Planning for spontaneity: Italy

[Polignano a Mare // Sorano/Trentino // Sardinia/Santa Maria al Bagno]

We’re going! We’ve booked our tickets—three and a lap-infant—to Italy for the end of summer! Italy has been on our minds since our trip to Sardinia, as you might recall.

In her editor’s letter in the revamped Condé Nast Traveler, Pilar Guzmán, said something that felt so spot-on for me and how I like to approach traveling: “Sometimes a truly memorable trip is the one when the unexpected happens, when you get lost in a good way. But spontaneity takes planning, gathering, and the collective wisdom of travelers you trust.” So many of you have already left such helpful comments, so I’m hoping I can solicit your collective wisdom again.

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We’re flying into Rome and out of Naples, staying put for the first 3 nights and ending up on the Amalfi coast for the last 6. There are 9 nights free in between. We’ve been thinking about renting a car to leave Rome and driving into Tuscany or Umbria for half, and then south to Puglia for the other.

For the Tuscany or Umbria portion, we’re undecided about where to base ourselves. Town or countryside? We’re not planning on returning to Florence on this trip and are considering staying out of the larger towns. Though we’ve never been to Siena (with its car-free piazza… good for toddlers!), and many have suggested we stay there and then do day-trips. Or there’s the option to stay at a rented home in the countryside and do day-trips from there? But will I miss waking up and strolling to a bakery or cafe and start to lament always having to get kids into the car to go somewhere? Maybe it would be best to stay in a very, very small town to have the best of both!

The second part of the equation is our (slightly irrational, we’re being warned) desire to split those 9 days into two parts. I’m sure we could happily pass the entire week in Umbria, but I’ve always been very curious about Puglia, down in the heel of the boot.

If it were just Aron and I, I wouldn’t hesitate for an instant. But I do wonder if the extra drive-time and moving about will be worthwhile with a three-year-old and six-month-old. At the same time, I feel like our interests for each day are actually rather unambitious. We’re fairly content to get our culture from strolling along streets, tasting gelato, enjoying the views; there aren’t going to be a lot of museum visits and duomo tours in our plans.

Any thoughts? I’d love to hear. I was slightly alarmed by some discouraging comments I got on the Fodors forum. (Am I crazy?) One reader commented: “The only way I would suggest this itinerary is to leave the kids home with Grammy. Too much exposure.” Yikes!

[Civita // Praiano // Positano // Rome // Montepulciano // Sorrento/Rome // Sardinia]

If you’ve been, where would you base yourself? Tell me your favorite city (or the city you’d most like to visit) and whether you’d choose to base yourself there. Weigh in. Better yet, if you’re game, I’d love to try something new:

Share a photo of your favorite place in Italy (city, restaurant, market, beach, whatever) on your Instagram, Facebook, Twitter, or Pinterest (whichever you like to use most) with a caption and the hashtag #ItalyHitherThither (throw in @AshleyMuirBruhn to be sure I see it) and I’ll come back and share the “collective wisdom of travelers” (with photos and credit) in a future post. Collaboration in the name of future spontaneity. Sound good? 

P.S. Our first Italian Travelogue. And some thoughts on itineraries.

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