Let me begin by saying I’m not much of a planner. I’m more of a “fly by the seat of my pants” type of person. When I see something I like, I buy it (which is why my closet is overstuffed and I love the look of Boho in my home). It’s a “if I like it and I see it, I buy it” mentality. The same goes for my travel. I may decide on a location and have no choice but to choose a hotel (because I know I’ll have to have a place to sleep), but other than that, to me travel is GO WITH THE FLOW. As a result, I often find myself traveling with companions who love to plan (maybe out of frustration with the way that I travel, maybe because they’re just natural organizers). I am happy just wandering a neighborhood, getting lost, sitting and having a coffee, smelling the aroma of a nearby bakery, listening to the cacophony of the chatter
Why leaving room in the itinerary can become the best part of the trip
I used to think a successful vacation was one where I could look back and say, “We did everything.” Every landmark, every restaurant someone recommended, every museum, every photo stop. If there was a free hour on the itinerary, surely I could find something to put in it.
After years of travel, I’ve learned that some of my favorite moments happened in those free hours.
I remember the places I wandered into because I had nowhere else to be. I remember sitting over a meal long enough to notice the people around me, and hearing music spill through an open doorway while I walked down a street I hadn’t planned to visit. I remember the pleasure of going back to a hotel room in the middle of the day, changing clothes and setting out again because I wanted to, not because the schedule told me to.
I still love a full day. I’ll get up early for an experience I’m excited about, and I certainly don’t travel to spend every afternoon in my room. But I’ve become much more careful about how I fill my time. The trip feels richer when I give myself enough space to enjoy it while it’s happening.
The pressure to make every minute count
Travel takes planning and money. If it’s a place you’ve dreamed of visiting, the urge to see absolutely everything is understandable. You make a list, then another list. Someone sends you a restaurant recommendation, a friend insists you can’t miss a certain attraction, and a video shows you the “hidden gem” that apparently everyone else has found, too.
Soon the vacation begins to look like an appointment book. Breakfast at eight. Museum at nine. Lunch at noon, if the museum line cooperates. An afternoon tour, a quick change at the hotel, and dinner reservations you have to rush to make. There’s nothing wrong with that day if it sounds wonderful to you. I’ve had days like it myself. The trouble comes when every day looks like that, and you reach the end of your trip needing another vacation to recover.
For me, doing less isn’t about seeing less of a place. It’s about being present for what I chose to see. If I’m thinking about the next stop while I’m still at this one, I’ve taken the fun out of both.
I may give each day one main event
My simplest planning trick for someone just starting is to choose one thing that matters most each day. It might be a tour, a restaurant I’ve been looking forward to, a visit to a neighborhood, or simply an afternoon by the water. That one thing would get a real place on the calendar. Everything else is an option.
If I have the energy and the mood strikes, I can add something nearby. If a conversation runs long or I find a shop I love, I don’t have to pull myself away to stay “on schedule.” I can always keep a short list of possibilities on my phone without turning every possibility into an obligation.
This works especially well on a cruise. In a port I’ve never visited, I might book an excursion that takes me somewhere I couldn’t comfortably reach on my own. In another port, my one plan might be to walk, find a place for lunch, and enjoy the fact that somebody else will be driving the ship to the next destination. Both can be wonderful days.
The key is deciding what kind of day I want before I start adding activities. Am I eager to explore, or do I want to slow down? Am I traveling with someone whose idea of a good vacation is different from mine? A good itinerary has room for those answers.
I leave space for the place to surprise me
When every hour is spoken for, there’s little chance to follow your curiosity. That’s a shame, because curiosity is one of the best reasons to travel.
Maybe you planned to spend twenty minutes in a neighborhood and discovered you loved it. Maybe you found a café that looked far more inviting than the lunch spot you saved weeks ago. Maybe it rained, and the afternoon you thought was ruined turned into an unexpectedly lovely hour indoors.
You can’t schedule those moments. You can only leave enough room for them to happen.
I like to research a place before I go. I want to know what’s possible, and I especially want to know which experiences require reservations. But research gives me choices. It doesn’t mean I have to complete a checklist. Once I’m there, I get to change my mind. In fact, it doesn’t mean I even have to do any of those things; it only means that I have possibilities.
Rest is allowed to be part of the experience
Somewhere along the way, we learned to treat a nap on vacation as though we’d failed. While I’m NOT a napper (I never learned how to nap without it ruining my sleep, but my husband is really good at it). I strongly disagree. A pause in a beautiful hotel, a quiet hour on a balcony or a slow morning over coffee can be exactly what makes the rest of the day enjoyable.
This matters even more on a long trip. One energetic day after another sounds appealing when you’re planning from home. It can feel very different after flights, changing time zones, unfamiliar beds, and miles of walking. Slowing down for an afternoon isn’t wasting the trip. It’s listening to yourself so you can enjoy the evening, too.
If I have a special dinner planned, I don’t need to spend the afternoon racing from one end of a city to the other. I might return to the hotel, take my time getting ready, and make the dinner the occasion it deserves to be. The anticipation is part of the pleasure.
The people you’re with need room, too
Doing less can make a trip better for everyone, especially when you’re traveling with family or friends. Not everyone wants to get up at the same hour, walk the same distance, or linger in the same places. One person may want a museum while another would happily spend the morning at the pool.
There’s no rule that says you must experience every minute together. Agree on the moments you want to share, then let people enjoy some time in their own way. Meet for lunch and tell each other what you discovered. That conversation might be more fun than dragging a reluctant companion through an attraction neither of you ends up enjoying. When my brother and I travel, we usually have a little breakfast together and agree to meet for dinner. At breakfast we might go over our individual plans (from museums to absolutely nothing) and if the other wants to go as well, we go together. Sometimes that works; other times, he’s at the museum and I’m meandering through a farmer’s market taking in the colors and smells.
When grandchildren are involved, a little breathing room becomes even more valuable. A child may be thrilled by the pool, a boat ride, or an ice cream stop long after the adults have decided the “big” attraction is over. You don’t have to fill every hour to make a memory with them. Sometimes you only have to stay a little longer.
My ritual for a lighter itinerary
Before a trip, I write down the experiences I would truly regret missing. It’s usually a much shorter list than the one I started with. I book the things that need to be booked, check opening hours and travel time, and then look at the days as a whole. Have I allowed time to get from one place to another without rushing? Is there a slower day after a particularly busy one? Have I left space for a meal that lasts longer than expected?
Then I keep a second list: things I could do. A market, an art gallery, a walking route, a shop, a restaurant. That list is there when I want inspiration. It isn’t homework. This is where my vacation usually starts to shine.
Most of all, I try to remember why I wanted to take the trip in the first place. If it was to reconnect with someone, I make time to talk. If it was to rest, I protect the quiet hours. If it was to discover a new place, I leave a little room to get lost in it, at least figuratively. I do still check the route back to the ship!
There will always be something you don’t see. Another museum, another beach, another restaurant, another street around the corner. That doesn’t mean you missed your vacation. It means the world is bigger than any itinerary you may have planned.
These days, when I come home, I don’t measure a trip by how many things I crossed off a list. I think about how I felt while I was there. I want to remember the view, the conversation, and the unexpected moment I had time to notice.
That, to me, is the art of doing less. And somehow, it lets me bring more home from each trip than I had initially “planned.”
