A Simple Traveler's Guide to a Day Trip

If I had my way, every time I traveled somewhere new I'd be able to spend weeks or months exploring all the nooks and crannies of every space in that wonderful city or town. Unfortunately, due to limited time and limited money, that is generally not the case. 

Over the last three years, I've been to nearly a dozen new places and for over half of those trips, I've only had one day to explore the particular place I was visiting.

 
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If you like to travel simply and not pack too much into your schedule, day trips can seem like the worst possible option. How could you possibly fit all of the "must do" and "must see" things for a city like Chicago or Charleston into a single day? How can you take your time exploring the city, but still see as much as you're able to?

While I don't claim to be an expert, with my excessive number of day trips over the last few years, I've learned a thing or two about making the most of a mere 8-16 hours in a single city without completely overwhelming or exhausting yourself.

START WITH A QUESTION

Every time I'm heading somewhere new, especially when it's my first time in a city, I start by posing a question to anyone who will answer it — if I only have one day to explore the city, what are the must do or see things and must eat places?

Invariably, the recommendations you receive from people will be all over the place and what one person considers "must see" can vary dramatically from what another person considers "must see." The point of this exercise isn't to give you a defined itinerary for your day in a new city, but to give you a starting point.

You could accomplish the same thing by Googling a similar question, but I find the personal touch of hearing from people you actually know gives a higher quality of recommendations. You'll often wind up with recommendations that would be great for the masses, along with a few specific recommendations that most other people wouldn't care about, but you as an individual would absolutely love.

Depending on where you're going, you may have a lot of different recommendations, but don't allow that to overwhelm you! Remember that for big cities like New York or Washington DC, it is literally impossible to see it all in one day, so don't make that your goal!

CONSIDER YOUR PERSONAL INTERESTS

Once you've got a list of recommendations as a starting point, take a step back and consider your personal interests.

Are you a major foodie who loves tasting local cuisine? Do you love architecture or history? Quirky art galleries or off-the-beaten path museums? Every city is going to have things that some people consider "must see" but you probably don't care that much about, so it's important to identify what you love to see in general, not just based on what a specific city has to offer.

For example, I'm not really a food person. I enjoy food, of course, but I am also totally fine being that person who goes to Panera or Starbucks no matter what city I go to if necessary. This doesn't mean that I totally discount recommendations for "must eat" places, but I'm probably only going to prioritize one or two of them, rather than planning my trip around the places I'm going to eat like other people I know.

If you love museums or architecture or history, focus on the parts of the city that will give you the most of those, even if it's not what everyone else considers a "must see."

DESIGNATE YOUR TOP THREE

Unless you're going to a relatively small area that doesn't have a lot to do, even after you've narrowed your list down by taking personal interests into account, you'll probably wind up with a pretty lengthy list of things to go do or see. Your list as it stands is probably either an impossibility, or would result in a trip that leaves you completely exhausted and unable to fully appreciate this wonderful new place you're exploring.

That's why I always recommend people designate their top three priorities. No matter how big or small the city or place you're visiting is, look through all those recommendations and things you've pared it down to and ask yourself what three things you would be the most sad to miss if you never go to go back to that city again.

It's important to note that you should account for time when considering those top three things. If your top three things would all take a half or full day to explore, then you're going to need to do a little reevaluation.

For example, I recently visited New Orleans for the first time and several people recommended I go to the World War II Museum. Ordinarily, this would be high on my list of priorities because history museums are one of my favorite things to explore in a new city. But everyone I talked to said the museum is the kind of place that you really want to spend at least a half day, if not a full day in. Since I had a few other priorities on my list, I knew I wouldn't be able to dedicate the time I really wanted to exploring that museum without neglecting everything else I wanted to see, so I decided to hold off on it for another trip.

FILL IN THE REST OF YOUR ITINERARY

Once you've designated those top three (doable) priorities, it's time to fill in the rest of your itinerary.

Depending on what those top three things are, your itinerary may be complete and you may just have to decide the particular order you want to see those things in. But you may also still have room in your schedule for some secondary priorities without making the day too exhausting or overwhelming.

If you're not someone who plans your trips around food, this is the perfect place to add in those restaurants you might want to visit. Consider where certain restaurants are in relation to the other things you'll be seeing and doing, and figure out which ones would be most convenient for you to visit without taking you too far off the path from the things that are priorities for you.

BE FLEXIBLE

Finally, the best way to have an enjoyable and relaxing day trip to a new city is to just be flexible. 

Remember that you aren't going to be able to see everything and that's perfectly okay. The weather may wind up messing up some of your plans if a few of your activities involve the outdoors, or you may be in the city on the day something you'd love to visit is closed. Keep a list of back-up places on your phone and allow yourself to just go with the flow.

I've always found I enjoy day trips more when I go in with a small list of "must dos," an extra list of "it would be cool to see this" things, and an open mind about what my day is going to look like. This has been my attitude with the last several cities I've visited by day trip and I've yet to be disappointed.