My Family and I Splurged on a Charter Yacht Vacation — and It Was Totally Worth It

For 10 years, my best friend and I have teamed up to take our six children on rustic, inexpensive summer trips, leaving the bougie dads at home. But last summer, with the two oldest kids about to go off to college, everyone agreed it was time to upgrade — and that enticement got even the sybaritic spouses interested.

The consensus was to charter a yacht. We budgeted $50,000 for the week, or five grand a person. A handsome sum, to be sure, but this was to be our group’s last hurrah. One friend, a seasoned yachter, connected me with a broker, while another helped us chart the perfect itinerary through the Cyclades. By the time we landed in Athens, we felt as glam as the Kardashians.

Which lasted all of two minutes. Our skipper, Dimitris Altanis, greeted us with bad news: one of the toilets on our yacht was broken, and we’d need to wait out the hours- long repairs on a mediocre urban beach. Meanwhile, one of the cabin attendants left the boat to attend to a family emergency. Then came the weather report. Fierce winds, known as the Meltemi, had kicked up, meaning there was no way we could do my carefully planned itinerary — at least not comfortably. There’d be no Mykonos, no Páros, no Naxos.

Had we made a huge mistake? Not at all. The captain and the remaining crew sprang into action, and by evening, we were on our way aboard the Gioe I. On our first night, we discovered the singular rule of yacht charters: the boat is the destination. Under moonlight, the staff unfurled floating foam mats off the stern. The 10 of us jumped on and started a chicken fight, kids versus adults. Our laughter echoed across the Saronic Gulf.

Every morning, we’d jump into the sea from the top deck before indulging in a long, breezy breakfast prepared by chief cook Kalomoira Kaltsa. Then we’d read or play Bananagrams or try our luck at snorkeling off the swim platform. In the evenings, the Gioe I was often the sole vessel at anchor in some beautiful cove, so we would fire up a dance party.

Not that we didn’t go ashore: we visited Epidaurus, home to a stunning ancient amphitheater; Paralio Astros, with its centuries-old castle; the island of Spetses, where we rode in horse-drawn carriages past the Venetian mansions of the old town. Whatever shenanigans we conceived — like betting the kids $200 they couldn’t scramble to the top of a steep summit — the crew was right there for us. They’d happily help with everything from salvaging a cell phone stuck beneath a rock to grabbing more sunscreen for our rapidly bronzing teens.

The blissful week was meant to be the final farewell to our two-family adventures, but this winter we started looking into another, maybe to Croatia. We might even convince the dads to join us.

A version of this story first appeared in the June 2023 issue of Travel + Leisure under the headline “Yachts Rock."