Vanessa Grimaldi‘s son, Winston, has turned three years old and the Bachelor Nation alum celebrated by taking the little guy to Disney World. Heading to the happiest place on Earth with the birthday boy as well as Vanessa’s husband, Josh Wolfe, the loving mom took to Instagram to shares a few pictures of the trio.
In the first video, the family can be seen together at the Disney park while Winston look a little groggy. In the caption, Vanessa explained why, writing, “When you wake up 3 in Disney World ❤️🥹🥳”
“Ps. You will always be my baby! 😭,” she continued. “Happy 3rd birthday, Winston!! 😘”
In the comments, she added, “How are you already 3!!!😭”
“Happiest birthday to my sweet boy!!” she also wrote. In a third comment, she added, “Disney for the win!!😍”
In the collection of photos and videos, the family can be seen experiencing the perks of the park and having a wonderful time doing so. That is, when Winston wasn’t having a little nap.
Followers Sent Winston Birthday Wishes
Vanessa’s post sparked plenty of comments that were filled with well wishes for Winston. One person wrote, “Oh my happy birthday to your beautiful Boy. He will always remember this birthday. So so magical. Even for grown ups. Love ❤️ enjoy making tons of great memories ❤️”
“Happy Birthday to your big boy! Geeze already 3 🥳🎉💙Enjoy Disney land😍,” someone else left in a comment. Another follower wrote, “Can’t believe he’s already three 😭❤️ What a beautiful birthday it was!!”
“So sweet!!,” wrote fellow Bachelor Nation alum Raven Gates Gottschalk.
Vanessa Has Opened Up About Motherhood
Vanessa has opened up in the past about what it means to her to be a mother and have a little one.
“I love my husband, so in love with him. He’s the greatest human being in the world. But the second I had my son in my arms I was like, ‘I’ve never experienced a love like this in my life,'” she told Us Weekly in April 2025.
“And even now he’s two and a half, he’s able to express himself,” she said. “He’s able to engage in conversations and reason. He’s witty and he’s a very sweet boy and he gets that from his father.”
She also talked about his age, saying, “No terrible two situation yet. He’s two and a half, he’s going on three. So maybe we just completely skipped the stage.”
