For our 25th anniversary, I asked my wife Jill and our three children, Hannah, Connor, and Brandon, "If there was one country in the world you could visit, where would it be?" Everyone's #1 choice was Italy. So in August 2019, we flew from Boston to Rome for a 5-city adventure. Luckily for us, friends had recommended a private tour guide for the first two days in Rome. The guide bridged the language barrier, erased the confused tourist expressions from our faces, and provided the valuable insider information we were hoping for. The guide made the major stops (Vatican, Spanish Steps, Colosseum, Trevi Fountain, Pantheon) much more enjoyable, not only because of historical knowledge, but also because they shared traveling tips, current events, and shopping advice. While enjoying an early aperitivo and a late dinner, they even shared some personal experiences that made them feel like family. The guide enhanced our trip ten fold and made it an experience of a lifetime.