Summer Travel Planning: One City, One Beat (And How I Actually Plan It)

J. wants to see everything. She always has. The moment we land somewhere, especially Italy, especially any city, she is already referencing her list. Ten things before noon. Four cities in a week. All of the museums. All of the cool neighborhoods. She is fifteen but moves like a twenty-five year old. Taking the subway in Tokyo solo with friends. Making dinner reservations at hotspots in New York before bookings at Broadway shows. She snags concert tickets in any city we find ourselves in, sending a flurry of Ticketmaster linked texts. She knows how to move through the world and makes up for our quieter, more bucolic lifestyle on Maui the minute our feet hit the pavement. One day, she says she will move back to New York. She says it is where she belongs. I believe her.

But for now, I am just trying to keep up. Without her driving energy, my husband and I would probably travel very differently. We’d move a little slower, taking things in a little more intimately. We’d probably do fewer cities in any given country. There would definitely be longer mornings and shorter nights. But watching her, particularly in Italy and New York every summer, drop into the driving flow of our hometowns with confidence and excitement and poise is one of the great privileges of our lives. So we follow her lead. 

And after the fires, that instinct intensified. When that kind of trauma happens, when your sense of reality is rocked this way, something inside of you just wants to say yes to everything, to beauty, to movement, to the way that your daughter's face lights up when she rolls up on the Duomo in Milano. So that year, we built the trip that she’d always wanted. Milan to Naples, nearly the whole country, working our way down. First, the family. Then Florence, Siena, Bologna, Rome. Naples, for more family. We even added a stop to the Amalfi Coast because it was on the way. 

It was a lot. The flying. The driving. The walking. Dragging heavy luggage up and down narrow, ancient streets not meant to accommodate the conveniences of modern travelers. By the time we got back to Maui, I was shot. The opposite of restored. I felt overstimulated and hollowed out. Like we’d seen everything but absorbed very little. Like we “did” Italy instead of experiencing it fully. Back on Maui, we were barely able to gather ourselves to show up for our real lives. We were exhausted.  

So last summer, we did it differently. For one, our little house near Naples was ready. We had an anchor and an aim, with fewer cities on the agenda. And the ability to spend more time in each one. Firmly rooted in the south, we ventured out to Naples, Bari and other small towns in between. Spending rich days with our family at home, we relished the slower pace and the simpler food and the languid nights gathered around the table. And somewhere along the way, on that particular trip, I intuitively understood what I had been doing wrong.

I had been building itineraries. I should have been building beats. More than just a stop on a map. Each city needed to play a different note, perform a specific function, color the trip in a unique and special way. Now, one city’s plan could be built around a reason or a vibe or a goal. Planning that way, focusing on one singular experience at a time, with each city selected for one clear purpose, makes a trip more than just a list of locations. Intention for each destination makes each stop feel more like a note in a greater song. 

For instance, Florence sings of creativity. I lean into that energy before I put a single thing on the agenda. It’s the Renaissance art for me, the almost obsessive pursuit of balance and symmetry. The representations of the cultural belief that beauty and truth come from the same source. A sense that I don't always know I need until I'm standing in front of something very old and very beautiful. History is long. Life is short. Make it count.

So now, when I plan our summers, I am more intentional. The process unfolds in little pieces, over time, without pressure. Out on the lanai, usually. By the pool. Under weather so unreasonably good this time of year that I am almost tempted to just stay. Sometimes searches start at night, when everything else is done, with my husband beside me or J. drifting in to weigh in and the planning becomes a conversation, a debate, a negotiation. I love those kinds of nights. But either way, this kind of building is best executed in small swatches of time, not in marathon sessions, no stress. A little research here, a few pins dropped on a map there, a flight comparison in a quiet fifteen minutes respite between to-dos. It all adds up. One day it's a trip.

I use a combination of Apple Notes and iCal to anchor each city before I touch logistics. Not a spreadsheet. Just a note titled with a city and a purpose. Florence: Creative Reset. Rome: Energy, Ruins and Restaurants. New York: Grounding, Connection, Exploration. Once I give each place a purpose, I move to Google Maps and start dropping pins, not building a minute-by-minute schedule but defining a rhythm and a flow. I run any extra flights through Google Gemini's Personal Intelligence because it knows how I like to travel, where I'm coming from, what routing makes sense, what I'll actually tolerate. This saves a lot of time. And the return flight is already booked. I talked about that yesterday. Everything else builds inward from here.

So here's what I know after all is said and done, after the overstacked summers and the fires and the rebuilding and the trips that emptied me out and the ones that filled me back up: The plan is only a guide. A wish. Leave room, because what actually unfolds is always better than anything you could have anticipated. Your job is to be present enough to receive it. And you cannot be present in six cities. You can only be present in one. At a time. 

Give each place a beat. Listen to its music. Drop into its rhythms. You might get pushed a little past your comfort zone. Be open to that. Trust that the melody you have written will hold.

One city. One beat. Then on to the next.

How does a city earn a place on your itinerary? I’d love to know how you decide.