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    Home » I Took 30-Year-Old Son on a Vacation to Hawaii; These Were the Rules | Invesloan.com
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    I Took 30-Year-Old Son on a Vacation to Hawaii; These Were the Rules | Invesloan.com

    June 21, 2026Updated:June 21, 2026
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    I live in New York City. My 30-year-old son, Alec, lives across the country in Southern California. When I visit, I respect that he has his own busy, adult life. While I’d like nothing more than to spend every minute with him, I’m proud of his independence and try not to monopolize his time.

    Alec has a roommate and no space for an overnight guest. When I’m on his home turf, I stay in a hotel or with a friend.

    When he comes to NYC for the holidays, his schedule is packed. Plus, with the entire family under one roof, it can be tough to carve out one-on-one time.

    I don’t feel shut out of Alec’s life, but I do miss spending quality time with him, so I floated the idea of a mother-son vacation.

    He set a few ground rules before we started planning

    Alec was vocal that for our getaway to work, we’d need to approach it as equals. This may sound deceptively simple, but it took lots of self-control on my part.

    Little kids and I pair like milk and cookies. I did my graduate studies in early childhood education and taught preschool for years. Parenting young kids is never easy, but it felt instinctive. It grew harder as my children grew older.

    Alec is my firstborn, and my parental grip was tightest around him. When he was a teenager, he told me I didn’t understand that teens needed autonomy. At the time, he was correct, but over the years, I’ve worked hard to pacify my bossy instincts.

    Allison Tibaldi

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    This time, I would welcome his voice in planning our vacation.

    Alec brought up another rule: that part of being equal should include sharing expenses. I gifted Alec his airline ticket using miles, and we split additional expenses.

    Choosing a destination

    Alec had four days off work over Memorial Day Weekend. I advocated for a location that wasn’t too hot, as I had suffered a bout of heatstroke in Greece last summer. A yoga class nearby would be a bonus.

    Alec made a case for Hawaii. He’d never been, but its laidback reputation appealed to him. He said he wanted to destress at a resort and eat poke every day.

    Hawaii is special to me. I first visited when I was a kid, spending a summer at my aunt and uncle’s home in Waianae on Oahu. The idea of sharing Hawaii with Alec was exciting.

    From a practical point of view, Hawaii made sense. There are numerous nonstop flights from LAX, Alec’s home airport. I was going to be in Denver for work, so I was already heading in a westerly direction.


    Allison Tibaldi  and her son in front of the ocean in Hawaii wearing leis

    The author loved spending time with her adult son. 

    Courtesy of Allison Tibaldi



    Each of the Hawaiian Islands has its own flavor. We had lots of options and weren’t quite sure how to narrow them down.

    Alec is a fan of the television cooking show “Top Chef.” During his online research, he learned that former contestant Sheldon Simeon was scheduled to be the visiting chef at the Ritz-Carlton O’ahu, Turtle Bay on the island’s North Shore on the Saturday night of our trip.

    The Hawaiian-born chef would be preparing a multi-course dinner using island-grown ingredients. I’m all about exploring local culture through food, so it seemed like a jackpot for both of us.

    After we booked the dinner, we figured it made sense to stay at the Ritz-Carlton.

    Balancing time together and separately was key

    Another boundary we set for our vacation was balancing time together with time apart.

    Each morning, Alec surfed, and I swam laps in the pool. I signed up for a lei-making workshop while he attended a tennis clinic.

    In a perfect world, we would have reserved individual rooms; however, we shared a room for economic reasons.

    We were still able to maintain boundaries and give each other privacy as our room had a comfortable ocean-view patio, perfect for reading and relaxing.

    Meaningful conversations are what stand out

    Time together sparked the meaningful conversations and connection I had longed for.

    On May 24, I mentioned that it was my beloved dad’s heavenly birthday. Alec shared tender memories of his grandpa and told me that my dad had been a father figure for him, too, teaching him lessons that continue to impact his life. It made me teary.

    We also had an intelligent discussion on income inequality. Alec overheard a group of vacationing doctors and a group of vacationing teachers chatting in the Jacuzzi. He said the doctors worked very long hours without complaint, while the teachers complained nonstop about their overwhelming workload. This led to a conversation between Alec and me about teachers being underpaid and undervalued.

    As a former teacher, I found that my son’s thinking about socio-economic issues that hit so close to home really resonated with me.

    Our mother-son vacation brought us closer

    Our mother-son vacation was a success. Alec ate plenty of poke. I got to practice yoga. Together, we swam in the Pacific, walked trails surrounded by gardenias, and enjoyed a delectable Hawaiian dinner.

    As much as I loved our activities, it’s the memories of our personal and poignant conversations that are etched in my heart.

    I can’t wait to travel with Alec again.

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