On the first day of vacation, Kim Kardashian, who is 5 months pregnant now, along with her sisters Kourtney, Khloe, Kendall, and mom Kris Jenner, touched down in St. Barts on Monday, Aug. 17. The first thing in their itinerary was some shopping therapy.

As they strolled down the Caribbean island's town, the Kardashian-Jenner clan were dressed in their best resort wear. They had the E! camera crew in tow. The trip marks the "Keeping Up With the Kardashians stars'" annual family vacation, which is featured each season on their hit reality program.

Kim opted for a comfortable-looking black maxi dress and flat sandals, while showing off her baby-bump. Khloe, who slimmed down recently, matched her famous older sister in a more revealing black maxi. It showed off a hint of sideboob too, according to US Magazine.

Kourtney, 36, is noted to be dressing more sexier after her split with her longtime boyfriend, Scott Disick, in July. She opted for a chic white cover-up and gold gladiator sandals, according to the magazine.

Kris, wore a floral print dress while Kendall showed off her model bod in a printed two-piece ensemble. Following the footsteps of her Kylie, who will be joining the family on their trip Tuesday, Aug. 18, the 19-year-old Kris kept her locks out of her face in cornrows.

"At one point during their excursion, the Fendi model and Lamar Odom's ex ventured off from the group for a moment and goofed off on ATVs," the magazine reported.

According to sources, Kim's husband, Kanye West, and Kris' boyfriend, Corey Gamble, are also set to join the family.

The children: Kim's daughter, North West and Kourtney's three children with Disick: Mason, Penelope and Reign Disick were a part of the tropical vacation.

Khloe posted an adorable picture on Instagram, in which little Nori wears mom Kim's oversized sunglasses while clutching a glass of water. "MOOD," the doting aunt captioned the snap.