Real world examples of intentional wandering
Have you ever planned a trip with a tight itinerary, only to feel more stressed than excited when you arrive? That’s where the beauty of intentional wandering comes in!
The intentional wandering method combines the best of both worlds: having a destination in mind while still embracing spontaneity and flexibility. With intentional wandering, you can plan for something specific—whether it’s a famous landmark or a restaurant you’ve been dying to try—yet leave room for unexpected discoveries along the way.
To show that I practice what I preach, here are a few real examples from real trips where we’ve used this intentional wandering approach to great effect.
(Click on any photo to see the caption.)
Puerto Rico, 2015
We made no bookings or appointments before the trip, which did mean that we ended up with a shitty rental car and also did not get to do any bioluminescence boat rides. But, we had an amazing trip full of lots of unexpected discoveries and intentional wandering.
We rented a car for a few days. On one of those days, we went on a road trip around the island. The plan was to go to the Arecibo Observatory and then figure things out from there, but it was closed when we got there, so we continued driving through the treacherous mountain roads, and then drove our way south west around the island, stopping periodically to grab a meal or a drink or to take photos. We met some really friendly locals, saw some gorgeous scenery and the oldest church on the island, drank award-winning margaritas, and witnessed a lot of local life. We could not have planned that day, and it is STILL my favorite day from that trip!
Rotterdam, 2016
During our month-long stay in the Hague, we spent one full day in Rotterdam, with the only plan being our appointment at a trendy new speakeasy after 11 pm. (Oh, the folly of youth.) When we arrived during the late morning, we had almost 12 hours to kill, so we just started walking in whatever direction looked interesting. That day we ended up hanging out at a super cool modern market & food hall, looking down at the city from the heights of an observation tower, stumbled upon a random festival and snuck in without tickets, and hung out with some bored sex workers at a red light district bar… all before our visit to the speakeasy! An amazing, if long and tiring, day that we will never forget!
(This was a trip that taught me a lottttttt about the importance of saying yes to the unexpected and not over-planning our life!)
New York City, 2017
The first time my husband went to NYC was for a work conference, so we obviously had to extend it a few days so he could see the greatest city in the world. We stayed in Greenwich Village, booked one Broadway show, but did not make any other plans. When we made our map of the area, however, we found that a lot of what we were interested in seeing was all within the financial district, so we had a lovely day exploring, including visiting the Museum of American Finance, which was perfectly on brand given our obsession with Hamilton. The day that we needed to be in midtown for our show, we decided to check out Rockefeller Center as our primary activity, and then spend the rest of our free time wandering the area, strolling through Central Park, stopping by St. Patrick’s, and taking obligatory Times Square selfies.
Northeast Road Trip, 2018
The intentional wandering approach is basically how we discovered DC, Philly, Boston, and Plymouth; Salem, Kennebunkport, and Portland; Montreal and Toronto. We ended up seeing SO MUCH of each city in a short period of time simply by planning our days around one particular area or site in each location. We never felt rushed or burned out, even though we spent three weeks working half-days and driving around the northeast.
Buenos Aires, 2020
At the end of a two-week cruise around South America, we spent five days in Buenos Aires. One day we explored the Recoleta neighborhood; one day we stayed in Palermo; one day we did the downtown/centro area. From the beautiful street art and architecture, to the delicious food (mmm empanadas!), affordable wine, and kid-friendly environments, we really enjoyed ourselves.
And there was so much we *didnt* get to experience: the thriving cocktail scene, the numerous museums, tango, the (free!) botanical gardens and zoo, and La Boca neighborhood. We could have probably seen all of these things had we planned out our days ahead of time and pushed ourselves to go-go-go, but it was the end of our trip and the weather was VERY hot so everyone got tired quickly. So we took it easy. I also didn’t want to stress anyone out with rigid schedules; this trip was supposed to be relaxing and fun for everyone. No stress.
Montreal, 2023
During our two-week home exchange in Verdun, we used the intentional wandering method to explore our temporary home. We never made any plans that required us to be somewhere at a specific time, with one exception (timed entry tickets for the biodome and insectarium). The rest of our days were more relaxed: we gave ourselves a destination – e.g. Mont Royal, Verdun Beach, Museum of Fine Arts – and figure out an interesting path to get us there. (Because we were traveling with a 4 year old, our path home tended to focus more on efficiency.)
Athens, 2024
When we spent a few days in Athens, the only “must do” item on our A-list was going to the Acropolis and the Acropolis museum. The rest of the time was unscheduled and unplanned. I had made my map of Athens (image 1 in gallery) and we picked areas to explore, such as the Theseio neighborhood, or a destination to reach, such as the new playground in the National Gardens. We didn’t see most of what I had put on the map (image 2 in gallery). We still experienced a lot around Athens simply by wandering around, including so many things I didnt even put on the map: a flea market, several delicious restaurants, and ruins. We admired the old ruins and monuments, we cooled down in shady parks, we ate our weight in taziki sauce, we pet every feral cat we met, we wandered through crowded streets of tourists and quiet residential roads. And we spent a lot of time relaxing on our balcony, staring at the acropolis, drinking Greek beer and eating Greek snacks. No one got burned out from trying to do too much in the short amount of time that we had.
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