How We Celebrated: Our Favorite Trip Ideas for Major Milestones

Friends of mine who had honeymooned in Japan in 2018 came back raving about Kurokawa Onsen, up in the mountains of Kyushu. The following summer, on a work trip in nearby Fukuoka, I hijacked their trip for myself. The Japanese have a specific word for traveling alone: hitoritabi. The timing dovetailed well with my impending 40th birthday. When you’re that age and single, you come to a reckoning that maybe the only special someone in your life is you. The obvious solution is to bake celebration into your everyday existence.

Most of my solo trips had been the travel equivalent of sweatpants—unfailingly casual, akin to a shoulder shrug. So I took a question singles often ponder—Would you date yourself?—and wildly upped the ante: Would you honeymoon by yourself?

That’s how I ended up in that tub, taking the most memorable breaths of my life. It was a deeply intimate moment—me and the world, me with the world, me in the world. I’m amazed that the Japanese, in addition to having words for solo travel and forest light, don’t have one for the first full-body exhale of a lavish vacation. They should.

The evening continued with a 10-course dinner. “For me?!” I squealed when the kimono-clad server brought me to my private dining room. Afterward, sated, I warmed myself at the firepit, flames licking its copper basin. I slept starfish-style, which I’d like to see honeymooners attempt.

The next morning I found an outdoor waterfall bath at Ikoi Ryokan, along with a little shop where I bought a koi tapestry. But my favorite spot was the warm cave baths of the ryokan Yama no Yado Shinmeikan, whose shimmering pools spilled out in a maze of figure-eight loops. 

I’d already shed my clothes—but there in the cave, I felt the weight of other worries fall away too: of looming middle age, my win-loss mindset, and even the latent pressures of being in Japan, with its endless protocols, the bowing and highly choreographed exchange of business cards. Suddenly there was no one to please but myself, and the trip shifted into a pilgrimage to find a new me, a man of possibility more than prudence. You could hardly fault me, already au naturel, for engaging in a bit of navel-gazing.

Then, all at once, I really let go and began belting out lines from the Little Mermaid tune “Part of Your World.” “How many wonders can one cavern hold?” I sang. Just one: this glorious freedom.

I realized when I came out of my reverie that I was no longer alone. There, observing my grand performance, was a group of young, muscly South Korean park rangers on a team-building trip. They, too, were naked.

I blushed. They applauded. We all laughed and went for fried horse-meat patties, a local delicacy, at a nearby diner.

It’s not how honeymoons usually go, I know. Or heists. But perhaps honor among thieves could begin with me. I was glad for what I’d consummated on that bachelor’s honeymoon: a celebration of myself, party of one. —Richard Morgan

The bachelorette cruise

Lazy pool days, no bar tab, 10 friends, and 1,900 strangers—that was my bachelorette party. Our crew chose a three-day Caribbean sailing with Norwegian Cruise Line largely because of its all-inclusive nature, but also for the convenience of getting together throughout the day. Off the ship we explored Key West (Ernest Hemingway’s six-toed cats were a big hit) and snorkeled on Grand Bahama Island. But my favorite memories unfolded on board, in moments that felt surprisingly intimate—like discovering a quiet upper deck for sunbathing or rearranging the furniture at the bars so we could all sit together. The cruise was the ideal grown-up getaway for a group of early-30-somethings that also gave us the chance to indulge our inner kids, singing our hearts out during karaoke and tucking into late-night soft serve and fries. —Stephanie Wu

The destination wedding

For one writer, a save-the-date turned out to be more than just a wedding announcement—it was the catalyst for a never-ending family reunion.