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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.

Skiing in Italy—a father-son bonding trip that’s more affordable and accessible than the American West, with way better food