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On Failing the Family Vacation

by Staff

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Updated at 10:30 a.m. ET on February 15, 2024

I wanted to go on a perfect family vacation this past Christmas, even though my family had fallen apart.

As a daughter, a wife, a mother, I’d never pulled it off, never experienced that joyous, together-away adventure that seemed to come so easily to others. When I was a child, it was on family vacations that I first contemplated running away from home. When I was married, it was on vacations that I first contemplated divorce. Once divorced, it was on vacations that I questioned the soundness of my new relationship.

This year, I told myself, it was going to be different.

I booked myself, my two kids, and my partner-boyfriend (I thought of him as somewhere between the two), on a Norwegian Cruise Line mega-ship bound for Mexico, Honduras, and Belize. Despite the bad rap cruises have for their norovirus outbreaks and abominable carbon footprint, and despite all of the funny, damning things David Foster Wallace wrote about them, a cruise still seemed like the best option. I’d invited my parents and my sister’s family to come along, and I couldn’t imagine coming up with one destination that would satisfy everyone. Also, I had gone to graduate school to become a therapist, and I’d learned that anxiety arises from our conflicting desires for autonomy and connection. Cruising, a kind sales rep named Kristen or Crystal or Karen told me, offers both: “Everyone can explore on their own during the day, and then you can come together for meals and entertainment at night.”

When I told her about my struggles with family vacations, she said, “That’s why I only travel with my gay best friend. But I have a good feeling for you. I have a feeling this is going to be the trip.”

“Family vacations aren’t about the room you stay in,” my father always used to say. “They’re about seeing new things and bonding.”

One budget room for the four of us meant that I learned that my sister slept in a bra, that my father had sleep apnea, and that my mother clipped his toenails. Our parents filled the room with medications and snacks: ibuprofen, bug spray, hydrocortisone, dried fruit, peanut butter, saltines, packets of Crystal Light, and, stored in the minibar beside the off-limit cans of cola, my father’s insulin.

The emotional tenor of these family vacations was not one of adventure or togetherness but of tension and confinement. My mother always wanted everyone to have fun, but her emotional triggers were getting lost and spending money—two unavoidable aspects of traveling. She seemed to have an idea in her head of how much things should cost and how long they should take, and when reality pushed up against these ideas, she’d yell at my father and make unreasonable demands of hotel clerks and servers in languages they didn’t understand, while I did my best to pretend that I was not a member of the family but some solitary 10-year-old wandering the globe.

If I ever had a family of my own, I thought, I’d find a way to do it better.

For a while, I thought I had. My husband’s family took great vacations. Every Christmas, his father would plan a trip somewhere luxurious. There were infinity pools and rainforest showers and beachside daybeds. Once, I looked up from an alfresco breakfast to see Malcolm Gladwell sprinkling capers onto his smoked salmon. On Christmas Day, Santa Claus appeared out of the sky along with half a dozen skydiving elves, all of them landing on the beach to throw presents at our awestruck Jewish children.

Spoiled as we were by this White Lotus treatment, it wasn’t the thing, or at least not the only thing, that made the vacations special. My husband’s family had figured out a way to be away together, to create ritual and tradition around family leisure.

And yet, those days in paradise were also some of my loneliest. My in-laws were a loving, generous family. But they never felt like my family.

The loneliness ebbed a little the year we brought along Beth, a friend of mine who worked as a babysitter. The best times I had were when the two of us snuck off after bedtime for margaritas by the pool. We laughed about things we’d observed that day, such as the man who’d bribed a bartender to help his kids cut the line for their photo op with Skydiving Santa. If I could make fun of this place and the pampered housewives who stayed there, I thought, then I surely wasn’t like them.

But if I wasn’t like them—if I didn’t belong on vacation with my husband’s family or with my own—then where did I belong?

After 16 years of marriage, my husband and I separated and were each soon seeing someone new. The first winter it was safe to resume traveling after the coronavirus outbreak, I decided I wanted to plan a vacation for me and the kids (then 11 and 14) and my boyfriend. I wanted to prove to myself that the new family or half-family we had formed could take a vacation of our own. So what if my boyfriend, who’s younger than I am, had never really traveled with kids before? So what if I couldn’t afford a resort with Skydiving Santa? Family vacations aren’t about the room.

At Costco, I bought us a package deal to Puerto Rico. The flight landed in San Juan at 4 a.m. Standing in line to check my luggage, I opened a portable packet of hand sanitizer in a way that caused it to squirt directly into my eye. “My eye! My eye!” I yelled, screaming for water. Someone handed me a bottle of Gatorade. Things went downhill from there.

We waited, dazed, in the hotel’s moonlit lobby until our rooms were ready. The pool was pristine but freezing. “You just have to swim fast,” my daughter said, the color draining from her lips. Everything we wanted to do was far away from the hotel; I’d failed to rent a car in advance, and none were available. My daughter tried zip-lining and nearly mangled her right hand. When my boyfriend and I had an argument, he refused to go on the bioluminescent kayak excursion with us.

Paddling through warm rain and mosquitoes and discarded glow sticks, I heard my daughter’s voice say from behind me in the kayak, “Why are we doing this?”

Two years later, I was ready to try again. My boyfriend agreed. The kids loved the idea of sleeping on a ship. My parents were experienced cruisers and thought it sounded fun, and my sister said she was up for it, as long as she could persuade her husband.

“I can’t persuade my husband,” she told me a few months later. He was on a health kick and wouldn’t consider any vacation where the main activity was eating. My parents were the next to bow out—my mother was not in good enough health to commit to something in advance. So I downsized my expectations. It wouldn’t be the big family vacation I’d hoped for, but it could still be a good family vacation.

I got the cruise line’s app on my phone and obsessed over meal plans and excursions. Every time I opened the app, a countdown widget appeared, showing the days remaining before we set sail. The day it got to 86, my boyfriend broke up with me. He left that evening with his guitar, his iPad, and the shredded carcass of my heart.

Four days later, when I got out of bed, I remembered the vacation and called to see if I could get refunded for his portion of the trip. Another kind sales rep apologized to me. A week ago, I could have, but now I’d passed “the point of no return.”

The point of no return didn’t sound good to me at all.

She had only empathy to offer, and some cutting remarks about men. Even though it was too late for a refund, she told me, it wasn’t too late to make a swap. Maybe I could bring someone else?

“I don’t have anyone else,” I said, weeping.

But a few weeks later, I had an idea. I called up Beth, my babysitter friend, and asked if she would be my family for our vacation.

A cruise ship filled with 3,100 family vacationers is a strange place to spend Christmas as a 45-year-old woman who has tried and failed the nuclear-family project. Lately I’d been reading about Tibetan Buddhism’s teachings around nonattachment—specifically, the practice of meditating among the corpses of the charnel ground. Over those seven days and nights, I began to think of the cruise ship, with its phantasmagoria of family bonding, as my charnel ground—husbands and wives and children and grandparents and aunts and uncles eating and swimming and riding speedway go-karts and sitting for family portraits and going to see Summer: The Donna Summer Musical. It was like everyone in the world was enveloped by a big nuclear family, except for me and my kids. But I would just have to do what the Buddhists do: accept what I most feared, and go forward into the void.

Sitting on the top-floor observation deck as the sun set one night, my son put his hand on my shoulder and asked if I was sad about the breakup.

I took a breath. “I am,” I said. “But mostly I’m happy to be here with you.”

It wasn’t a perfect family vacation, but it was okay. My daughter learned to scuba dive. My son roasted sea bass (and snuck a margarita) over an open flame on the beach. Beth and I ate a lot, read in the sun, and talked. We never went to see the Donna Summer musical. I cried only once, under a poolside cabana, the tears sliding down my already salty cheeks.

Gradually, lounging among my own dashed hopes, I began to understand that no family vacation was going to change who I was. I just wasn’t well suited for many of the conventions of family life. I loved my children and would always be there for them. Maybe that was the most I could manage. Maybe that was okay.

On the last night of our vacation, Beth told me that the secret of being a single woman is that “it’s actually not hard at all. Being in a relationship is hard. Being married is hard. As long as you have a community and good friends, being single is easy. But you have to pretend that it’s hard. You have to pretend that you’re sad and lonely, because otherwise every woman would want to do it, and then society would fall apart.”

The next day, we said goodbye at the airport, and 10 minutes later, she texted me: “I love you. We did it.”

“I love you too,” I wrote back. “Let’s never do it again.”

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