LITTLE People, Big World star Matt Roloff has jetted off for a wild getaway to Cabo San Lucas, months after breaking off his nearly decade-long romance with his ex-fiancée, Caryn Chandler.

The reality star posted photos from his trip on Instagram over the weekend.

They included snapshots of Matt, 64, enjoying the sunshine and warm weather at a lavish resort, and dining with friends at various restaurants.

He appeared to unwind with his pals over drinks and even posed for photos with the excited staff.

The TLC alum also shared a pic of him sitting by the pool, shirtless, just steps away from the beach with a gorgeous ocean view.

“I love the people, the food, the sunshine and the friends i make both old and new in Cabo San Lucas,” Matt wrote in his caption.

The former TV star appeared to be loving his time away from the cameras and the constant upkeep of his Oregon farm, since LPBW’s cancellation in November 2024 and giving more responsibility of Roloff Farms to his youngest child, Jacob, 28.

His desire to sell off parts of the 109-acre farm outside of the family was a point of contention during the last couple of seasons of the show, causing a significant divide between him and his kids.

In addition to Jacob, Matt is a father to twin sons, Jeremy and Zach, 35, and a daughter, Molly, 32, whom he shares with his ex-wife, Amy Roloff, 63.

Matt’s apparent need for control is one of the things that reportedly led to his split from his ex-fiancée, Caryn, who worked with the TV personality for years on the farm before they even got together.

A source exclusively told The U.S. Sun in September that Matt allegedly frequently boxing Caryn, 58, out of decisions about his $1.4 million home, which he built from the ground up, caused tension in their relationship.

Caryn allegedly didn’t think they needed the luxurious house and didn’t feel like her input was “respected” regarding the decision-making.

Matt also had a 2,300-square-foot home in Arizona, which he sold for $20K under the asking price after he and Caryn parted ways.

The former couple had planned to spend their winters at the home in a town called Surprise, but Matt has now primarily been in Oregon.

Matt announced in July 2025 via an Instagram post that the pair had ended their engagement after eight years together.

The duo began dating in 2017, and Matt popped the question six years later; however, they continuously delayed their wedding plans.

The U.S. Sun previously revealed that they had finalized on a wedding date in May, but were forced to push it back when Matt’s mom fell ill.

The nuptials most likely wouldn’t have been filmed for LPBW, since the network had already ended the show’s 25-season run after Zach and his wife, Tori, revealed they would not be returning to the series.

They were the only ones of Matt and Amy’s children still part of the show after the others left years earlier.