Two Single Moms, Four Kids, and a Trip to Oahu Made for the Perfect Family Vacation

The trip broadened my horizons in ways I didn't expect

Affectionate lesbian couple and daughter at remote, sunny, summer poolside in countryside

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We’re dedicating our March features to family travel. Read on for insightful guides to the best road trips for different ages, the best hotels with amenities for children, and the changing face of family trip planning, as well as inspiring stories of traveling with a newborn, family travel post-divorce, the lowdown on family campground culture, and more.

Melissa and her son Ben were the last people I thought I’d be vacationing with on Oahu. She and I met at the quintessential intersection of work, art, and life. Although we’d never actually interacted during our time together on Valpo’s campus, we were both in the Chicago Arts Program. This study-abroad program had us living on the luxurious Gold Coast in the third-largest city in the United States. We explored arts performances, made field recordings, and navigated internships together. It was a transitional time that launched our careers and lives into adulthood, which is a perfect backdrop for how we ended up on this unlikely family trip nearly 20 years later.

What seemed impossible for us individually was totally plausible if we could figure it out together.

I'm serious about my love for Hawaii, having visited every year of my almost 14-year marriage. At the end of 2019, when my marriage ended just months after an epic Kauai trip with our family of 5, my daughter was sure that this tradition would end. At dinner one night, as I checked how they were feeling about the divorce, she boldly proclaimed, "We probably won't even go to Hawaii anymore."

I checked myself so that I wouldn't overreact, but inside, I was like Nettie from "The Color Purple," peering back at Celie in full voice, "Nothing but death could keep me from it!" I assured her we would keep our tradition.

However, COVID-19 did indeed keep us from Hawaii for a year, but we were able to return this past June. During a quick catch-up call, Melissa and I hatched a plan to travel in the middle of a pandemic. What seemed impossible for us individually was plausible if we could figure it out together. And so we went forward with a plan to visit Oahu: two single moms, four kids, all with sun and fun on our minds.

I call it a hybrid trip. It was both a family trip and a girls' trip. Melissa and I were there to reconnect after not seeing each other for over a decade. We'd been married and divorced in that time, had become moms, and had careers. We were also very much on the same page.

Being on the same page about what we wanted to do and not do, kept conflicts at bay. While in college, we'd witnessed drunken classmates, had some shady dealings when meeting guys, and had some experiences out and about that can't be shared here, but this trip wasn't going to make the news. We both centered the kids' experiences as a priority. Our values for this trip were fun, service, good food, good company, and memories.

Being on the same page ... kept conflicts between us at bay.

The biggest hurdle to traveling as a single parent is cost, so we stayed together at two different family-friendly hotels over four days, both of which had two-bedroom suites. The Sheraton Waikiki Hotel was more like a resort, with kids' programming, a giant waterslide for the kids, and direct access to Waikiki Beach. We also stayed at Aston Waikiki Beach Tower, which is still close to shops and the beach, but much quieter and has more upscale amenities and personal service.

While we stayed together, Melissa and Ben arrived a few days earlier than my family, giving them the chance to spend with friends living on Oahu. This meant that we experienced Polynesian Cultural Center (PCC) and the Aha'aina Luau at the Royal Hawaiian separately, which was probably for the best. The chill of Melissa and Ben, age 6, may not have been as attuned to the activities or food as much as my high-energy kids, who'd been to both before. By attending separately, Melissa and Ben could make their own memories and move at a pace more suitable to them, while my kids did the proverbial most at both events.

Of course, there were hiccups with transportation, as the car rental shortage has taught Hawaiian travelers of all stripes. A flub on my part with securing the right size vehicle for all of us meant we mostly used public transportation and ride-hailing services. Given that we were with kids, and this being my first time without my own rental car, I'd say I preferred not having to drive. It allowed us to walk more, talk more, and interact with the kids as we made our way around the island.

Traveling as a single parent wasn't as scary as I thought it would be.

Focusing on service meant acknowledging and highlighting the aina (the land) and helping our children think about their impact on the world. An exhaustive search led us to the Malama Hawaii program, which gave an extra night hotel stay for volunteering at certain places on Oahu.

We visited Gunstock Ranch, where we each planted a tree and learned that we were making our trip to Hawaii carbon-neutral by planting a tree. We also visited Sea Life Park, which supports conservation efforts for sea animals and plants. We fed love birds, sea turtles, and fish and watched their dolphin show there. But we also showed the kids the importance of limu (sea algae) and the work Sea Life Park is doing to protect Hawaiian monk seals. Of course, the children were into the shows, but getting up close to the trainers and scientists who run the park was a valuable new experience for them.

A resting Hawaiian monk seal on the beach of Kauai, Hawaii

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Traveling as a single parent wasn't as scary as I thought it would be. Having a new friend meant my kids' sibling rivalry wasn't half as bad as usual, and having my friend Melissa there to make new memories was better than I imagined. Travel talk used to only be with my significant other, but now it can be had with some close friends. This trip broadened my horizons about what's important not only for my children to see but for my friends as well. I want them to know that they are loved and appreciated, and meeting them in Hawaii sounds a lot better than catching up at a dive bar down the street from our old high school.

Our trip was a full-circle moment that changed my perspective on family travel and how I view the girls' trip I always longed for. While I'm not sure she'll have me, I'm eyeing Melissa and Ben for our next excursion, likely to Costa Rica. We're getting the passports in order now, and hopefully, we'll find a mountain top and a stretch of beach to enjoy together.