The Colosseum in Rome. The Blue Mosque in Istanbul. Big Ben in London. There are certain iconic sights that you simply “have” to see when you visit destinations. But what about relaxing, exploring, and immersing yourself in the local lifestyle? (This is a vacation, after all.)

Some would argue that the magic of traveling lies in those unexpected moments and through truly experiencing a place through all your senses—and they would have a point. There’s nothing like the laze of sunbathing on the shores of Majorca, napping through the heat of the afternoon alongside locals, or the contented leisure of reading a book for hours in a café, as Parisian daily life bustles around you. When it comes to planning a vacation, it seems like travelers often fall into two camps: the stick-to-the-itinerary traveler and the let’s-see-where-life-takes-us traveler. I’d argue you...