Matt Roloff is enjoying some fun in the sun while in Hawaii, spending time with his girlfriend, Caryn Chandler, son Zach Roloff, Zach’s wife Tori Roloff and grandson Jackson. The Little People, Big World star shared several photos from the vacation on his Instagram page, which provided a venue for fans to worry about Jackson’s safety.
One photo shared on Wednesday showed the family foursome kayaking with a beautiful Hawaii background, while Jackson sat in Tori’s lap in the photo. The post also included a second photo of Jackson adorably standing in the kayak.
Videos by PopCulture.com
“Sailing the high seas off the coast of Maui,” Roloff wrote in the caption.
The post was met with some fans complementing Jackson on his cuteness, but others blasted Roloff for not wearing a lifejacket.
“No life vests for anyone, what if the damn thing [tips] over?” one Instagram user asked.
“Hope Jackson has a life jacket,” added another.
“No life jackets? It looks like a lot of fun,” added another fan.
Of course, Jackson was fine and appeared happy in other photos from the trip. On Friday, Roloff shared two more photos of his day with his grandson in Maui, including one with Jackson on his lap.
“Such an amazing day with my grandson Jackson and [Chandler] Zach and [Tori] explored the road to Hana while we got the best end of the deal. A full day with the little fella. Thanks [Four Seasons Maui] for being so incredible,” Roloff wrote.
Tori has also shared photos from the Maui trip, including an adorable photo of herself with Zach and Jackson on the beach together. “Maui is great. But my paradise is these two boys,” she wrote.
Tori also shared updates with fans, confirming he is already walking and loves the family dog Murphy.
“I have lost count of how many teeth he has and he uses them any chance he gets to chow down on some grub. He’s obsessed with mule rides at the farm and gets so excited when he sees grandma/grandpa patton/Roloff,” she continued. “The past year and a half has been the best time of my 27 years of life and I can’t wait to see what else God has in store. Happy half birthday little man. Mama and dada and Murphy love you so much.”
Jackson, who celebrated his first birthday in May, often appears in photos with his grandparents and they often get comments from fans nervous about his safety. Tori has become so used to it that she has preemptively responded to mommy shamers before they even get a chance to criticize her.
“Before I get ripped apart in the comments please take into consideration my husband and I would never put baby j in harms way. K thanks enjoy,” Tori wrote in July when she shared a photo of Jackson sitting on a tractor with Zach.
Photo credit: Instagram/Matt Roloff
More Reality
-
Photo by Fred Hayes/Disney via Getty Images -
Photo by Getty Images -
Photo by Ser Baffo/Disney via Getty Images) -
Photo by Paula Lobo/American Broadcasting Companies, Inc. via Getty Images -
Mel B at the "America's Got Talent" Season 21 Red Carpet held at Pasadena Civic Auditorium on March 24, 2026 in Pasadena, California. (Photo by Jesse Grant/Variety via Getty Images) -
“Reverse the Curse” – Back from tribal, tensions rise following the exit of a particularly historic player. The final five immunity challenge ends in a showdown and features one of the closest finishes the show has ever seen. Jeff reveals the outcomes of the remaining in-game fan votes and how they impact the final stage of the competition. Then, one castaway will be crowned Sole Survivor and awarded the $2 million prize, during the three-hour live season finale, on SURVIVOR 50, Wednesday, May 20 (8:00-11:00 PM, ET/PT) on the CBS Television Network, and streaming on Paramount+ (live and on-demand for Paramount+ Premium plan subscribers, or on-demand for Paramount+ Essential subscribers the day after the episode airs)*. Jeff Probst serves as host and executive producer. Pictured: Aubry Bracco Photo: Robert Voets/CBS ©2025 CBS Broadcasting, Inc. All Rights Reserved.
