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From the secret subway station beneath City Hall to the Met’s kid-sized period rooms, old-school toy shops and children’s bookstores, and the date night spots worth calling the babysitter for.

In the endless quest for the family beach getaway that’s easy yet tasteful, designer Naina Shah combined two very different stays on the Yucatán coast: one social and polished, the other slower and more elemental.

From annual 10-hour flights to Greece with twins to dinners in Madrid that stretch well past bedtime, Ali Alquiza Klidonas brings her hard-won expertise to our family travel column.

Looking for an adventure over New Year’s, Hannah Bronfman and her family headed to the low-key island of Bequia. The kind of place where kids can run around on the beach while parents supervise from a distance during long, toes-in-the-sand lunches, and happy hour means rum and Cokes set to a soundtrack of soca music.

Restaurateur Brooks Reitz set off with his wife and young son on a road trip that stretched from the palm trees of LA to the apple orchards of Philo, winding through Ojai, Carmel, Inverness, and beyond.

The twin towns of Deauville and Trouville-sur-Mer on the Normandy coast have long lured Parisians for their buzzy restaurants, Neo-Norman architecture, and sandy beaches sprinkled with candy-colored umbrellas. Maddy Odom made the easy trip from Paris for a few laid-back days of shell-scavenging and sandcastle-building, waterfront meals of fresh oysters, (plus a detour to Giverny!)…

For his daughter’s school break, Martins Pilens decided to revisit one of his favorite places through their eyes. With thrilling water taxi rides, nightcaps of gelato (for the kids) and Americanos (for the parents), and a picnic in the garden of a Palladian villa, the trip was equally fun for all.

Nanda and Max Haensel set off on a 2,500-mile loop through Southern Chile and Argentina with toddlers in tow—no screens, just crayons, picture books and the open road. Along the iconic Ruta 7, they discovered that the planet’s wildest frontiers can stir a sense of adventure and discovery, even in the smallest travelers.

Looking to create a life-changing adventure for her 6-year-old son, Alix Massimo di Roccasecca’s rules were to travel light, stay only in small soulful hotels, and to leave much of the trip unplanned—following tips from people they met along the way.