For a long time, I’ve had the luxury of traveling at my own speed. Whether it’s two days or two months, I’ve always had the time I needed. I’ve always believed that when it comes to travel, less is more. It’s better to dive deep into a few places than to skim the surface of many. This way, you get to know the people and places better, and you avoid the stress and expense of constant travel.
I get it, when you only have a few weeks a year to travel, you want to see as much as possible. But I’ve always advised against this. You end up spending too much time moving from place to place, packing and unpacking. I once tried to see most of Dublin in a day, and it was just crazy.
In March, I visited San Francisco for the first time as part of my book tour. I only had 3.5 days in the city and, unlike most trips, I had to squeeze everything into a short time. I knew I’d only scratch the surface, but I figured something was better than nothing.
What did I learn from this experience? Three days is not nearly enough. I was rushing around to see the major sights, trying to fit in the best restaurants, getting tired from walking up all those hills, and just feeling exhausted from always being on the go. Trying to see everything in just a few days was a nightmare. Everything becomes a blur, and you end up with photos instead of memories.
I left San Francisco with two realizations: (1) I need to go back because what I saw was amazing, and (2) there has to be a better way to travel short-term than running around like a headless chicken.
My trip to Lisbon gave me a chance to find a better way. I only had three days again, but I was determined not to repeat my San Francisco experience. This time, I came with a plan. I didn’t schedule every second of every day. Travel is about letting things happen naturally, not planning every moment. But I wanted to leave Lisbon without feeling exhausted and without feeling like I hadn’t seen anything.
Having a rough idea of what I wanted to see and do before I went allowed me to prepare, organize my visit, and pace myself. I missed a lot of stuff the first time I was in the city last year. I decided that on the first day I would explore the city center, visit the history museum, and see Sé Cathedral and São Jorje Castle. On the second day, I would go to the beach outside of town. On the third day, I would take a city walking tour offered by the hostel, visit the lookout tower, and explore a few other churches.
Despite being super jet-lagged and sleeping through much of the first day, I found that having a plan allowed me to see most of what I wanted without feeling like I was rushing around. I was able to see what I wanted while still finding time to add in local recommendations. And while I rearranged the order of everything when I got into town, by breaking up the days into manageable chunks, I found I could explore at a relaxed pace.
I used the same strategy when I was in Madrid a few days later, with the same results. I had four days in town, and I started with a plan. I made a list of all the sights in Madrid that I wanted to see and then each day went through that list: botanical gardens, food tour, walking tour, art museums, nightlife, cathedral, and the royal palace. I didn’t get to everything, but I found that having a list helped set a pace that made exploring a big city in a few days seem less overwhelming.
So, what’s the takeaway? If you’re trying to explore somewhere new and only have a short time to see it, it’s best to go in with a rough itinerary to make the most of your limited time. By doing some preliminary planning, you can avoid feeling overwhelmed and instead focus on actually enjoying your trip, seeing what you want, and still finding time to let the road take you to interesting places.
I get a lot of emails asking for help with itineraries and hour-by-hour planning for trips, and I see a lot of people trying to cram too much into a short time. In my experience, however, creating a framework for your trip instead — and filling in the smaller details along the way — is a much more relaxing way to not only plan a trip but also see your destination.
