March 16

Planning Vs. Going With The Flow – Tips On Structuring (Or Not) Your Travels


[pullquote align=”normal”]Did you ever regret booking the RTW ticket? Obviously you got an incredible deal, but did you miss the flexibility of going somewhere you didn’t originally intend, or meeting people and tagging along with them to their next destination? [/pullquote]

This is a great question I get asked often and it's something I also wrestled with as I was planning my trip.

The idea of an open-ended trip leaves your mind wondering with the mystery of endless possibilities, while planning it all out feels stable, but also exciting, because you can look forward to all the adventures you've planned.

Even though I've been living on the road out of a backpack since the end of 2012, I still don't have a definitive answer for you. All I can say is: it depends.

There are three basic methods when it comes to traveling: planning, going with the flow, and "The Skeleton."

The Skeleton is a mix of planning and going with the flow, which I inadvertently stumbled on as I traveled. It worked really well for me, but mostly because I was traveling for such a long period to many different cities and countries.

All three types of traveling have their advantages and disadvantages depending on what type of travel you're doing and what type of person you are.

I'll be breaking down each method and discussing some of the advantages and disadvantages of each, to help you when you're wrestling with this issue for your next trip.

I'll discuss:

  • How going with the flow can save you money.
  • The aspects of a trip I always plan, and why.
  • How "The Skeleton" motivated me to make the most of my travels

Should You Plan Or Go With The Flow When You Travel?

Click to Tweet

The Skeleton

As I said above, this is what I have dubbed my planning strategy when I traveled around the world for a year.

I decided to call the strategy "The Skeleton" because when I outlined my trip I only booked the 15 flights to take me around the world.

It was the foundation of the trip, or a skeleton, with the idea to flesh out the trip as I landed in each of the locations.

When I planned out the initial flights, I made sure to give myself plenty of time in each location, which would allow me the flexibility to go somewhere unexpected and play with the open-ended type of travel.

For example, I was in Singapore for 3.5 weeks, and as I met and talked with other travelers about what there was to do, I uncovered how cheap and easy it was to get to Bali, Indonesia.

I bought a plane ticket out to Bali and had an amazing adventure there for 2 weeks before flying back to Singapore.

It was a spontaneous trip I was able to make happen because I had enough time to get settled in, pick other travelers' brains and make plans.

This would happen many more times throughout the year with spectacular results.

However, one issue I often have while traveling long-term are instances where I'll think: "I could stay here for so much longer."

What then?

Since I had already pre-purchased my flights, I didn't really have a choice, which was both a blessing and a curse.

In a perfect world, I'd never have to deal with this, but I only had so much money.

The skeleton helped keep me motivated to make the most of my time in each place.

Furthermore, after I reflected on the entire trip, I found even though there were many times I felt like I was leaving a place too early for my liking, I went on to have an amazing experience somewhere else I wouldn't have had, had I stayed in the original location.

It was a good lesson in letting go of the comfortable to explore the unknown.

Pre-Purchasing Major Flights


  • Removes Budgeting - Since the flights were purchased I didn't have to worry about budgeting money to get to the next destination.
  • Less Stress - I didn't have to worry about trying to hunt down deals while on the road or worry about lackluster internet.
  • Motivating - Because I knew how long I had in each place, it made it easier to make the most of my time there. I still had relaxing days, but I find when I travel in an open-ended style, I get complacent and find myself saying, "I have plenty of time, I'll do [activity] tomorrow."


  • Circular Travel - Because I traveled on a RTW Ticket, I flew into and out of the same city. This was annoying because I constantly had to travel in a circle, instead of A to B to C to D.
  • Time Consuming/Expensive - You have to save up more money (or spend a lot of time travel hacking) beforehand to purchase the tickets, as opposed to arriving and finding a job while you experience the culture and saving up money for the next leg of the trip. 

Overall, I think The Skeleton is a great strategy for long term travel (over 3 months) where you're going to be traveling around to a few different countries.

I like it because it was the best of both worlds--It gave me enough structure to make sure I never stayed in one place too long, but also allowed me to go with the flow when an awesome and unexpected opportunity presented itself.

I also eliminated the large and stressful variable of airline price fluctuations, which can really mess up a tight budget.


Planning will always have a special place in my heart due to my A-type personalty, and there are some aspects of a trip I'll always plan out in advance.

A Place To Stay & Direction On How To Get There​

I've learned from experience, when I arrive somewhere new (especially when there's a language barrier) and I'm tired, hungry and thirsty, the last thing I want to do is try and find somewhere to sleep for the night.

I've found this situation is much less enjoyable than dealing with a crappy hostel in a crappy area.

When I book a place to stay I usually only book two nights.


There's a chance the hostel will be bad for any number of reasons.

But, with the two nights, I can get settled in and recharge, get a map of the area, use the wi-fi and talk to other travelers to find better options without having to worry about losing much money due to deposits/cancellation charges.

And if the hostel turns out to be great, booking two nights gives me enough of a buffer where I can extend my stay without worrying too much they'll be booked up, and if they are booked up, the two nights gives me enough of a buffer to find a new place.

Adventures I REALLY Want To Do

If there's an activity in a country you really want to see and you only have a limited time there, it makes sense to book the activity beforehand (especially if you're going during busy season).

This way you make sure you have a spot and you'll get to experience your adventure.

If you're taking the time to plan and book out activities in advance you should also make sure you can get to the activity.

I imagine your spirits would take a quick turn for the worse if you're on the way to an adventure of a lifetime only to show up to the train station and find your train sold out.

Besides these two aspects of a trip, I pretty much leave everything else open-ended when I travel these days.

However, because planning is a great way to maximize your travel time by preventing researching and planning while you're on the road, there are certain trips and situations where I think planning a majority of the trip out beforehand can be a good strategy:

When Planning Is A Good Strategy

  • Shorter Trips (<10 Days)
  • Less Experienced Travelers
  • Traveling In A Group
  • Hardcore A-Type Personality

Going With The Flow

When Flowing Is A Good Strategy

  • Longer Trips (>10 Days) To One Country/City
  • Traveling On A Tight Budget
  • B-Type Or Outgoing Personality

If the above fits you, I think going with the flow is a great strategy.

Not only do you keep yourself open for adventures--like meeting a girl on the side of the road who invites you on an unexpected adventure, but you can also save money when you travel this way.

How? Three main ways.

Last Minute Discounts

This works best when you're in a country during their off season or during the middle of the work week.

Often you can show up the day of or a few days before a tour is leaving and find tours with a few seats left.

The bus is for sure going but they'd stand to make more money if they could fill the rest of the seats.

Usually the company will already be offering a discounted rate to fill the last few seats, but if not, you can very easily offer the win-win scenario yourself.

This is how I was able to save $100 when I scuba dived The Great Barrier Reef.

Buying Local & Haggling

When you look up and book activities online beforehand, you're limiting yourself to companies that can afford the creation/maintenance of a website and they usually charge more.

When you arrive in the city where you want to do your activity, you can usually find an area of town with many different companies offering the same product.

You'll usually find the prices in person to be cheaper than what you were finding online.

If you really enjoy trying to get the best deal you can walk around to a few different companies and find out their prices.

Sometimes you might find a cheaper price, for example, I find companies without a prime location often have cheaper prices than the companies with offices in the town center.

When you have a lot of price information, you can use it to try and negotiate a cheaper price.

"Your [product] costs $50? The company on the corner is only charging $40."

You don't need to lie or yell, just state the facts. This will at least get you a price match.

Then you can decide if you want to try and haggle.

If you do decide to haggle, your goal should be to create win-win scenarios. If a deal is made and one party feels cheated or taken advantage of, you're doing it wrong.

"You'll do $40 now, too? Ok, If you go down to $30 I'll go with your company."

Many times I'll get a "no" until I turn around to leave, and then I'll get the green light or a counter offer.

Sometimes you'll get it, sometimes you won't, if anything, you'll get some good negotiation practice.

Instead of buying bus tickets online while I was in South America I'd always go to the bus station to buy them. The tickets were always cheaper than the prices advertised online and I could also shop around the different companies to find the most affordable price.

Forming A Group With Other Travelers

Going with the flow gives you a great opportunity to meet other travelers, especially if you're staying in hostels.

Talk with these travelers and figure out what they are planning on doing.

Does it sound cool? Cool. You're in, and now you're a party of two.

Ask around, and try to turn your party of two into a group.

With your new, nifty group formed you can ask for discounts on tour packages because of how many people are signing up at once.

Or you can be even more adventurous, split a car rental and make your own tour, which can be quite cheap when you're splitting everything 4-5 ways.

Renting a car myself while I was on Easter Island was way out of my budget, however, using this strategy, I found four other people in the hostel to go in on a car rental, which allowed us to tour the entire island and see all of the Moai at a much more affordable price.

Which Method Is Right For You?

Each method of travel has its advantages and disadvantages and as you travel more you'll figure out which style or combination of styles works best for you.

Do you sleep better knowing everything is set and booked or do you enjoy being open to the mystery waiting to be unlocked?

Some people hate having to wake up every morning and spend time trying to figure out what to do, thus potentially missing out on great experiences due to lack of organization.

Some people enjoy serendipity and the flexibility to take advantage of unexpected opportunities and discover hidden gems.

Luckily, there's no right or wrong way to travel as long as you get out there and are enjoying yourself.


You may also like

2021 Yearly Review

2021 Yearly Review
{"email":"Email address invalid","url":"Website address invalid","required":"Required field missing"}