One thing that this forum has taught me over 15 years here is the craft of doing it yourself. Either directly through posts/responses or via a suggested link, I've pretty much been able to achieve my goal of self-sufficient travel. You guys are the best at allowing us to do our own thang.
But in the sometimes-exhausting role of de facto tour guide--even if it's only wife & myself, I have come to realize that, at various points in a trip with multiple destinations, it is nothing short of a wonderful feeling to hand the car keys (i.e. decision-making) off to a good guide for awhile. This practice worked famously on our trip last April, from a wonderful day in Chianti with the Accidental Tourist folks, to a fledgling driver husband and guide wife that carted four of us around the Amalfi Coast on a day that was approaching gridlock for normal mortals, to my friends at Sicily Life that took us up the winding roads of Etna amongst the banging & booming of an active volcano. All of them memories to last a lifetime.
So that is why I'm starting early to secure a guide/driver for our next trip in March 2027, that will begin with a chill couple of weeks in Rome, then via Trenitalia to Puglia, where we haven't yet been in four previous trips to Italy. I'm thinking a week basing in Lecce, taking the train ourselves during the day to Bari & back, stopping occasionally along the way to check out places like Brindisi, Monopoli, Polignano a Mare, and grooving in Lecce's Old Town in the evenings.
But one day I'd like to hire someone local, preferably personally-recommended, to take us inland, maybe to Ostuni, Alberobello and finally Manduria, where a few years ago my brother witnessed a tree planted in my father's honor because his Air Force squadron based there in WWII--he told me the Mandurians are forever grateful for my dad's service. Can't miss that. And I'd like that guide to possess the kind of inside knowledge that only a resident would have.
I know a private tour like this isn't cheap, but in my travels even though I've always been value-driven, as I think most of us on this forum are, I certainly don't mind paying for quality. Chime in with any personal recounts of travels in the vicinity and/or experiences with worthwhile guides. Thanks!