowboard Club for rental ski equipment and clothing."
CNN was unable to independently verify that number through the Federal Procurement Data System
The Trumps weren't exactly met with open arms during this visit to Aspen, situated in Pitkin County where just 24% of residents voted for Trump in the 2016 election.
The Pitkin County Commissioners reportedly took out a full-page ad in both the Aspen Daily News and the Aspen Times
welcoming the family and urging climate action. Vanity Fair reported "annoyed" New York moms
and limited availability at local dining hot spots. And "dozens" of protesters took to the town's Main Street on Sunday morning, per the Denver Post
The family has a long and storied history with Aspen.
Ivana Trump, the President's first wife and mother to his three eldest children, was a competitive skier in Czech Republic, and her children grew up skiing, often traveling to the Colorado ski town. Donald Trump Jr. even lived there for a year after college.
Aspen was the site of a very public feud between the future President, Ivana, and Marla Maples, who later became Trump's second wife.
When the family was vacationing there in December 1989, Ivana, approached Maples at a popular mid-mountain restaurant and told her to stay away from her husband.
"She couldn't pronounce my name, but she was asking me if I was Moola or whatever . . . and she just asked if I was the one who had been loving her husband for years. . . . I didn't want to scream," Maples told Vanity Fair's Maureen Orth
in a November 1990 profile. "It was obvious she wasn't happy."
Per Orth, Donald Trump told Maples to leave, and the then-husband-and-wife continued their fight on the ski slopes.
But more than 26 years later, the Aspen tradition continues.
"It's our tradition to do a ski trip together once a year. My mother was a competitive skier, and we grew up on the slopes. I love seeing all of the cousins playing together in the snow. We've made a lot of great memories out there and I am excited to keep the tradition going," Ivanka Trump wrote in a 2015 blog post
for her namesake apparel and accessories brand, sharing family photos from trips past.