10 Ways to Plan for a Better Trip

In 12 Ways to Be More Spontaneous When You Travel, I offered tips for planning types to add a bit more flexibility to their travels. After all, the most memorable travel episodes are often more about the surprises you encounter than the well-planned and almost predictable notches on your tourism belt. Travelers who script out each day are leaving themselves less open to these unexpected experiences.

On the other hand, there is a breed of traveler who is inclined to plan out almost nothing. These folks are fewer in number these days than just a couple of decades ago, I would posit, mainly due to the incredible ease of gathering information on almost any destination in the world. Even for the type of person who considers travel planning an odious chore, doing a few searches on the Internet is now so easy that it doesn’t even feel like effort.

But they are out there, and even a little planning can go a long way to help these folks get the most from their travels. Below are 10 practicable tips on how spontaneous folks can enhance their travels by doing a bit more planning than comes naturally.

1. Leave the first day absolutely open.

A sense of freedom is an important part of the travel experience for many independent travelers, so starting off your trip with a wholly freewheeling, unscheduled day will bring on these sensations immediately. As a spontaneous traveler, you are playing to your strengths and preferences right from the start, so even if you start buying timed museum tickets and making dinner reservations the very next morning, a critical first free day can satiate your natural urges for a while, and not leave you feeling like you have been overscheduled since the moment you arrived.

2. Do a self-determined “orientation” tour.

I have done something like this in a couple of major cities: on my first day in town, I rented a bike, got a tourist map and hit the streets. As you cruise past each attraction, you can get a much stronger sense of the places you really want to visit as compared to seeing pictures and reading reviews. Along the way, you get a feel for the rhythms of a place, which is an essential part of travel that can’t be underestimated.

If you can’t do it by bike, try public transportation or walking, or even better a combination of the two. You will want to scope out any unsafe neighborhoods or routes, but overall it is a very freewheeling way to give yourself a quick orientation in almost any destination.

3. Alternatively, take a guided tour early in your trip.

While many independent travelers find these tours utter anathema, hear me out. Taking a guided tour can help in at least a couple of ways.

First, it can give you some orientation as to where things are, how crowded they are, how “touristy” they are and if they live up to their billing. Then you can decide if they are worth your effort to plan a visit.

Second, it can help you tick off a few of the things you (or friends, or guidebooks, or websites) feel are absolutely must-see. These are often historical buildings, statues and monuments that are seen just as well from a bus window or boat deck as not; even if you want to go inside for a quick look, hop-on/hop-off bus tours allow for this in many locations.

These could be bus tours in New York, a boat tour in Amsterdam or a Segway tour in Berlin. It is a fast and easy (and often affordable) way to dispatch all the “important” stuff so you can start wandering the town in search of adventure.

4. Get (up) high.

A personal tactic I have used now and then is to plan an early visit to a location with ridiculously good views, such as the Eiffel Tower in Paris, the Panoramapunkt in Berlin, or Rockefeller Center or the Empire State Building in New York. Inevitably there are neighborhoods or attractions that will catch your eye, and having had an aerial view already, can even make a little bit more sense when you return to the streets.

Travel Smarter! Sign up for our free newsletter.

By proceeding, you agree to our Privacy Policy and Terms of Use.

Sign Up

5. Pick three things, and schedule those.

In any given trip to any given city, there are likely to be two or three things that you really shouldn’t miss. Read a guidebook, a “10 Essential Things” article or the like, and pick three things from it to schedule. If you come up with more than three things, talk it out with your travel mates, see where your interests overlap the most and then return to the list to narrow it down again.

Limiting yourself in this way can be very powerful; in fact, it is probably something I should have recommended to planners.

6. Pocket the rest.

Once you pick your top three attractions, pocket the rest of them as a B list of things to do if you hit a lull in your day, you just happen to be near one by happenstance, you find long lines at one of your top three or you get advice from a local that one of them is a must-see. In this way, visiting even the main attractions can become spontaneous events in your travel meanderings, a win-win for you.

7. Check for big events like festivals and concerts.

Checking city event calendars before you leave to discover any major events can help in a couple of ways. First, it might help you find something you would really like to attend. Second, it might alert you to something you would really like to avoid.

In the former case, there might be a really appealing festival or concert going on that will sell out in advance. While some events you can simply show up to, you’ll want to buy tickets ahead of time if you know the demand is high.

In the latter case, big events like festivals, parades and major concerts or sporting events always bring crowds, traffic, parking challenges, and higher hotel and car rental rates. If you know what is happening, you can usually plan around these challenges.

8. Check attraction schedules and ticketing procedures.

While it sounds great simply to drop into an attraction whenever you happen to be nearby, it’s not that easy if the place is closed or if it requires reservations or online tickets. As you make your A and B lists of attractions, make a note of how easy they are to visit, whether they have extended hours, if they are closed on certain days of the week (many museums are closed on Mondays, for example) and if you can buy open-ended tickets that will save you time in lines but don’t require you show up at a specific time. This way you can keep things loose without getting shut out of very popular attractions.

9. Visit popular attractions at off-hours.

Outdoor fountains or churches at night, museums as soon as they open and before the crowds arrive, famous street markets just after dawn while the vendors are still setting up — all of these give you a different look at even the most well-trodden sites. Plan these into your sightseeing schedule to make even the most rote visit on the tourist trail seem interesting and adventurous.

10. Leave the last day open.

When your trip is over, if the last thing you did was a forced march through suggested sites, you may get home feeling like you need a day off to recover from your week off. Notching off museums, making scheduled entry times and generally doing things that are expected of you feels all too much like work. And for sure the trip home feels that way, so making your last day loose and free can really help.

So make the last day a play day, a lazy day, a day off — however you want to think about it. That way when you do get home and have to go back into your routine, at least it has been a few days since you had to toe the line and please the man.

Have any tips to help spontaneous travelers get more from their travels by succumbing to a bit of planning? Please add them in the comments!