I have a friend whose parents were not the traveling types. Not that they didn’t love the idea of traveling to new lands and sipping wine on exotic beaches... It’s just that many years had come and gone without the opportunity to take a big, exciting trip abroad.

Last spring, they finally decided this was going to be their year: they were off to explore the romance of Italy. Knowing her parents had never done anything like this, and being a seasoned traveler herself, my friend recommended they might try a pre-planned vacation — a packaged trip that would take care of the nitty-gritty: designing an itinerary, booking hotels, making restaurant recommendations, setting schedules, etc.

But my friend’s mother was convinced she could do it herself, and she threw herself into months collecting train schedules, combing through customer reviews, and printing out small maps.

But on the ground her plans sadly became unraveled. Her time tables didn’t account for obscure Italian holidays. Once-famous gelaterias had closed shop or turned over to new management. Ferries that looked quaint and charming online turned out in person to be just plain dilapidated.